Flights from Chicago to Italy (MDW to IT)

Discover alternate routes and cheaper dates from Chicago to Italy (MDW to IT) within a date range.

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  • US$796
    Frontier AirlinesNorse Atlantic UKWizz Air Malta
    10:00pm - 12:30am
    Wed Mar 5th 2025
    43h 30m
    Chicago (MDW) → Rome (FCO)
    2 Stops

    Wed Mar 5th 2025 Frontier Airlines · F9 2329 Depart at 10:00pm from Chicago (MDW) Fly for 3h 59m Arrive at 11:59pm in Las Vegas (LAS)

    Layover in Las Vegas for 16h 46m

    Thu Mar 6th 2025 Norse Atlantic UK · Z0 778 Depart at 4:45pm from Las Vegas (LAS) Fly for 9h 50m Arrive at 10:35am in London (LGW)

    Layover in London for 10h 25m

    Fri Mar 7th 2025 Wizz Air Malta · W4 6004 Depart at 9:00pm from London (LGW) Fly for 2h 30m Arrive at 12:30am in Rome (FCO)

  • US$798
    Frontier AirlinesNorse Atlantic UKWizz Air Malta
    2:54pm - 12:30am
    Thu Mar 6th 2025
    26h 36m
    Chicago (MDW) → Rome (FCO)
    2 Stops

    Thu Mar 6th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 2h 10m

    Thu Mar 6th 2025 Norse Atlantic UK · Z0 784 Depart at 8:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 11h 0m

    Fri Mar 7th 2025 Wizz Air Malta · W4 6004 Depart at 9:00pm from London (LGW) Fly for 2h 30m Arrive at 12:30am in Rome (FCO)

  • US$798
    Frontier AirlinesNorse Atlantic UKWizz Air Malta
    11:38am - 12:25pm
    Mon Mar 24th 2025
    42h 47m
    Chicago (MDW) → Venice (VCE)
    2 Stops

    Mon Mar 24th 2025 Frontier Airlines · F9 1458 Depart at 11:38am from Chicago (MDW) Fly for 2h 41m Arrive at 3:19pm in Orlando (MCO)

    Layover in Orlando for 6h 36m

    Mon Mar 24th 2025 Norse Atlantic UK · Z0 784 Depart at 9:55pm from Orlando (MCO) Fly for 8h 5m Arrive at 10:00am in London (LGW)

    Layover in London for 23h 15m

    Wed Mar 26th 2025 Wizz Air Malta · W4 6702 Depart at 9:15am from London (LGW) Fly for 2h 10m Arrive at 12:25pm in Venice (VCE)

  • US$803
    Frontier AirlinesPlayWizz Air Malta
    3:28pm - 1:10am
    Wed Mar 19th 2025
    51h 42m
    Chicago (MDW) → Rome (FCO)
    2 Stops

    Wed Mar 19th 2025 Frontier Airlines · F9 3088 Depart at 3:28pm from Chicago (MDW) Fly for 1h 51m Arrive at 6:19pm in Washington, D.C. (BWI)

    Layover in Washington, D.C. for 24h 46m

    Thu Mar 20th 2025 Play · OG 102 Depart at 7:05pm from Washington, D.C. (BWI) Fly for 6h 0m Arrive at 5:05am in Reykjavik (KEF)

    Layover in Reykjavik for 14h 20m

    Fri Mar 21st 2025 Wizz Air Malta · W4 6098 Depart at 7:25pm from Reykjavik (KEF) Fly for 4h 45m Arrive at 1:10am in Rome (FCO)

  • US$824
    Frontier AirlinesNorse Atlantic UKVueling
    10:00pm - 12:10am
    Mon Mar 10th 2025
    44h 10m
    Chicago (MDW) → Rome (FCO)
    2 Stops

    Mon Mar 10th 2025 Frontier Airlines · F9 2329 Depart at 10:00pm from Chicago (MDW) Fly for 3h 59m Arrive at 11:59pm in Las Vegas (LAS)

    Layover in Las Vegas for 17h 46m

    Tue Mar 11th 2025 Norse Atlantic UK · Z0 778 Depart at 5:45pm from Las Vegas (LAS) Fly for 9h 50m Arrive at 10:35am in London (LGW)

    Layover in London for 10h 15m

    Wed Mar 12th 2025 Vueling · VY 6225 Depart at 8:50pm from London (LGW) Fly for 2h 20m Arrive at 12:10am in Rome (FCO)

  • US$826
    Frontier AirlinesNorse Atlantic UKWizz Air Malta
    10:00pm - 10:55pm
    Wed Mar 5th 2025
    41h 55m
    Chicago (MDW) → Naples (NAP)
    2 Stops

    Wed Mar 5th 2025 Frontier Airlines · F9 2329 Depart at 10:00pm from Chicago (MDW) Fly for 3h 59m Arrive at 11:59pm in Las Vegas (LAS)

    Layover in Las Vegas for 16h 46m

    Thu Mar 6th 2025 Norse Atlantic UK · Z0 778 Depart at 4:45pm from Las Vegas (LAS) Fly for 9h 50m Arrive at 10:35am in London (LGW)

    Layover in London for 8h 35m

    Fri Mar 7th 2025 Wizz Air Malta · W4 6902 Depart at 7:10pm from London (LGW) Fly for 2h 45m Arrive at 10:55pm in Naples (NAP)

  • US$829
    Frontier AirlinesNorse Atlantic UKWizz Air Malta
    2:54pm - 10:55pm
    Thu Mar 6th 2025
    25h 1m
    Chicago (MDW) → Naples (NAP)
    2 Stops

    Thu Mar 6th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 2h 10m

    Thu Mar 6th 2025 Norse Atlantic UK · Z0 784 Depart at 8:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 9h 10m

    Fri Mar 7th 2025 Wizz Air Malta · W4 6902 Depart at 7:10pm from London (LGW) Fly for 2h 45m Arrive at 10:55pm in Naples (NAP)

  • US$829
    Frontier AirlinesNorse Atlantic UKWizz Air Malta
    11:38am - 12:30am
    Mon Mar 24th 2025
    30h 52m
    Chicago (MDW) → Rome (FCO)
    2 Stops

    Mon Mar 24th 2025 Frontier Airlines · F9 1458 Depart at 11:38am from Chicago (MDW) Fly for 2h 41m Arrive at 3:19pm in Orlando (MCO)

    Layover in Orlando for 6h 36m

    Mon Mar 24th 2025 Norse Atlantic UK · Z0 784 Depart at 9:55pm from Orlando (MCO) Fly for 8h 5m Arrive at 10:00am in London (LGW)

    Layover in London for 11h 0m

    Tue Mar 25th 2025 Wizz Air Malta · W4 6004 Depart at 9:00pm from London (LGW) Fly for 2h 30m Arrive at 12:30am in Rome (FCO)

  • US$839
    Frontier AirlinesNorse Atlantic UKWizz Air Malta
    2:54pm - 11:25pm
    Thu Mar 20th 2025
    26h 31m
    Chicago (MDW) → Milan (MXP)
    2 Stops

    Thu Mar 20th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 3h 10m

    Thu Mar 20th 2025 Norse Atlantic UK · Z0 784 Depart at 9:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 10h 25m

    Fri Mar 21st 2025 Wizz Air Malta · W4 6304 Depart at 8:25pm from London (LGW) Fly for 2h 0m Arrive at 11:25pm in Milan (MXP)

  • US$845
    Frontier AirlinesNorse Atlantic UKWizz Air Malta
    2:54pm - 12:30am
    Thu Mar 20th 2025
    27h 36m
    Chicago (MDW) → Rome (FCO)
    2 Stops

    Thu Mar 20th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 3h 10m

    Thu Mar 20th 2025 Norse Atlantic UK · Z0 784 Depart at 9:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 11h 0m

    Fri Mar 21st 2025 Wizz Air Malta · W4 6004 Depart at 9:00pm from London (LGW) Fly for 2h 30m Arrive at 12:30am in Rome (FCO)

  • US$847
    Frontier AirlinesNorse Atlantic UKVueling
    11:38am - 6:00pm
    Mon Mar 24th 2025
    24h 22m
    Chicago (MDW) → Florence (FLR)
    2 Stops

    Mon Mar 24th 2025 Frontier Airlines · F9 1458 Depart at 11:38am from Chicago (MDW) Fly for 2h 41m Arrive at 3:19pm in Orlando (MCO)

    Layover in Orlando for 6h 36m

    Mon Mar 24th 2025 Norse Atlantic UK · Z0 784 Depart at 9:55pm from Orlando (MCO) Fly for 8h 5m Arrive at 10:00am in London (LGW)

    Layover in London for 4h 55m

    Tue Mar 25th 2025 Vueling · VY 6207 Depart at 2:55pm from London (LGW) Fly for 2h 5m Arrive at 6:00pm in Florence (FLR)

  • US$847
    Frontier AirlinesPlayWizz Air Malta
    3:28pm - 1:10am
    Mon Mar 10th 2025
    51h 42m
    Chicago (MDW) → Rome (FCO)
    2 Stops

    Mon Mar 10th 2025 Frontier Airlines · F9 3088 Depart at 3:28pm from Chicago (MDW) Fly for 1h 51m Arrive at 6:19pm in Washington, D.C. (BWI)

    Layover in Washington, D.C. for 24h 46m

    Tue Mar 11th 2025 Play · OG 102 Depart at 7:05pm from Washington, D.C. (BWI) Fly for 6h 0m Arrive at 5:05am in Reykjavik (KEF)

    Layover in Reykjavik for 14h 20m

    Wed Mar 12th 2025 Wizz Air Malta · W4 6098 Depart at 7:25pm from Reykjavik (KEF) Fly for 4h 45m Arrive at 1:10am in Rome (FCO)

  • US$851
    Frontier AirlinesNorse Atlantic UKeasyJet
    2:54pm - 5:40pm
    Thu Mar 6th 2025
    19h 46m
    Chicago (MDW) → Turin (TRN)
    2 Stops

    Thu Mar 6th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 2h 10m

    Thu Mar 6th 2025 Norse Atlantic UK · Z0 784 Depart at 8:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 4h 50m

