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Flights from Orlando to Chicago (ORL to MDW)

Discover alternate routes & cheap one way flights from Orlando to Chicago (ORL to MDW) within a departure date range.

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  • USD 63
    Frontier Airlines
    7:35am - 9:31am
    Thu Jun 27th
    2h 56m
    Orlando (MCO) → Chicago (MDW)
    Direct

    Thu Jun 27th 2024 Frontier Airlines · F9 1457 Depart at 7:35am from Orlando (MCO) Fly for 2h 56m Arrive at 9:31am in Chicago (MDW)

  • USD 69
    Frontier Airlines
    11:47am - 10:58pm
    Wed Jun 19th
    12h 11m
    Orlando (MCO) → Chicago (MDW)
    1 Stop

    Wed Jun 19th 2024 Frontier Airlines · F9 1554 Depart at 11:47am from Orlando (MCO) Fly for 1h 54m Arrive at 1:41pm in Raleigh (RDU)

    Layover in Raleigh for 8h 17m

    Wed Jun 19th 2024 Frontier Airlines · F9 3717 Depart at 9:58pm from Raleigh (RDU) Fly for 2h 0m Arrive at 10:58pm in Chicago (MDW)

  • USD 69
    Frontier Airlines
    6:30am - 10:58pm
    Wed Jun 19th
    17h 28m
    Orlando (MCO) → Chicago (MDW)
    1 Stop

    Wed Jun 19th 2024 Frontier Airlines · F9 1234 Depart at 6:30am from Orlando (MCO) Fly for 1h 53m Arrive at 8:23am in Raleigh (RDU)

    Layover in Raleigh for 13h 35m

    Wed Jun 19th 2024 Frontier Airlines · F9 3717 Depart at 9:58pm from Raleigh (RDU) Fly for 2h 0m Arrive at 10:58pm in Chicago (MDW)

  • USD 76
    Frontier Airlines
    8:00am - 9:20pm
    Tue Jun 18th
    14h 20m
    Orlando (MCO) → Chicago (MDW)
    2 Stops

    Tue Jun 18th 2024 Frontier Airlines · F9 1686 Depart at 8:00am from Orlando (MCO) Fly for 1h 52m Arrive at 9:52am in Raleigh (RDU)

    Layover in Raleigh for 7h 55m

    Tue Jun 18th 2024 Frontier Airlines · F9 1617 Depart at 5:47pm from Raleigh (RDU) Fly for 1h 29m Arrive at 7:16pm in Philadelphia (PHL)

    Layover in Philadelphia for 0h 52m

    Tue Jun 18th 2024 Frontier Airlines · F9 1617 Depart at 8:08pm from Philadelphia (PHL) Fly for 2h 12m Arrive at 9:20pm in Chicago (MDW)

  • USD 76
    Frontier Airlines
    6:00am - 9:20pm
    Tue Jun 18th
    16h 20m
    Orlando (MCO) → Chicago (MDW)
    2 Stops

    Tue Jun 18th 2024 Frontier Airlines · F9 1040 Depart at 6:00am from Orlando (MCO) Fly for 1h 53m Arrive at 7:53am in Raleigh (RDU)

    Layover in Raleigh for 9h 54m

    Tue Jun 18th 2024 Frontier Airlines · F9 1617 Depart at 5:47pm from Raleigh (RDU) Fly for 1h 29m Arrive at 7:16pm in Philadelphia (PHL)

    Layover in Philadelphia for 0h 52m

    Tue Jun 18th 2024 Frontier Airlines · F9 1617 Depart at 8:08pm from Philadelphia (PHL) Fly for 2h 12m Arrive at 9:20pm in Chicago (MDW)

  • USD 91
    Frontier Airlines
    10:20am - 12:05pm
    Fri Jul 5th
    2h 45m
    Orlando (MCO) → Chicago (MDW)
    Direct

    Fri Jul 5th 2024 Frontier Airlines · F9 1457 Depart at 10:20am from Orlando (MCO) Fly for 2h 45m Arrive at 12:05pm in Chicago (MDW)

  • USD 95
    Frontier Airlines
    10:20am - 12:13pm
    Fri Jun 28th
    2h 53m
    Orlando (MCO) → Chicago (MDW)
    Direct

    Fri Jun 28th 2024 Frontier Airlines · F9 1457 Depart at 10:20am from Orlando (MCO) Fly for 2h 53m Arrive at 12:13pm in Chicago (MDW)

  • USD 96
    Frontier Airlines
    6:00am - 7:55am
    Sat Jun 22nd
    2h 55m
    Orlando (MCO) → Chicago (MDW)
    Direct

    Sat Jun 22nd 2024 Frontier Airlines · F9 1457 Depart at 6:00am from Orlando (MCO) Fly for 2h 55m Arrive at 7:55am in Chicago (MDW)