    Fri Mar 7th 2025 easyJet · U2 8359 Depart at 2:50pm from London (LGW) Fly for 1h 50m Arrive at 5:40pm in Turin (TRN)

  • US$855
    Frontier AirlinesNorse Atlantic UKWizz Air Malta
    2:54pm - 11:25pm
    Thu Mar 6th 2025
    25h 31m
    Chicago (MDW) → Milan (MXP)
    2 Stops

    Thu Mar 6th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 2h 10m

    Thu Mar 6th 2025 Norse Atlantic UK · Z0 784 Depart at 8:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 10h 25m

    Fri Mar 7th 2025 Wizz Air Malta · W4 6304 Depart at 8:25pm from London (LGW) Fly for 2h 0m Arrive at 11:25pm in Milan (MXP)

  • US$857
    Frontier AirlinesNorse Atlantic UKVueling
    2:54pm - 12:10am
    Thu Mar 20th 2025
    27h 16m
    Chicago (MDW) → Rome (FCO)
    2 Stops

    Thu Mar 20th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 3h 10m

    Thu Mar 20th 2025 Norse Atlantic UK · Z0 784 Depart at 9:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 10h 50m

    Fri Mar 21st 2025 Vueling · VY 6225 Depart at 8:50pm from London (LGW) Fly for 2h 20m Arrive at 12:10am in Rome (FCO)

  • US$858
    Frontier AirlinesNorse Atlantic UKWizz Air Malta
    2:54pm - 10:55pm
    Thu Mar 20th 2025
    26h 1m
    Chicago (MDW) → Naples (NAP)
    2 Stops

    Thu Mar 20th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 3h 10m

    Thu Mar 20th 2025 Norse Atlantic UK · Z0 784 Depart at 9:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 9h 10m

    Fri Mar 21st 2025 Wizz Air Malta · W4 6902 Depart at 7:10pm from London (LGW) Fly for 2h 45m Arrive at 10:55pm in Naples (NAP)

  • US$864
    Frontier AirlinesNorse Atlantic UKeasyJet
    2:54pm - 3:55pm
    Thu Mar 6th 2025
    18h 1m
    Chicago (MDW) → Rome (FCO)
    2 Stops

    Thu Mar 6th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 2h 10m

    Thu Mar 6th 2025 Norse Atlantic UK · Z0 784 Depart at 8:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 2h 30m

    Fri Mar 7th 2025 easyJet · U2 6506 Depart at 12:30pm from London (LGW) Fly for 2h 25m Arrive at 3:55pm in Rome (FCO)

  • US$864
    Frontier AirlinesNorse Atlantic UKeasyJet
    2:54pm - 5:20pm
    Thu Mar 6th 2025
    19h 26m
    Chicago (MDW) → Verona (VRN)
    2 Stops

    Thu Mar 6th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 2h 10m

    Thu Mar 6th 2025 Norse Atlantic UK · Z0 784 Depart at 8:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 4h 20m

    Fri Mar 7th 2025 easyJet · U2 8335 Depart at 2:20pm from London (LGW) Fly for 2h 0m Arrive at 5:20pm in Verona (VRN)

  • US$865
    Frontier AirlinesNorse Atlantic UKeasyJet
    2:54pm - 5:40pm
    Thu Mar 20th 2025
    20h 46m
    Chicago (MDW) → Turin (TRN)
    2 Stops

    Thu Mar 20th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 3h 10m

    Thu Mar 20th 2025 Norse Atlantic UK · Z0 784 Depart at 9:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 4h 50m

    Fri Mar 21st 2025 easyJet · U2 8359 Depart at 2:50pm from London (LGW) Fly for 1h 50m Arrive at 5:40pm in Turin (TRN)

  • US$865
    Frontier AirlinesNorse Atlantic UKeasyJet
    11:38am - 4:50pm
    Mon Mar 24th 2025
    23h 12m
    Chicago (MDW) → Turin (TRN)
    2 Stops

    Mon Mar 24th 2025 Frontier Airlines · F9 1458 Depart at 11:38am from Chicago (MDW) Fly for 2h 41m Arrive at 3:19pm in Orlando (MCO)

    Layover in Orlando for 6h 36m

    Mon Mar 24th 2025 Norse Atlantic UK · Z0 784 Depart at 9:55pm from Orlando (MCO) Fly for 8h 5m Arrive at 10:00am in London (LGW)

    Layover in London for 4h 0m

    Tue Mar 25th 2025 easyJet · U2 8359 Depart at 2:00pm from London (LGW) Fly for 1h 50m Arrive at 4:50pm in Turin (TRN)

  • US$866
    Frontier AirlinesNorse Atlantic UKVueling
    2:54pm - 10:55pm
    Thu Mar 6th 2025
    25h 1m
    Chicago (MDW) → Florence (FLR)
    2 Stops

    Thu Mar 6th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 2h 10m

    Thu Mar 6th 2025 Norse Atlantic UK · Z0 784 Depart at 8:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 9h 55m

    Fri Mar 7th 2025 Vueling · VY 6209 Depart at 7:55pm from London (LGW) Fly for 2h 0m Arrive at 10:55pm in Florence (FLR)

  • US$871
    Frontier AirlinesNorse Atlantic UKeasyJet
    11:38am - 4:40pm
    Mon Mar 24th 2025
    23h 2m
    Chicago (MDW) → Pisa (PSA)
    2 Stops

    Mon Mar 24th 2025 Frontier Airlines · F9 1458 Depart at 11:38am from Chicago (MDW) Fly for 2h 41m Arrive at 3:19pm in Orlando (MCO)

    Layover in Orlando for 6h 36m

    Mon Mar 24th 2025 Norse Atlantic UK · Z0 784 Depart at 9:55pm from Orlando (MCO) Fly for 8h 5m Arrive at 10:00am in London (LGW)

    Layover in London for 3h 30m

    Tue Mar 25th 2025 easyJet · U2 8317 Depart at 1:30pm from London (LGW) Fly for 2h 10m Arrive at 4:40pm in Pisa (PSA)

  • US$878
    Frontier AirlinesPlayWizz Air Malta
    3:28pm - 1:10am
    Mon Mar 17th 2025
    51h 42m
    Chicago (MDW) → Rome (FCO)
    2 Stops

    Mon Mar 17th 2025 Frontier Airlines · F9 3088 Depart at 3:28pm from Chicago (MDW) Fly for 1h 51m Arrive at 6:19pm in Washington, D.C. (BWI)

    Layover in Washington, D.C. for 24h 46m

    Tue Mar 18th 2025 Play · OG 102 Depart at 7:05pm from Washington, D.C. (BWI) Fly for 6h 0m Arrive at 5:05am in Reykjavik (KEF)

    Layover in Reykjavik for 14h 20m

    Wed Mar 19th 2025 Wizz Air Malta · W4 6098 Depart at 7:25pm from Reykjavik (KEF) Fly for 4h 45m Arrive at 1:10am in Rome (FCO)

  • US$882
    Frontier AirlinesNorse Atlantic UKeasyJet
    11:38am - 5:55pm
    Mon Mar 24th 2025
    24h 17m
    Chicago (MDW) → Milan (MXP)
    2 Stops

    Mon Mar 24th 2025 Frontier Airlines · F9 1458 Depart at 11:38am from Chicago (MDW) Fly for 2h 41m Arrive at 3:19pm in Orlando (MCO)

    Layover in Orlando for 6h 36m

    Mon Mar 24th 2025 Norse Atlantic UK · Z0 784 Depart at 9:55pm from Orlando (MCO) Fly for 8h 5m Arrive at 10:00am in London (LGW)

    Layover in London for 5h 0m

    Tue Mar 25th 2025 easyJet · U2 8309 Depart at 3:00pm from London (LGW) Fly for 1h 55m Arrive at 5:55pm in Milan (MXP)

  • US$882
    Frontier AirlinesNorse Atlantic UKeasyJet
    2:54pm - 3:45pm
    Thu Mar 20th 2025
    18h 51m
    Chicago (MDW) → Milan (MXP)
    2 Stops

    Thu Mar 20th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 3h 10m

    Thu Mar 20th 2025 Norse Atlantic UK · Z0 784 Depart at 9:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 2h 45m

    Fri Mar 21st 2025 easyJet · U2 8377 Depart at 12:45pm from London (LGW) Fly for 2h 0m Arrive at 3:45pm in Milan (MXP)

  • US$882
    Frontier AirlinesNorse Atlantic UKeasyJet
    2:54pm - 5:20pm
    Thu Mar 20th 2025
    20h 26m
    Chicago (MDW) → Verona (VRN)
    2 Stops

    Thu Mar 20th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 3h 10m

    Thu Mar 20th 2025 Norse Atlantic UK · Z0 784 Depart at 9:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 4h 20m

    Fri Mar 21st 2025 easyJet · U2 8335 Depart at 2:20pm from London (LGW) Fly for 2h 0m Arrive at 5:20pm in Verona (VRN)

  • US$882
    Frontier AirlinesNorse Atlantic UKeasyJet
    2:54pm - 8:25pm
    Thu Mar 20th 2025
    23h 31m
    Chicago (MDW) → Milan (MXP)
    2 Stops

    Thu Mar 20th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 3h 10m

    Thu Mar 20th 2025 Norse Atlantic UK · Z0 784 Depart at 9:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 7h 30m

    Fri Mar 21st 2025 easyJet · U2 8311 Depart at 5:30pm from London (LGW) Fly for 1h 55m Arrive at 8:25pm in Milan (MXP)

  • US$883
    Frontier AirlinesNorse Atlantic UKeasyJet
    2:54pm - 8:25pm
    Thu Mar 6th 2025
    22h 31m
    Chicago (MDW) → Milan (MXP)
    2 Stops

    Thu Mar 6th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 2h 10m

    Thu Mar 6th 2025 Norse Atlantic UK · Z0 784 Depart at 8:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 7h 30m

    Fri Mar 7th 2025 easyJet · U2 8311 Depart at 5:30pm from London (LGW) Fly for 1h 55m Arrive at 8:25pm in Milan (MXP)

  • US$883.37
    Frontier AirlinesNorse Atlantic UKRyanairRyanair
    11:38am - 8:25pm
    Mon Mar 24th 2025
    26h 47m
    Chicago (MDW) → Milan (BGY)
    3 Stops

    Mon Mar 24th 2025 Frontier Airlines · F9 1458 Depart at 11:38am from Chicago (MDW) Fly for 2h 41m Arrive at 3:19pm in Orlando (MCO)

    Layover in Orlando for 6h 36m

    Mon Mar 24th 2025 Norse Atlantic UK · Z0 784 Depart at 9:55pm from Orlando (MCO) Fly for 8h 5m Arrive at 10:00am in London (LGW)

    Layover in London for 3h 25m

    Tue Mar 25th 2025 Ryanair · FR 119 Depart at 1:25pm from London (LGW) Fly for 1h 20m Arrive at 2:45pm in Dublin (DUB)

    Layover in Dublin for 2h 15m

    Tue Mar 25th 2025 Ryanair · FR 4844 Depart at 5:00pm from Dublin (DUB) Fly for 2h 25m Arrive at 8:25pm in Milan (BGY)

  • US$888
    Frontier AirlinesNorse Atlantic UKVueling
    2:54pm - 10:55pm
    Thu Mar 20th 2025
    26h 1m
    Chicago (MDW) → Florence (FLR)
    2 Stops

    Thu Mar 20th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 3h 10m

    Thu Mar 20th 2025 Norse Atlantic UK · Z0 784 Depart at 9:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 9h 55m

    Fri Mar 21st 2025 Vueling · VY 6209 Depart at 7:55pm from London (LGW) Fly for 2h 0m Arrive at 10:55pm in Florence (FLR)

  • US$893
    Frontier AirlinesNorse Atlantic UKBritish Airways
    11:38am - 6:15pm
    Mon Mar 24th 2025
    24h 37m
    Chicago (MDW) → Verona (VRN)
    2 Stops

    Mon Mar 24th 2025 Frontier Airlines · F9 1458 Depart at 11:38am from Chicago (MDW) Fly for 2h 41m Arrive at 3:19pm in Orlando (MCO)

    Layover in Orlando for 6h 36m

    Mon Mar 24th 2025 Norse Atlantic UK · Z0 784 Depart at 9:55pm from Orlando (MCO) Fly for 8h 5m Arrive at 10:00am in London (LGW)

    Layover in London for 5h 10m

    Tue Mar 25th 2025 British Airways · BA 2590 Depart at 3:10pm from London (LGW) Fly for 2h 5m Arrive at 6:15pm in Verona (VRN)

  • US$895
    Frontier AirlinesNorse Atlantic UKeasyJet
    2:54pm - 4:40pm
    Thu Mar 6th 2025
    18h 46m
    Chicago (MDW) → Pisa (PSA)
    2 Stops

    Thu Mar 6th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 2h 10m

    Thu Mar 6th 2025 Norse Atlantic UK · Z0 784 Depart at 8:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 3h 30m

    Fri Mar 7th 2025 easyJet · U2 8315 Depart at 1:30pm from London (LGW) Fly for 2h 10m Arrive at 4:40pm in Pisa (PSA)

  • US$898
    Frontier AirlinesNorse Atlantic UKeasyJet
    2:54pm - 6:00pm
    Thu Mar 6th 2025
    20h 6m
    Chicago (MDW) → Milan (MXP)
    2 Stops

    Thu Mar 6th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 2h 10m

    Thu Mar 6th 2025 Norse Atlantic UK · Z0 784 Depart at 8:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 5h 0m

    Fri Mar 7th 2025 easyJet · U2 8309 Depart at 3:00pm from London (LGW) Fly for 2h 0m Arrive at 6:00pm in Milan (MXP)

  • US$899
    Frontier AirlinesNorse Atlantic UKeasyJet
    2:54pm - 6:00pm
    Thu Mar 20th 2025
    21h 6m
    Chicago (MDW) → Milan (MXP)
    2 Stops

    Thu Mar 20th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 3h 10m

    Thu Mar 20th 2025 Norse Atlantic UK · Z0 784 Depart at 9:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 5h 0m

    Fri Mar 21st 2025 easyJet · U2 8309 Depart at 3:00pm from London (LGW) Fly for 2h 0m Arrive at 6:00pm in Milan (MXP)

  • US$901
    Frontier AirlinesNorse Atlantic UKeasyJet
    2:54pm - 3:45pm
    Thu Mar 6th 2025
    17h 51m
    Chicago (MDW) → Milan (MXP)
    2 Stops

    Thu Mar 6th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 2h 10m

    Thu Mar 6th 2025 Norse Atlantic UK · Z0 784 Depart at 8:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 2h 45m

    Fri Mar 7th 2025 easyJet · U2 8377 Depart at 12:45pm from London (LGW) Fly for 2h 0m Arrive at 3:45pm in Milan (MXP)

  • US$904
    Frontier AirlinesNorse Atlantic UKeasyJet
    2:54pm - 7:25pm
    Thu Mar 6th 2025
    21h 31m
    Chicago (MDW) → Venice (VCE)
    2 Stops

    Thu Mar 6th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 2h 10m

    Thu Mar 6th 2025 Norse Atlantic UK · Z0 784 Depart at 8:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 6h 20m

    Fri Mar 7th 2025 easyJet · U2 8295 Depart at 4:20pm from London (LGW) Fly for 2h 5m Arrive at 7:25pm in Venice (VCE)

  • US$904
    Frontier AirlinesNorse Atlantic UKeasyJet
    2:54pm - 7:25pm
    Thu Mar 20th 2025
    22h 31m
    Chicago (MDW) → Venice (VCE)
    2 Stops

    Thu Mar 20th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 3h 10m

    Thu Mar 20th 2025 Norse Atlantic UK · Z0 784 Depart at 9:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 6h 20m

    Fri Mar 21st 2025 easyJet · U2 8295 Depart at 4:20pm from London (LGW) Fly for 2h 5m Arrive at 7:25pm in Venice (VCE)

  • US$904
    Frontier AirlinesNorse Atlantic UKBritish Airways
    2:54pm - 8:40pm
    Thu Mar 6th 2025
    22h 46m
    Chicago (MDW) → Turin (TRN)
    2 Stops

    Thu Mar 6th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 2h 10m

    Thu Mar 6th 2025 Norse Atlantic UK · Z0 784 Depart at 8:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 7h 50m

    Fri Mar 7th 2025 British Airways · BA 2598 Depart at 5:50pm from London (LGW) Fly for 1h 50m Arrive at 8:40pm in Turin (TRN)

  • US$906
    Frontier AirlinesNorse Atlantic UKeasyJet
    2:54pm - 8:05pm
    Thu Mar 6th 2025
    22h 11m
    Chicago (MDW) → Naples (NAP)
    2 Stops

    Thu Mar 6th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 2h 10m

    Thu Mar 6th 2025 Norse Atlantic UK · Z0 784 Depart at 8:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 6h 25m

    Fri Mar 7th 2025 easyJet · U2 8341 Depart at 4:25pm from London (LGW) Fly for 2h 40m Arrive at 8:05pm in Naples (NAP)

  • US$914
    Frontier AirlinesNorse Atlantic UKVueling
    2:54pm - 12:10am
    Thu Mar 6th 2025
    26h 16m
    Chicago (MDW) → Rome (FCO)
    2 Stops

    Thu Mar 6th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 2h 10m

    Thu Mar 6th 2025 Norse Atlantic UK · Z0 784 Depart at 8:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 10h 50m

    Fri Mar 7th 2025 Vueling · VY 6225 Depart at 8:50pm from London (LGW) Fly for 2h 20m Arrive at 12:10am in Rome (FCO)

  • US$916
    Frontier AirlinesNorse Atlantic UKeasyJet
    2:54pm - 8:05pm
    Thu Mar 20th 2025
    23h 11m
    Chicago (MDW) → Naples (NAP)
    2 Stops

    Thu Mar 20th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 3h 10m

    Thu Mar 20th 2025 Norse Atlantic UK · Z0 784 Depart at 9:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 6h 25m

    Fri Mar 21st 2025 easyJet · U2 8341 Depart at 4:25pm from London (LGW) Fly for 2h 40m Arrive at 8:05pm in Naples (NAP)

  • US$920
    Frontier AirlinesNorse Atlantic UKBritish Airways
    2:54pm - 6:15pm
    Thu Mar 6th 2025
    20h 21m
    Chicago (MDW) → Verona (VRN)
    2 Stops

    Thu Mar 6th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 2h 10m

    Thu Mar 6th 2025 Norse Atlantic UK · Z0 784 Depart at 8:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 5h 10m

    Fri Mar 7th 2025 British Airways · BA 2590 Depart at 3:10pm from London (LGW) Fly for 2h 5m Arrive at 6:15pm in Verona (VRN)

  • US$925.74
    Frontier AirlinesNorse Atlantic UKeasyJetRyanair
    2:54pm - 11:15pm
    Thu Mar 6th 2025
    25h 21m
    Chicago (MDW) → Catania (CTA)
    3 Stops

    Thu Mar 6th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 2h 10m

    Thu Mar 6th 2025 Norse Atlantic UK · Z0 784 Depart at 8:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 5h 0m

    Fri Mar 7th 2025 easyJet · U2 8763 Depart at 3:00pm from London (LGW) Fly for 3h 15m Arrive at 7:15pm in Malta (MLA)

    Layover in Malta for 3h 10m

    Fri Mar 7th 2025 Ryanair · FR 367 Depart at 10:25pm from Malta (MLA) Fly for 0h 50m Arrive at 11:15pm in Catania (CTA)

  • US$925.78
    Frontier AirlinesNorse Atlantic UKVuelingRyanair
    2:54pm - 10:45pm
    Thu Mar 20th 2025
    25h 51m
    Chicago (MDW) → Milan (BGY)
    3 Stops

    Thu Mar 20th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 3h 10m

    Thu Mar 20th 2025 Norse Atlantic UK · Z0 784 Depart at 9:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 3h 55m