  • USD 103
    Frontier Airlines
    9:15am - 11:10am
    Mon Jun 24th
    2h 55m
    Orlando (MCO) → Chicago (MDW)
    Direct

    Mon Jun 24th 2024 Frontier Airlines · F9 1457 Depart at 9:15am from Orlando (MCO) Fly for 2h 55m Arrive at 11:10am in Chicago (MDW)

  • USD 107
    Frontier Airlines
    7:35am - 9:31am
    Thu Jun 20th
    2h 56m
    Orlando (MCO) → Chicago (MDW)
    Direct

    Thu Jun 20th 2024 Frontier Airlines · F9 1457 Depart at 7:35am from Orlando (MCO) Fly for 2h 56m Arrive at 9:31am in Chicago (MDW)

  • USD 114
    Frontier Airlines
    6:30am - 10:58pm
    Wed Jun 12th
    17h 28m
    Orlando (MCO) → Chicago (MDW)
    1 Stop

    Wed Jun 12th 2024 Frontier Airlines · F9 1234 Depart at 6:30am from Orlando (MCO) Fly for 1h 53m Arrive at 8:23am in Raleigh (RDU)

    Layover in Raleigh for 13h 35m

    Wed Jun 12th 2024 Frontier Airlines · F9 3717 Depart at 9:58pm from Raleigh (RDU) Fly for 2h 0m Arrive at 10:58pm in Chicago (MDW)

  • USD 114
    Frontier Airlines
    8:57pm - 5:10pm
    Mon Jun 17th
    21h 13m
    Orlando (MCO) → Chicago (MDW)
    1 Stop

    Mon Jun 17th 2024 Frontier Airlines · F9 3311 Depart at 8:57pm from Orlando (MCO) Fly for 4h 16m Arrive at 11:13pm in Denver (DEN)

    Layover in Denver for 14h 33m

    Tue Jun 18th 2024 Frontier Airlines · F9 2946 Depart at 1:46pm from Denver (DEN) Fly for 2h 24m Arrive at 5:10pm in Chicago (MDW)

  • USD 120
    Frontier Airlines
    6:00am - 7:45am
    Sat Jul 6th
    2h 45m
    Orlando (MCO) → Chicago (MDW)
    Direct

    Sat Jul 6th 2024 Frontier Airlines · F9 1457 Depart at 6:00am from Orlando (MCO) Fly for 2h 45m Arrive at 7:45am in Chicago (MDW)

  • USD 120
    Frontier Airlines
    6:00am - 7:55am
    Sat Jun 29th
    2h 55m
    Orlando (MCO) → Chicago (MDW)
    Direct

    Sat Jun 29th 2024 Frontier Airlines · F9 1457 Depart at 6:00am from Orlando (MCO) Fly for 2h 55m Arrive at 7:55am in Chicago (MDW)

  • USD 120
    Frontier Airlines
    9:15am - 11:10am
    Mon Jul 1st
    2h 55m
    Orlando (MCO) → Chicago (MDW)
    Direct

    Mon Jul 1st 2024 Frontier Airlines · F9 1457 Depart at 9:15am from Orlando (MCO) Fly for 2h 55m Arrive at 11:10am in Chicago (MDW)

  • USD 122
    Frontier Airlines
    6:00am - 7:55am
    Sat Jun 15th
    2h 55m
    Orlando (MCO) → Chicago (MDW)
    Direct

    Sat Jun 15th 2024 Frontier Airlines · F9 1457 Depart at 6:00am from Orlando (MCO) Fly for 2h 55m Arrive at 7:55am in Chicago (MDW)

  • USD 130
    Frontier Airlines
    5:20pm - 11:06pm
    Tue Jun 18th
    6h 46m
    Orlando (MCO) → Chicago (MDW)
    1 Stop

    Tue Jun 18th 2024 Frontier Airlines · F9 4025 Depart at 5:20pm from Orlando (MCO) Fly for 1h 49m Arrive at 7:09pm in Atlanta (ATL)

    Layover in Atlanta for 2h 57m

    Tue Jun 18th 2024 Frontier Airlines · F9 2291 Depart at 10:06pm from Atlanta (ATL) Fly for 2h 0m Arrive at 11:06pm in Chicago (MDW)

  • USD 130
    Frontier Airlines
    3:25pm - 10:58pm
    Sat Jun 15th
    8h 33m
    Orlando (MCO) → Chicago (MDW)
    1 Stop

    Sat Jun 15th 2024 Frontier Airlines · F9 3469 Depart at 3:25pm from Orlando (MCO) Fly for 2h 45m Arrive at 5:10pm in Houston (IAH)