    Fri Mar 21st 2025 Vueling · VY 7841 Depart at 1:55pm from London (LGW) Fly for 2h 0m Arrive at 4:55pm in Barcelona (BCN)

    Layover in Barcelona for 4h 5m

    Fri Mar 21st 2025 Ryanair · FR 6305 Depart at 9:00pm from Barcelona (BCN) Fly for 1h 45m Arrive at 10:45pm in Milan (BGY)

  • US$932.37
    Frontier AirlinesNorse Atlantic UKVuelingRyanair
    2:54pm - 10:45pm
    Thu Mar 6th 2025
    24h 51m
    Chicago (MDW) → Milan (BGY)
    3 Stops

    Thu Mar 6th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 2h 10m

    Thu Mar 6th 2025 Norse Atlantic UK · Z0 784 Depart at 8:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 3h 55m

    Fri Mar 7th 2025 Vueling · VY 7841 Depart at 1:55pm from London (LGW) Fly for 2h 0m Arrive at 4:55pm in Barcelona (BCN)

    Layover in Barcelona for 4h 5m

    Fri Mar 7th 2025 Ryanair · FR 6305 Depart at 9:00pm from Barcelona (BCN) Fly for 1h 45m Arrive at 10:45pm in Milan (BGY)

  • US$933
    Frontier AirlinesNorse Atlantic UKeasyJet
    2:54pm - 4:40pm
    Thu Mar 20th 2025
    19h 46m
    Chicago (MDW) → Pisa (PSA)
    2 Stops

    Thu Mar 20th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 3h 10m

    Thu Mar 20th 2025 Norse Atlantic UK · Z0 784 Depart at 9:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 3h 30m

    Fri Mar 21st 2025 easyJet · U2 8315 Depart at 1:30pm from London (LGW) Fly for 2h 10m Arrive at 4:40pm in Pisa (PSA)

  • US$934.55
    Frontier AirlinesNorse Atlantic UKVuelingRyanair
    2:54pm - 10:15pm
    Thu Mar 6th 2025
    24h 21m
    Chicago (MDW) → Trieste (TRS)
    3 Stops

    Thu Mar 6th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 2h 10m

    Thu Mar 6th 2025 Norse Atlantic UK · Z0 784 Depart at 8:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 3h 55m

    Fri Mar 7th 2025 Vueling · VY 7841 Depart at 1:55pm from London (LGW) Fly for 2h 0m Arrive at 4:55pm in Barcelona (BCN)

    Layover in Barcelona for 3h 20m

    Fri Mar 7th 2025 Ryanair · FR 3928 Depart at 8:15pm from Barcelona (BCN) Fly for 2h 0m Arrive at 10:15pm in Trieste (TRS)

  • US$938
    Frontier AirlinesNorse Atlantic UKeasyJet
    2:54pm - 3:55pm
    Thu Mar 20th 2025
    19h 1m
    Chicago (MDW) → Rome (FCO)
    2 Stops

    Thu Mar 20th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 3h 10m

    Thu Mar 20th 2025 Norse Atlantic UK · Z0 784 Depart at 9:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 2h 30m

    Fri Mar 21st 2025 easyJet · U2 6506 Depart at 12:30pm from London (LGW) Fly for 2h 25m Arrive at 3:55pm in Rome (FCO)

  • US$939
    Frontier AirlinesNorse Atlantic UKBritish Airways
    2:54pm - 6:15pm
    Thu Mar 20th 2025
    21h 21m
    Chicago (MDW) → Verona (VRN)
    2 Stops

    Thu Mar 20th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 3h 10m

    Thu Mar 20th 2025 Norse Atlantic UK · Z0 784 Depart at 9:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 5h 10m

    Fri Mar 21st 2025 British Airways · BA 2590 Depart at 3:10pm from London (LGW) Fly for 2h 5m Arrive at 6:15pm in Verona (VRN)

  • US$942.47
    Frontier AirlinesNorse Atlantic UKRyanairRyanair
    2:54pm - 8:25pm
    Thu Mar 6th 2025
    22h 31m
    Chicago (MDW) → Milan (BGY)
    3 Stops

    Thu Mar 6th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 2h 10m

    Thu Mar 6th 2025 Norse Atlantic UK · Z0 784 Depart at 8:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 3h 20m

    Fri Mar 7th 2025 Ryanair · FR 117 Depart at 1:20pm from London (LGW) Fly for 1h 20m Arrive at 2:40pm in Dublin (DUB)

    Layover in Dublin for 2h 20m

    Fri Mar 7th 2025 Ryanair · FR 4844 Depart at 5:00pm from Dublin (DUB) Fly for 2h 25m Arrive at 8:25pm in Milan (BGY)

  • US$952.43
    Frontier AirlinesNorse Atlantic UKVuelingRyanair
    2:54pm - 10:15pm
    Thu Mar 20th 2025
    25h 21m
    Chicago (MDW) → Trieste (TRS)
    3 Stops

    Thu Mar 20th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 3h 10m

    Thu Mar 20th 2025 Norse Atlantic UK · Z0 784 Depart at 9:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 3h 55m

    Fri Mar 21st 2025 Vueling · VY 7841 Depart at 1:55pm from London (LGW) Fly for 2h 0m Arrive at 4:55pm in Barcelona (BCN)

    Layover in Barcelona for 3h 20m

    Fri Mar 21st 2025 Ryanair · FR 3928 Depart at 8:15pm from Barcelona (BCN) Fly for 2h 0m Arrive at 10:15pm in Trieste (TRS)

  • US$961
    Frontier AirlinesNorse Atlantic UKeasyJetKM Malta Airlines
    2:54pm - 9:45pm
    Thu Mar 6th 2025
    23h 51m
    Chicago (MDW) → Catania (CTA)
    3 Stops

    Thu Mar 6th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 2h 10m

    Thu Mar 6th 2025 Norse Atlantic UK · Z0 784 Depart at 8:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 5h 0m

    Fri Mar 7th 2025 easyJet · U2 8763 Depart at 3:00pm from London (LGW) Fly for 3h 15m Arrive at 7:15pm in Malta (MLA)

    Layover in Malta for 1h 45m

    Fri Mar 7th 2025 KM Malta Airlines · KM 642 Depart at 9:00pm from Malta (MLA) Fly for 0h 45m Arrive at 9:45pm in Catania (CTA)

  • US$963.67
    Frontier AirlinesNorse Atlantic UKAegeanRyanair
    2:54pm - 9:05pm
    Thu Mar 20th 2025
    24h 11m
    Chicago (MDW) → Milan (BGY)
    3 Stops

    Thu Mar 20th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 3h 10m

    Thu Mar 20th 2025 Norse Atlantic UK · Z0 784 Depart at 9:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 2h 15m

    Fri Mar 21st 2025 Aegean · A3 607 Depart at 12:15pm from London (LGW) Fly for 3h 35m Arrive at 5:50pm in Athens (ATH)

    Layover in Athens for 1h 40m

    Fri Mar 21st 2025 Ryanair · FR 2090 Depart at 7:30pm from Athens (ATH) Fly for 2h 35m Arrive at 9:05pm in Milan (BGY)

  • US$965
    Frontier AirlinesNorse Atlantic UKVuelingeasyJet
    2:54pm - 7:25pm
    Thu Mar 20th 2025
    22h 31m
    Chicago (MDW) → Milan (LIN)
    3 Stops

    Thu Mar 20th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 3h 10m

    Thu Mar 20th 2025 Norse Atlantic UK · Z0 784 Depart at 9:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 3h 25m

    Fri Mar 21st 2025 Vueling · VY 6947 Depart at 1:25pm from London (LGW) Fly for 1h 20m Arrive at 3:45pm in Paris (ORY)

    Layover in Paris for 2h 15m

    Fri Mar 21st 2025 easyJet · U2 4831 Depart at 6:00pm from Paris (ORY) Fly for 1h 25m Arrive at 7:25pm in Milan (LIN)

  • US$967.14
    Frontier AirlinesNorse Atlantic UKBritish AirwaysRyanair
    2:54pm - 9:00pm
    Thu Mar 20th 2025
    24h 6m
    Chicago (MDW) → Trapani (TPS)
    3 Stops

    Thu Mar 20th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 3h 10m

    Thu Mar 20th 2025 Norse Atlantic UK · Z0 784 Depart at 9:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 3h 45m

    Fri Mar 21st 2025 British Airways · BA 2616 Depart at 1:45pm from London (LGW) Fly for 3h 10m Arrive at 5:55pm in Malta (MLA)

    Layover in Malta for 2h 10m

    Fri Mar 21st 2025 Ryanair · FR 7005 Depart at 8:05pm from Malta (MLA) Fly for 0h 55m Arrive at 9:00pm in Trapani (TPS)

  • US$968.14
    Frontier AirlinesNorse Atlantic UKBritish AirwaysRyanair
    2:54pm - 9:00pm
    Thu Mar 6th 2025
    23h 6m
    Chicago (MDW) → Trapani (TPS)
    3 Stops

    Thu Mar 6th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 2h 10m

    Thu Mar 6th 2025 Norse Atlantic UK · Z0 784 Depart at 8:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 3h 45m

    Fri Mar 7th 2025 British Airways · BA 2616 Depart at 1:45pm from London (LGW) Fly for 3h 10m Arrive at 5:55pm in Malta (MLA)

    Layover in Malta for 2h 10m

    Fri Mar 7th 2025 Ryanair · FR 7005 Depart at 8:05pm from Malta (MLA) Fly for 0h 55m Arrive at 9:00pm in Trapani (TPS)

  • US$971.74
    Frontier AirlinesNorse Atlantic UKWizz AirRyanair
    2:54pm - 8:30pm
    Thu Mar 6th 2025
    22h 36m
    Chicago (MDW) → Catania (CTA)
    3 Stops

    Thu Mar 6th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 2h 10m

    Thu Mar 6th 2025 Norse Atlantic UK · Z0 784 Depart at 8:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 3h 20m

    Fri Mar 7th 2025 Wizz Air · W6 2222 Depart at 1:20pm from London (LGW) Fly for 2h 25m Arrive at 4:45pm in Budapest (BUD)

    Layover in Budapest for 1h 40m

    Fri Mar 7th 2025 Ryanair · FR 6288 Depart at 6:25pm from Budapest (BUD) Fly for 2h 5m Arrive at 8:30pm in Catania (CTA)

  • US$974.68
    Frontier AirlinesNorse Atlantic UKBritish AirwaysRyanair
    2:54pm - 10:25pm
    Thu Mar 6th 2025
    24h 31m
    Chicago (MDW) → Bologna (BLQ)
    3 Stops

    Thu Mar 6th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 2h 10m

    Thu Mar 6th 2025 Norse Atlantic UK · Z0 784 Depart at 8:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 3h 45m

    Fri Mar 7th 2025 British Airways · BA 2616 Depart at 1:45pm from London (LGW) Fly for 3h 10m Arrive at 5:55pm in Malta (MLA)

    Layover in Malta for 2h 35m

    Fri Mar 7th 2025 Ryanair · FR 3779 Depart at 8:30pm from Malta (MLA) Fly for 1h 55m Arrive at 10:25pm in Bologna (BLQ)

  • US$983
    Frontier AirlinesNorse Atlantic UKVueling
    11:38am - 6:00pm
    Mon Mar 10th 2025
    24h 22m
    Chicago (MDW) → Florence (FLR)
    2 Stops

    Mon Mar 10th 2025 Frontier Airlines · F9 1458 Depart at 11:38am from Chicago (MDW) Fly for 2h 41m Arrive at 3:19pm in Orlando (MCO)

    Layover in Orlando for 6h 36m

    Mon Mar 10th 2025 Norse Atlantic UK · Z0 784 Depart at 9:55pm from Orlando (MCO) Fly for 8h 5m Arrive at 10:00am in London (LGW)

    Layover in London for 4h 55m

    Tue Mar 11th 2025 Vueling · VY 6207 Depart at 2:55pm from London (LGW) Fly for 2h 5m Arrive at 6:00pm in Florence (FLR)

  • US$1001.47
    Frontier AirlinesNorse Atlantic UKeasyJetRyanair
    2:54pm - 8:35pm
    Thu Mar 20th 2025
    23h 41m
    Chicago (MDW) → Venice (TSF)
    3 Stops

    Thu Mar 20th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 3h 10m

    Thu Mar 20th 2025 Norse Atlantic UK · Z0 784 Depart at 9:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 2h 40m

    Fri Mar 21st 2025 easyJet · U2 8011 Depart at 12:40pm from London (LGW) Fly for 2h 25m Arrive at 4:05pm in Valencia (VLC)

    Layover in Valencia for 2h 20m

    Fri Mar 21st 2025 Ryanair · FR 7266 Depart at 6:25pm from Valencia (VLC) Fly for 2h 10m Arrive at 8:35pm in Venice (TSF)

  • US$1016
    Frontier AirlinesNorse Atlantic UKVueling
    2:54pm - 6:00pm
    Thu Mar 6th 2025
    20h 6m
    Chicago (MDW) → Florence (FLR)
    2 Stops

    Thu Mar 6th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 2h 10m

    Thu Mar 6th 2025 Norse Atlantic UK · Z0 784 Depart at 8:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 4h 55m

    Fri Mar 7th 2025 Vueling · VY 6207 Depart at 2:55pm from London (LGW) Fly for 2h 5m Arrive at 6:00pm in Florence (FLR)

  • US$1025
    Frontier AirlinesNorse Atlantic UKeasyJet
    11:38am - 4:50pm
    Mon Mar 10th 2025
    23h 12m
    Chicago (MDW) → Turin (TRN)
    2 Stops

    Mon Mar 10th 2025 Frontier Airlines · F9 1458 Depart at 11:38am from Chicago (MDW) Fly for 2h 41m Arrive at 3:19pm in Orlando (MCO)

    Layover in Orlando for 6h 36m

    Mon Mar 10th 2025 Norse Atlantic UK · Z0 784 Depart at 9:55pm from Orlando (MCO) Fly for 8h 5m Arrive at 10:00am in London (LGW)

    Layover in London for 4h 0m

    Tue Mar 11th 2025 easyJet · U2 8359 Depart at 2:00pm from London (LGW) Fly for 1h 50m Arrive at 4:50pm in Turin (TRN)

  • US$1026
    Frontier AirlinesNorse Atlantic UKBritish AirwayseasyJet
    2:54pm - 7:05pm
    Thu Mar 6th 2025
    21h 11m
    Chicago (MDW) → Naples (NAP)
    3 Stops

    Thu Mar 6th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 2h 10m

    Thu Mar 6th 2025 Norse Atlantic UK · Z0 784 Depart at 8:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 2h 35m

    Fri Mar 7th 2025 British Airways · BA 2560 Depart at 12:35pm from London (LGW) Fly for 1h 40m Arrive at 3:15pm in Geneva (GVA)

    Layover in Geneva for 2h 5m

    Fri Mar 7th 2025 easyJet · U2 4226 Depart at 5:20pm from Geneva (GVA) Fly for 1h 45m Arrive at 7:05pm in Naples (NAP)

  • US$1033
    Frontier AirlinesNorse Atlantic UKeasyJet
    10:08am - 4:15pm
    Sat Mar 8th 2025
    23h 7m
    Chicago (MDW) → Rome (FCO)
    2 Stops

    Sat Mar 8th 2025 Frontier Airlines · F9 1458 Depart at 10:08am from Chicago (MDW) Fly for 2h 41m Arrive at 1:49pm in Orlando (MCO)

    Layover in Orlando for 6h 56m

    Sat Mar 8th 2025 Norse Atlantic UK · Z0 784 Depart at 8:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 2h 50m

    Sun Mar 9th 2025 easyJet · U2 8325 Depart at 12:50pm from London (LGW) Fly for 2h 25m Arrive at 4:15pm in Rome (FCO)

  • US$1034.10
    Frontier AirlinesNorse Atlantic UKeasyJetRyanair
    2:54pm - 8:35pm
    Thu Mar 6th 2025
    22h 41m
    Chicago (MDW) → Venice (TSF)
    3 Stops

    Thu Mar 6th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 2h 10m

    Thu Mar 6th 2025 Norse Atlantic UK · Z0 784 Depart at 8:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 2h 40m

    Fri Mar 7th 2025 easyJet · U2 8011 Depart at 12:40pm from London (LGW) Fly for 2h 25m Arrive at 4:05pm in Valencia (VLC)

    Layover in Valencia for 2h 20m

    Fri Mar 7th 2025 Ryanair · FR 7266 Depart at 6:25pm from Valencia (VLC) Fly for 2h 10m Arrive at 8:35pm in Venice (TSF)

  • US$1037
    Frontier AirlinesNorse Atlantic UKeasyJeteasyJet
    2:54pm - 7:05pm
    Thu Mar 6th 2025
    21h 11m
    Chicago (MDW) → Naples (NAP)
    3 Stops

    Thu Mar 6th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 2h 10m

    Thu Mar 6th 2025 Norse Atlantic UK · Z0 784 Depart at 8:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 2h 45m

    Fri Mar 7th 2025 easyJet · U2 8489 Depart at 12:45pm from London (LGW) Fly for 1h 35m Arrive at 3:20pm in Geneva (GVA)

    Layover in Geneva for 2h 0m

    Fri Mar 7th 2025 easyJet · U2 4226 Depart at 5:20pm from Geneva (GVA) Fly for 1h 45m Arrive at 7:05pm in Naples (NAP)

  • US$1044
    Frontier AirlinesNorse Atlantic UKeasyJet
    10:08am - 4:15pm
    Sat Mar 8th 2025
    23h 7m
    Chicago (MDW) → Verona (VRN)
    2 Stops

    Sat Mar 8th 2025 Frontier Airlines · F9 1458 Depart at 10:08am from Chicago (MDW) Fly for 2h 41m Arrive at 1:49pm in Orlando (MCO)

    Layover in Orlando for 6h 56m

    Sat Mar 8th 2025 Norse Atlantic UK · Z0 784 Depart at 8:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 3h 15m

    Sun Mar 9th 2025 easyJet · U2 8335 Depart at 1:15pm from London (LGW) Fly for 2h 0m Arrive at 4:15pm in Verona (VRN)

  • US$1047
    Frontier AirlinesNorse Atlantic UKBritish AirwayseasyJet
    2:54pm - 7:05pm
    Thu Mar 20th 2025
    22h 11m
    Chicago (MDW) → Naples (NAP)
    3 Stops

    Thu Mar 20th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 3h 10m

    Thu Mar 20th 2025 Norse Atlantic UK · Z0 784 Depart at 9:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 2h 35m

    Fri Mar 21st 2025 British Airways · BA 2560 Depart at 12:35pm from London (LGW) Fly for 1h 40m Arrive at 3:15pm in Geneva (GVA)

    Layover in Geneva for 2h 5m

    Fri Mar 21st 2025 easyJet · U2 4226 Depart at 5:20pm from Geneva (GVA) Fly for 1h 45m Arrive at 7:05pm in Naples (NAP)

  • US$1053
    Frontier AirlinesNorse Atlantic UKeasyJeteasyJet
    2:54pm - 7:15pm
    Thu Mar 6th 2025
    21h 21m
    Chicago (MDW) → Venice (VCE)
    3 Stops

    Thu Mar 6th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 2h 10m

    Thu Mar 6th 2025 Norse Atlantic UK · Z0 784 Depart at 8:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 2h 50m

    Fri Mar 7th 2025 easyJet · U2 8419 Depart at 12:50pm from London (LGW) Fly for 2h 0m Arrive at 3:50pm in Nice (NCE)

    Layover in Nice for 2h 20m

    Fri Mar 7th 2025 easyJet · U2 4004 Depart at 6:10pm from Nice (NCE) Fly for 1h 5m Arrive at 7:15pm in Venice (VCE)

  • US$1055
    Frontier AirlinesNorse Atlantic UKVueling
    2:54pm - 6:00pm
    Thu Mar 20th 2025
    21h 6m
    Chicago (MDW) → Florence (FLR)
    2 Stops