    Layover in Houston for 3h 20m

    Sat Jun 15th 2024 Frontier Airlines · F9 1398 Depart at 8:30pm from Houston (IAH) Fly for 2h 28m Arrive at 10:58pm in Chicago (MDW)

  • USD 136
    Frontier Airlines
    6:35am - 10:58pm
    Mon Jun 17th
    17h 23m
    Orlando (MCO) → Chicago (MDW)
    1 Stop

    Mon Jun 17th 2024 Frontier Airlines · F9 1234 Depart at 6:35am from Orlando (MCO) Fly for 1h 53m Arrive at 8:28am in Raleigh (RDU)

    Layover in Raleigh for 13h 30m

    Mon Jun 17th 2024 Frontier Airlines · F9 3717 Depart at 9:58pm from Raleigh (RDU) Fly for 2h 0m Arrive at 10:58pm in Chicago (MDW)

  • USD 136
    Frontier Airlines
    3:25pm - 1:30pm
    Sat Jun 15th
    23h 5m
    Orlando (MCO) → Chicago (MDW)
    1 Stop

    Sat Jun 15th 2024 Frontier Airlines · F9 3469 Depart at 3:25pm from Orlando (MCO) Fly for 2h 45m Arrive at 5:10pm in Houston (IAH)

    Layover in Houston for 17h 52m

    Sun Jun 16th 2024 Frontier Airlines · F9 3282 Depart at 11:02am from Houston (IAH) Fly for 2h 28m Arrive at 1:30pm in Chicago (MDW)

  • USD 141
    Frontier Airlines
    7:35am - 9:31am
    Thu Jul 4th
    2h 56m
    Orlando (MCO) → Chicago (MDW)
    Direct

    Thu Jul 4th 2024 Frontier Airlines · F9 1457 Depart at 7:35am from Orlando (MCO) Fly for 2h 56m Arrive at 9:31am in Chicago (MDW)

  • USD 151
    Frontier Airlines
    8:00am - 4:16pm
    Mon Jun 17th
    9h 16m
    Orlando (MCO) → Chicago (MDW)
    1 Stop

    Mon Jun 17th 2024 Frontier Airlines · F9 1481 Depart at 8:00am from Orlando (MCO) Fly for 3h 6m Arrive at 10:06am in Dallas (DFW)

    Layover in Dallas for 3h 49m

    Mon Jun 17th 2024 Frontier Airlines · F9 3000 Depart at 1:55pm from Dallas (DFW) Fly for 2h 21m Arrive at 4:16pm in Chicago (MDW)

  • USD 154
    Frontier Airlines
    5:30am - 8:07pm
    Wed Jun 19th
    15h 37m
    Orlando (MCO) → Chicago (MDW)
    1 Stop

    Wed Jun 19th 2024 Frontier Airlines · F9 3274 Depart at 5:30am from Orlando (MCO) Fly for 2h 17m Arrive at 7:47am in Washington, D.C. (BWI)

    Layover in Washington, D.C. for 11h 22m

    Wed Jun 19th 2024 Frontier Airlines · F9 2331 Depart at 7:09pm from Washington, D.C. (BWI) Fly for 1h 58m Arrive at 8:07pm in Chicago (MDW)

  • USD 154
    Frontier Airlines
    7:06pm - 1:40pm
    Wed Jun 19th
    19h 34m
    Orlando (MCO) → Chicago (MDW)
    1 Stop

    Wed Jun 19th 2024 Frontier Airlines · F9 3469 Depart at 7:06pm from Orlando (MCO) Fly for 2h 47m Arrive at 8:53pm in Houston (IAH)

    Layover in Houston for 14h 19m

    Thu Jun 20th 2024 Frontier Airlines · F9 3282 Depart at 11:12am from Houston (IAH) Fly for 2h 28m Arrive at 1:40pm in Chicago (MDW)

  • USD 157
    Frontier Airlines
    5:15am - 1:38pm
    Mon Jun 17th
    9h 23m
    Orlando (MCO) → Chicago (MDW)
    1 Stop

    Mon Jun 17th 2024 Frontier Airlines · F9 1542 Depart at 5:15am from Orlando (MCO) Fly for 2h 34m Arrive at 7:49am in Philadelphia (PHL)

    Layover in Philadelphia for 4h 38m

    Mon Jun 17th 2024 Frontier Airlines · F9 4367 Depart at 12:27pm from Philadelphia (PHL) Fly for 2h 11m Arrive at 1:38pm in Chicago (MDW)

  • USD 157
    Frontier Airlines
    11:47am - 10:58pm
    Wed Jun 12th
    12h 11m
    Orlando (MCO) → Chicago (MDW)
    1 Stop

    Wed Jun 12th 2024 Frontier Airlines · F9 1554 Depart at 11:47am from Orlando (MCO) Fly for 1h 54m Arrive at 1:41pm in Raleigh (RDU)