    Thu Mar 20th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 3h 10m

    Thu Mar 20th 2025 Norse Atlantic UK · Z0 784 Depart at 9:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 4h 55m

    Fri Mar 21st 2025 Vueling · VY 6207 Depart at 2:55pm from London (LGW) Fly for 2h 5m Arrive at 6:00pm in Florence (FLR)

  • US$1058.71
    Air FranceAir FranceAir FranceRyanair
    5:59pm - 9:15pm
    Thu Mar 6th 2025
    20h 16m
    Chicago (MDW) → Venice (VCE)
    3 Stops

    Thu Mar 6th 2025 Air France · AF 2651 Depart at 5:59pm from Chicago (MDW) Fly for 1h 15m Arrive at 8:14pm in Detroit (DTW)

    Layover in Detroit for 0h 56m

    Thu Mar 6th 2025 Air France · AF 377 Depart at 9:10pm from Detroit (DTW) Fly for 7h 45m Arrive at 10:55am in Paris (CDG)

    Layover in Paris for 1h 20m

    Fri Mar 7th 2025 Air France · AF 1648 Depart at 12:15pm from Paris (CDG) Fly for 1h 45m Arrive at 2:00pm in Barcelona (BCN)

    Layover in Barcelona for 5h 20m

    Fri Mar 7th 2025 Ryanair · FR 878 Depart at 7:20pm from Barcelona (BCN) Fly for 1h 55m Arrive at 9:15pm in Venice (VCE)

  • US$1062
    Frontier AirlinesNorse Atlantic UKVuelingeasyJet
    2:54pm - 7:25pm
    Thu Mar 6th 2025
    21h 31m
    Chicago (MDW) → Milan (LIN)
    3 Stops

    Thu Mar 6th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 2h 10m

    Thu Mar 6th 2025 Norse Atlantic UK · Z0 784 Depart at 8:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 3h 25m

    Fri Mar 7th 2025 Vueling · VY 6947 Depart at 1:25pm from London (LGW) Fly for 1h 20m Arrive at 3:45pm in Paris (ORY)

    Layover in Paris for 2h 15m

    Fri Mar 7th 2025 easyJet · U2 4831 Depart at 6:00pm from Paris (ORY) Fly for 1h 25m Arrive at 7:25pm in Milan (LIN)

  • US$1069.61
    Air FranceAir FranceAir FranceRyanair
    5:59pm - 10:45pm
    Thu Mar 6th 2025
    21h 46m
    Chicago (MDW) → Milan (BGY)
    3 Stops

    Thu Mar 6th 2025 Air France · AF 2651 Depart at 5:59pm from Chicago (MDW) Fly for 1h 15m Arrive at 8:14pm in Detroit (DTW)

    Layover in Detroit for 0h 56m

    Thu Mar 6th 2025 Air France · AF 377 Depart at 9:10pm from Detroit (DTW) Fly for 7h 45m Arrive at 10:55am in Paris (CDG)

    Layover in Paris for 1h 20m

    Fri Mar 7th 2025 Air France · AF 1648 Depart at 12:15pm from Paris (CDG) Fly for 1h 45m Arrive at 2:00pm in Barcelona (BCN)

    Layover in Barcelona for 7h 0m

    Fri Mar 7th 2025 Ryanair · FR 6305 Depart at 9:00pm from Barcelona (BCN) Fly for 1h 45m Arrive at 10:45pm in Milan (BGY)

  • US$1071
    Frontier AirlinesNorse Atlantic UKeasyJeteasyJet
    2:54pm - 7:15pm
    Thu Mar 20th 2025
    22h 21m
    Chicago (MDW) → Venice (VCE)
    3 Stops

    Thu Mar 20th 2025 Frontier Airlines · F9 1458 Depart at 2:54pm from Chicago (MDW) Fly for 2h 41m Arrive at 6:35pm in Orlando (MCO)

    Layover in Orlando for 3h 10m

    Thu Mar 20th 2025 Norse Atlantic UK · Z0 784 Depart at 9:45pm from Orlando (MCO) Fly for 8h 15m Arrive at 10:00am in London (LGW)

    Layover in London for 2h 50m

    Fri Mar 21st 2025 easyJet · U2 8419 Depart at 12:50pm from London (LGW) Fly for 2h 0m Arrive at 3:50pm in Nice (NCE)

    Layover in Nice for 2h 20m

    Fri Mar 21st 2025 easyJet · U2 4004 Depart at 6:10pm from Nice (NCE) Fly for 1h 5m Arrive at 7:15pm in Venice (VCE)

  • US$1071.79
    Air FranceAir FranceAir FranceRyanair
    5:59pm - 7:00pm
    Thu Mar 6th 2025
    18h 1m
    Chicago (MDW) → Bologna (BLQ)
    3 Stops

    Thu Mar 6th 2025 Air France · AF 2651 Depart at 5:59pm from Chicago (MDW) Fly for 1h 15m Arrive at 8:14pm in Detroit (DTW)

    Layover in Detroit for 0h 56m

    Thu Mar 6th 2025 Air France · AF 377 Depart at 9:10pm from Detroit (DTW) Fly for 7h 45m Arrive at 10:55am in Paris (CDG)

    Layover in Paris for 1h 20m

    Fri Mar 7th 2025 Air France · AF 1648 Depart at 12:15pm from Paris (CDG) Fly for 1h 45m Arrive at 2:00pm in Barcelona (BCN)

    Layover in Barcelona for 3h 15m

    Fri Mar 7th 2025 Ryanair · FR 9366 Depart at 5:15pm from Barcelona (BCN) Fly for 1h 45m Arrive at 7:00pm in Bologna (BLQ)

  • US$1071.79
    Air FranceAir FranceAir FranceRyanair
    5:59pm - 10:15pm
    Thu Mar 6th 2025
    21h 16m
    Chicago (MDW) → Trieste (TRS)
    3 Stops

    Thu Mar 6th 2025 Air France · AF 2651 Depart at 5:59pm from Chicago (MDW) Fly for 1h 15m Arrive at 8:14pm in Detroit (DTW)

    Layover in Detroit for 0h 56m

    Thu Mar 6th 2025 Air France · AF 377 Depart at 9:10pm from Detroit (DTW) Fly for 7h 45m Arrive at 10:55am in Paris (CDG)

    Layover in Paris for 1h 20m

    Fri Mar 7th 2025 Air France · AF 1648 Depart at 12:15pm from Paris (CDG) Fly for 1h 45m Arrive at 2:00pm in Barcelona (BCN)

    Layover in Barcelona for 6h 15m

    Fri Mar 7th 2025 Ryanair · FR 3928 Depart at 8:15pm from Barcelona (BCN) Fly for 2h 0m Arrive at 10:15pm in Trieste (TRS)

  • US$1103.73
    Air FranceAir FranceAir FranceRyanair
    5:59pm - 9:25pm
    Thu Mar 6th 2025
    20h 26m
    Chicago (MDW) → Naples (NAP)
    3 Stops

    Thu Mar 6th 2025 Air France · AF 2651 Depart at 5:59pm from Chicago (MDW) Fly for 1h 15m Arrive at 8:14pm in Detroit (DTW)

    Layover in Detroit for 0h 56m

    Thu Mar 6th 2025 Air France · AF 377 Depart at 9:10pm from Detroit (DTW) Fly for 7h 45m Arrive at 10:55am in Paris (CDG)

    Layover in Paris for 1h 20m

    Fri Mar 7th 2025 Air France · AF 1648 Depart at 12:15pm from Paris (CDG) Fly for 1h 45m Arrive at 2:00pm in Barcelona (BCN)

    Layover in Barcelona for 5h 25m

    Fri Mar 7th 2025 Ryanair · FR 5710 Depart at 7:25pm from Barcelona (BCN) Fly for 2h 0m Arrive at 9:25pm in Naples (NAP)

  • US$1147
    Air FranceAir FranceAir FranceVueling
    5:59pm - 6:05pm
    Thu Mar 6th 2025
    17h 6m
    Chicago (MDW) → Rome (FCO)
    3 Stops

    Thu Mar 6th 2025 Air France · AF 2651 Depart at 5:59pm from Chicago (MDW) Fly for 1h 15m Arrive at 8:14pm in Detroit (DTW)

    Layover in Detroit for 0h 56m

    Thu Mar 6th 2025 Air France · AF 377 Depart at 9:10pm from Detroit (DTW) Fly for 7h 45m Arrive at 10:55am in Paris (CDG)

    Layover in Paris for 1h 20m

    Fri Mar 7th 2025 Air France · AF 1648 Depart at 12:15pm from Paris (CDG) Fly for 1h 45m Arrive at 2:00pm in Barcelona (BCN)

    Layover in Barcelona for 2h 20m

    Fri Mar 7th 2025 Vueling · VY 6108 Depart at 4:20pm from Barcelona (BCN) Fly for 1h 45m Arrive at 6:05pm in Rome (FCO)

  • US$1148.55
    Air FranceAir FranceAir FranceRyanair
    5:59pm - 6:15pm
    Sat Mar 8th 2025
    17h 16m
    Chicago (MDW) → Rome (FCO)
    3 Stops

    Sat Mar 8th 2025 Air France · AF 2651 Depart at 5:59pm from Chicago (MDW) Fly for 1h 15m Arrive at 8:14pm in Detroit (DTW)

    Layover in Detroit for 0h 56m

    Sat Mar 8th 2025 Air France · AF 377 Depart at 9:10pm from Detroit (DTW) Fly for 7h 45m Arrive at 10:55am in Paris (CDG)

    Layover in Paris for 1h 20m

    Sun Mar 9th 2025 Air France · AF 1648 Depart at 12:15pm from Paris (CDG) Fly for 1h 45m Arrive at 2:00pm in Barcelona (BCN)

    Layover in Barcelona for 2h 25m

    Sun Mar 9th 2025 Ryanair · FR 6341 Depart at 4:25pm from Barcelona (BCN) Fly for 1h 50m Arrive at 6:15pm in Rome (FCO)

  • US$1177
    Air FranceAir FranceAir FranceWizz Air Malta
    5:59pm - 6:15pm
    Thu Mar 6th 2025
    17h 16m
    Chicago (MDW) → Milan (MXP)
    3 Stops

    Thu Mar 6th 2025 Air France · AF 2651 Depart at 5:59pm from Chicago (MDW) Fly for 1h 15m Arrive at 8:14pm in Detroit (DTW)

    Layover in Detroit for 0h 56m

    Thu Mar 6th 2025 Air France · AF 377 Depart at 9:10pm from Detroit (DTW) Fly for 7h 45m Arrive at 10:55am in Paris (CDG)

    Layover in Paris for 1h 20m

    Fri Mar 7th 2025 Air France · AF 1648 Depart at 12:15pm from Paris (CDG) Fly for 1h 45m Arrive at 2:00pm in Barcelona (BCN)

    Layover in Barcelona for 2h 30m

    Fri Mar 7th 2025 Wizz Air Malta · W4 6330 Depart at 4:30pm from Barcelona (BCN) Fly for 1h 45m Arrive at 6:15pm in Milan (MXP)

  • US$1277
    Air FranceAir FranceAir France
    1:00pm - 7:45pm
    Wed Mar 5th 2025
    23h 45m
    Chicago (MDW) → Rome (FCO)
    2 Stops

    Wed Mar 5th 2025 Air France · AF 2858 Depart at 1:00pm from Chicago (MDW) Fly for 1h 12m Arrive at 3:12pm in Detroit (DTW)

    Layover in Detroit for 5h 58m

    Wed Mar 5th 2025 Air France · AF 377 Depart at 9:10pm from Detroit (DTW) Fly for 7h 45m Arrive at 10:55am in Paris (CDG)

    Layover in Paris for 6h 45m

    Thu Mar 6th 2025 Air France · AF 1404 Depart at 5:40pm from Paris (CDG) Fly for 2h 5m Arrive at 7:45pm in Rome (FCO)

  • US$1373
    Air FranceAir FranceAir France
    5:59pm - 5:25pm
    Mon Mar 10th 2025
    17h 26m
    Chicago (MDW) → Venice (VCE)
    2 Stops

    Mon Mar 10th 2025 Air France · AF 2651 Depart at 5:59pm from Chicago (MDW) Fly for 1h 15m Arrive at 8:14pm in Detroit (DTW)

    Layover in Detroit for 1h 56m

    Mon Mar 10th 2025 Air France · AF 377 Depart at 10:10pm from Detroit (DTW) Fly for 7h 45m Arrive at 10:55am in Paris (CDG)

    Layover in Paris for 4h 55m

    Tue Mar 11th 2025 Air France · AF 1226 Depart at 3:50pm from Paris (CDG) Fly for 1h 35m Arrive at 5:25pm in Venice (VCE)

  • US$1373
    Air FranceAir FranceAir France
    5:59pm - 6:05pm
    Mon Mar 10th 2025
    18h 6m
    Chicago (MDW) → Turin (TRN)
    2 Stops

    Mon Mar 10th 2025 Air France · AF 2651 Depart at 5:59pm from Chicago (MDW) Fly for 1h 15m Arrive at 8:14pm in Detroit (DTW)

    Layover in Detroit for 1h 56m

    Mon Mar 10th 2025 Air France · AF 377 Depart at 10:10pm from Detroit (DTW) Fly for 7h 45m Arrive at 10:55am in Paris (CDG)

    Layover in Paris for 5h 45m

    Tue Mar 11th 2025 Air France · AF 1202 Depart at 4:40pm from Paris (CDG) Fly for 1h 25m Arrive at 6:05pm in Turin (TRN)

  • US$1379
    Air FranceAir FranceAir France
    5:59pm - 3:50pm
    Thu Mar 6th 2025
    14h 51m
    Chicago (MDW) → Rome (FCO)
    2 Stops

    Thu Mar 6th 2025 Air France · AF 2651 Depart at 5:59pm from Chicago (MDW) Fly for 1h 15m Arrive at 8:14pm in Detroit (DTW)

    Layover in Detroit for 0h 56m

    Thu Mar 6th 2025 Air France · AF 377 Depart at 9:10pm from Detroit (DTW) Fly for 7h 45m Arrive at 10:55am in Paris (CDG)

    Layover in Paris for 2h 50m

    Fri Mar 7th 2025 Air France · AF 1504 Depart at 1:45pm from Paris (CDG) Fly for 2h 5m Arrive at 3:50pm in Rome (FCO)

  • US$1394
    Air FranceAir FranceAir France
    5:59pm - 5:25pm
    Mon Mar 10th 2025
    17h 26m
    Chicago (MDW) → Rome (FCO)
    2 Stops

    Mon Mar 10th 2025 Air France · AF 2651 Depart at 5:59pm from Chicago (MDW) Fly for 1h 15m Arrive at 8:14pm in Detroit (DTW)

    Layover in Detroit for 1h 56m

    Mon Mar 10th 2025 Air France · AF 377 Depart at 10:10pm from Detroit (DTW) Fly for 7h 45m Arrive at 10:55am in Paris (CDG)

    Layover in Paris for 4h 25m

    Tue Mar 11th 2025 Air France · AF 1304 Depart at 3:20pm from Paris (CDG) Fly for 2h 5m Arrive at 5:25pm in Rome (FCO)

  • US$1401
    Air FranceAir FranceAir France
    5:59pm - 5:40pm
    Mon Mar 10th 2025
    17h 41m
    Chicago (MDW) → Milan (MXP)
    2 Stops

    Mon Mar 10th 2025 Air France · AF 2651 Depart at 5:59pm from Chicago (MDW) Fly for 1h 15m Arrive at 8:14pm in Detroit (DTW)

    Layover in Detroit for 1h 56m

    Mon Mar 10th 2025 Air France · AF 377 Depart at 10:10pm from Detroit (DTW) Fly for 7h 45m Arrive at 10:55am in Paris (CDG)

    Layover in Paris for 5h 20m

    Tue Mar 11th 2025 Air France · AF 1730 Depart at 4:15pm from Paris (CDG) Fly for 1h 25m Arrive at 5:40pm in Milan (MXP)

  • US$1401
    Air FranceAir FranceAir France
    5:59pm - 7:35pm
    Mon Mar 10th 2025
    19h 36m
    Chicago (MDW) → Milan (LIN)
    2 Stops

    Mon Mar 10th 2025 Air France · AF 2651 Depart at 5:59pm from Chicago (MDW) Fly for 1h 15m Arrive at 8:14pm in Detroit (DTW)

    Layover in Detroit for 1h 56m

    Mon Mar 10th 2025 Air France · AF 377 Depart at 10:10pm from Detroit (DTW) Fly for 7h 45m Arrive at 10:55am in Paris (CDG)

    Layover in Paris for 7h 15m

    Tue Mar 11th 2025 Air France · AF 1312 Depart at 6:10pm from Paris (CDG) Fly for 1h 25m Arrive at 7:35pm in Milan (LIN)

  • US$1447
    Air FranceAir FranceAir France
    5:59pm - 5:25pm
    Sat Mar 8th 2025
    16h 26m
    Chicago (MDW) → Rome (FCO)
    2 Stops

    Sat Mar 8th 2025 Air France · AF 2651 Depart at 5:59pm from Chicago (MDW) Fly for 1h 15m Arrive at 8:14pm in Detroit (DTW)

    Layover in Detroit for 0h 56m

    Sat Mar 8th 2025 Air France · AF 377 Depart at 9:10pm from Detroit (DTW) Fly for 7h 45m Arrive at 10:55am in Paris (CDG)

    Layover in Paris for 4h 25m

    Sun Mar 9th 2025 Air France · AF 1304 Depart at 3:20pm from Paris (CDG) Fly for 2h 5m Arrive at 5:25pm in Rome (FCO)

  • US$1480
    Air FranceAir FranceAir France
    5:59pm - 5:40pm
    Tue Mar 11th 2025
    17h 41m
    Chicago (MDW) → Milan (MXP)
    2 Stops

    Tue Mar 11th 2025 Air France · AF 2651 Depart at 5:59pm from Chicago (MDW) Fly for 1h 15m Arrive at 8:14pm in Detroit (DTW)

    Layover in Detroit for 1h 56m

    Tue Mar 11th 2025 Air France · AF 377 Depart at 10:10pm from Detroit (DTW) Fly for 7h 45m Arrive at 10:55am in Paris (CDG)

    Layover in Paris for 5h 20m

    Wed Mar 12th 2025 Air France · AF 1730 Depart at 4:15pm from Paris (CDG) Fly for 1h 25m Arrive at 5:40pm in Milan (MXP)

  • US$1585
    Air FranceAir FranceAir France
    5:59pm - 3:50pm
    Sat Mar 8th 2025
    14h 51m
    Chicago (MDW) → Rome (FCO)
    2 Stops

    Sat Mar 8th 2025 Air France · AF 2651 Depart at 5:59pm from Chicago (MDW) Fly for 1h 15m Arrive at 8:14pm in Detroit (DTW)

    Layover in Detroit for 0h 56m

    Sat Mar 8th 2025 Air France · AF 377 Depart at 9:10pm from Detroit (DTW) Fly for 7h 45m Arrive at 10:55am in Paris (CDG)

    Layover in Paris for 2h 50m

    Sun Mar 9th 2025 Air France · AF 1504 Depart at 1:45pm from Paris (CDG) Fly for 2h 5m Arrive at 3:50pm in Rome (FCO)

  • US$2245
    Air FranceAir FranceAir France
    5:59pm - 2:35pm
    Wed Mar 19th 2025
    14h 36m
    Chicago (MDW) → Florence (FLR)
    2 Stops

    Wed Mar 19th 2025 Air France · AF 2651 Depart at 5:59pm from Chicago (MDW) Fly for 1h 15m Arrive at 8:14pm in Detroit (DTW)

    Layover in Detroit for 1h 56m

    Wed Mar 19th 2025 Air France · AF 377 Depart at 10:10pm from Detroit (DTW) Fly for 7h 45m Arrive at 10:55am in Paris (CDG)

    Layover in Paris for 1h 55m

    Thu Mar 20th 2025 Air France · AF 1566 Depart at 12:50pm from Paris (CDG) Fly for 1h 45m Arrive at 2:35pm in Florence (FLR)

  • US$2348
    Air TransatAir CanadaAir Canada
    12:30pm - 9:20am
    Sat Mar 15th 2025
    14h 50m
    Chicago (MDW) → Milan (MXP)
    2 Stops

    Sat Mar 15th 2025 Air Transat · TS 7058 Depart at 12:30pm from Chicago (MDW) Fly for 1h 42m Arrive at 3:12pm in Toronto (YTZ)

    Layover in Toronto for 2h 13m

    Sat Mar 15th 2025 Air Canada · AC 7972 Depart at 5:25pm from Toronto (YTZ) Fly for 1h 15m Arrive at 6:40pm in Montreal (YUL)

    Layover in Montreal for 1h 45m

    Sat Mar 15th 2025 Air Canada · AC 894 Depart at 8:25pm from Montreal (YUL) Fly for 7h 55m Arrive at 9:20am in Milan (MXP)

  • US$2353
    Air TransatAir CanadaAir Canada
    12:30pm - 9:00am
    Sun Mar 9th 2025
    14h 30m
    Chicago (MDW) → Rome (FCO)
    2 Stops

    Sun Mar 9th 2025 Air Transat · TS 7058 Depart at 12:30pm from Chicago (MDW) Fly for 1h 42m Arrive at 3:12pm in Toronto (YTZ)

    Layover in Toronto for 2h 13m

    Sun Mar 9th 2025 Air Canada · AC 7972 Depart at 5:25pm from Toronto (YTZ) Fly for 1h 15m Arrive at 6:40pm in Montreal (YUL)

    Layover in Montreal for 1h 10m

    Sun Mar 9th 2025 Air Canada · AC 892 Depart at 7:50pm from Montreal (YUL) Fly for 8h 10m Arrive at 9:00am in Rome (FCO)

  • US$2393
    Air TransatAir CanadaAir Canada
    12:30pm - 9:00am
    Sun Mar 16th 2025
    14h 30m
    Chicago (MDW) → Rome (FCO)
    2 Stops

    Sun Mar 16th 2025 Air Transat · TS 7058 Depart at 12:30pm from Chicago (MDW) Fly for 1h 42m Arrive at 3:12pm in Toronto (YTZ)

    Layover in Toronto for 2h 13m

    Sun Mar 16th 2025 Air Canada · AC 7972 Depart at 5:25pm from Toronto (YTZ) Fly for 1h 15m Arrive at 6:40pm in Montreal (YUL)

    Layover in Montreal for 1h 10m

    Sun Mar 16th 2025 Air Canada · AC 892 Depart at 7:50pm from Montreal (YUL) Fly for 8h 10m Arrive at 9:00am in Rome (FCO)

  • US$2396
    Air TransatAir CanadaAir Canada
    12:30pm - 9:00am
    Sun Mar 23rd 2025
    14h 30m
    Chicago (MDW) → Rome (FCO)
    2 Stops

    Sun Mar 23rd 2025 Air Transat · TS 7058 Depart at 12:30pm from Chicago (MDW) Fly for 1h 42m Arrive at 3:12pm in Toronto (YTZ)

    Layover in Toronto for 2h 13m

    Sun Mar 23rd 2025 Air Canada · AC 7972 Depart at 5:25pm from Toronto (YTZ) Fly for 1h 15m Arrive at 6:40pm in Montreal (YUL)

    Layover in Montreal for 1h 10m

    Sun Mar 23rd 2025 Air Canada · AC 892 Depart at 7:50pm from Montreal (YUL) Fly for 8h 10m Arrive at 9:00am in Rome (FCO)

  • US$2472
    Air FranceAir FranceAir France
    5:59pm - 3:40pm
    Fri Mar 7th 2025
    14h 41m
    Chicago (MDW) → Bologna (BLQ)
    2 Stops

    Fri Mar 7th 2025 Air France · AF 2651 Depart at 5:59pm from Chicago (MDW) Fly for 1h 15m Arrive at 8:14pm in Detroit (DTW)

    Layover in Detroit for 0h 56m

    Fri Mar 7th 2025 Air France · AF 377 Depart at 9:10pm from Detroit (DTW) Fly for 7h 45m Arrive at 10:55am in Paris (CDG)

    Layover in Paris for 3h 5m

    Sat Mar 8th 2025 Air France · AF 1428 Depart at 2:00pm from Paris (CDG) Fly for 1h 40m Arrive at 3:40pm in Bologna (BLQ)

  • US$2558
    Air FranceAir FranceAir France
    5:59pm - 2:35pm
    Sat Mar 22nd 2025
    14h 36m
    Chicago (MDW) → Florence (FLR)
    2 Stops

    Sat Mar 22nd 2025 Air France · AF 2651 Depart at 5:59pm from Chicago (MDW) Fly for 1h 15m Arrive at 8:14pm in Detroit (DTW)

    Layover in Detroit for 1h 56m

    Sat Mar 22nd 2025 Air France · AF 377 Depart at 10:10pm from Detroit (DTW) Fly for 7h 45m Arrive at 10:55am in Paris (CDG)

    Layover in Paris for 1h 55m

    Sun Mar 23rd 2025 Air France · AF 1566 Depart at 12:50pm from Paris (CDG) Fly for 1h 45m Arrive at 2:35pm in Florence (FLR)

  • US$2561
    Air TransatAir CanadaAir Canada
    12:30pm - 10:20am
    Sat Mar 8th 2025
    14h 50m
    Chicago (MDW) → Milan (MXP)
    2 Stops

    Sat Mar 8th 2025 Air Transat · TS 7058 Depart at 12:30pm from Chicago (MDW) Fly for 1h 42m Arrive at 3:12pm in Toronto (YTZ)

    Layover in Toronto for 2h 13m

    Sat Mar 8th 2025 Air Canada · AC 7972 Depart at 5:25pm from Toronto (YTZ) Fly for 1h 15m Arrive at 6:40pm in Montreal (YUL)

    Layover in Montreal for 1h 45m

    Sat Mar 8th 2025 Air Canada · AC 894 Depart at 8:25pm from Montreal (YUL) Fly for 7h 55m Arrive at 10:20am in Milan (MXP)

  • US$2579
    Air FranceAir FranceAir France
    5:59pm - 2:10pm
    Sat Mar 22nd 2025
    14h 11m
    Chicago (MDW) → Venice (VCE)
    2 Stops

    Sat Mar 22nd 2025 Air France · AF 2651 Depart at 5:59pm from Chicago (MDW) Fly for 1h 15m Arrive at 8:14pm in Detroit (DTW)

    Layover in Detroit for 1h 56m

    Sat Mar 22nd 2025 Air France · AF 377 Depart at 10:10pm from Detroit (DTW) Fly for 7h 45m Arrive at 10:55am in Paris (CDG)

    Layover in Paris for 1h 35m

    Sun Mar 23rd 2025 Air France · AF 1726 Depart at 12:30pm from Paris (CDG) Fly for 1h 40m Arrive at 2:10pm in Venice (VCE)

  • US$2627
    Air FranceAir FranceAir France
    5:59pm - 2:35pm
    Mon Mar 17th 2025
    14h 36m
    Chicago (MDW) → Florence (FLR)
    2 Stops

    Mon Mar 17th 2025 Air France · AF 2651 Depart at 5:59pm from Chicago (MDW) Fly for 1h 15m Arrive at 8:14pm in Detroit (DTW)

    Layover in Detroit for 1h 56m

    Mon Mar 17th 2025 Air France · AF 377 Depart at 10:10pm from Detroit (DTW) Fly for 7h 45m Arrive at 10:55am in Paris (CDG)

    Layover in Paris for 1h 55m

    Tue Mar 18th 2025 Air France · AF 1566 Depart at 12:50pm from Paris (CDG) Fly for 1h 45m Arrive at 2:35pm in Florence (FLR)

@sarahbb1
Sarah Belizaire
@sarahbb1

Have flexible travel plans or looking for alternative routes given the chaos? Check out all the connection possibilities via a super helpful site created by @ismaelyws flightlist.io thanks to @andy_travels for the recommendation #travel #flights

@eyupitsjohn
John Ford
@eyupitsjohn

There seem to be lots of sites launching at the moment that promise to find you cheap flights but not many have the professional finish of Flightlist by @ismaelyws #travel #flights

@oamingsonaa
Roaming Sonaa
@roamingsonaa

For people wanting to maximize their trips, Flightlist is my newest travel hack for uncovering the coolest routes at irresistible prices. No stress, no annoying ads — just seamless flight booking with amazing functionality.

@andy_travels
Andy Travels
@andy_travels

@ismaelyws Just tried out Flightlist for the first time. Really nice idea, well made, and just what I need at the moment 👍

@travelwitbender
Travel With Bender
@travelwitbender

Did you spot my recent article about how to score cheap one way flights? ✈️ FlightList is my new secret tool for discovering cheap routes, within a departure date range. Plus you can also search by country/region for departures & destinations. Powerful! 💪

@travel.with.wes
Wesley Mergard
@travel.with.wes

One useful tool I've found for evaluating different departure and return dates is called FlightList.io. You can quickly scan different travel date ranges, carriers and one way flight options to easily determine the cheapest flight combinations for your trip.

Explore Flight Options

FlightList Blog

Flightlist Interviews 7 Travel Experts On Why They Book One Way Flights
Flightlist Interviews 7 Travel Experts On Why They Book One Way Flights
Why I built FlightList & solved my own problem
Why I Built FlightList & Solved My Own Problem

Why I Built FlightList

❝As someone who works remotely & travels frequently, I always book one way flights and I'm flexible on my departure dates. I look for the best deals. Most sites require you to enter a specific departure date and clutter the page with uneccessary options, images and ads. I wanted something simple and minimal which allowed me to search by departure date range and display a list of flights with the ability to filter according to my needs. I built FlightList to solve my own problem and help other travelers who may have the same frustration. It's how I imagine a flight booking site should be.❞

- Hans Desjarlais, Founder & Creator Hans Desjarlais