    Layover in Raleigh for 8h 17m

    Wed Jun 12th 2024 Frontier Airlines · F9 3717 Depart at 9:58pm from Raleigh (RDU) Fly for 2h 0m Arrive at 10:58pm in Chicago (MDW)

  • USD 157
    Frontier Airlines
    8:59pm - 12:00pm
    Tue Jun 18th
    16h 1m
    Orlando (MCO) → Chicago (MDW)
    1 Stop

    Tue Jun 18th 2024 Frontier Airlines · F9 3311 Depart at 8:59pm from Orlando (MCO) Fly for 4h 16m Arrive at 11:15pm in Denver (DEN)

    Layover in Denver for 9h 23m

    Wed Jun 19th 2024 Frontier Airlines · F9 2210 Depart at 8:38am from Denver (DEN) Fly for 2h 22m Arrive at 12:00pm in Chicago (MDW)

  • USD 157
    Frontier Airlines
    8:57pm - 12:00pm
    Sun Jun 16th
    16h 3m
    Orlando (MCO) → Chicago (MDW)
    1 Stop

    Sun Jun 16th 2024 Frontier Airlines · F9 3311 Depart at 8:57pm from Orlando (MCO) Fly for 4h 16m Arrive at 11:13pm in Denver (DEN)

    Layover in Denver for 9h 25m

    Mon Jun 17th 2024 Frontier Airlines · F9 2210 Depart at 8:38am from Denver (DEN) Fly for 2h 22m Arrive at 12:00pm in Chicago (MDW)

  • USD 157
    Frontier Airlines
    8:57pm - 1:09pm
    Mon Jun 17th
    17h 12m
    Orlando (MCO) → Chicago (MDW)
    1 Stop

    Mon Jun 17th 2024 Frontier Airlines · F9 3311 Depart at 8:57pm from Orlando (MCO) Fly for 4h 16m Arrive at 11:13pm in Denver (DEN)

    Layover in Denver for 10h 32m

    Tue Jun 18th 2024 Frontier Airlines · F9 2210 Depart at 9:45am from Denver (DEN) Fly for 2h 24m Arrive at 1:09pm in Chicago (MDW)

  • USD 157
    Frontier Airlines
    6:30am - 10:58pm
    Fri Jun 14th
    17h 28m
    Orlando (MCO) → Chicago (MDW)
    1 Stop

    Fri Jun 14th 2024 Frontier Airlines · F9 1234 Depart at 6:30am from Orlando (MCO) Fly for 1h 53m Arrive at 8:23am in Raleigh (RDU)

    Layover in Raleigh for 13h 35m

    Fri Jun 14th 2024 Frontier Airlines · F9 3717 Depart at 9:58pm from Raleigh (RDU) Fly for 2h 0m Arrive at 10:58pm in Chicago (MDW)

  • USD 157
    Frontier Airlines
    8:20am - 5:21am
    Sat Jun 15th
    22h 1m
    Orlando (MCO) → Chicago (MDW)
    1 Stop

    Sat Jun 15th 2024 Frontier Airlines · F9 1875 Depart at 8:20am from Orlando (MCO) Fly for 5h 7m Arrive at 10:27am in Las Vegas (LAS)

    Layover in Las Vegas for 13h 21m

    Sat Jun 15th 2024 Frontier Airlines · F9 2330 Depart at 11:48pm from Las Vegas (LAS) Fly for 3h 33m Arrive at 5:21am in Chicago (MDW)

  • USD 166
    Frontier Airlines
    9:20am - 11:05am
    Mon Jul 8th
    2h 45m
    Orlando (MCO) → Chicago (MDW)
    Direct

    Mon Jul 8th 2024 Frontier Airlines · F9 1457 Depart at 9:20am from Orlando (MCO) Fly for 2h 45m Arrive at 11:05am in Chicago (MDW)

  • USD 169
    Frontier Airlines
    9:15am - 11:10am
    Mon Jun 17th
    2h 55m
    Orlando (MCO) → Chicago (MDW)
    Direct

    Mon Jun 17th 2024 Frontier Airlines · F9 1457 Depart at 9:15am from Orlando (MCO) Fly for 2h 55m Arrive at 11:10am in Chicago (MDW)

  • USD 169
    Frontier Airlines
    3:20pm - 5:15pm
    Fri Jun 14th
    2h 55m
    Orlando (MCO) → Chicago (MDW)
    Direct

    Fri Jun 14th 2024 Frontier Airlines · F9 1457 Depart at 3:20pm from Orlando (MCO) Fly for 2h 55m Arrive at 5:15pm in Chicago (MDW)

  • USD 169
    Frontier Airlines
    7:35am - 9:31am
    Sun Jun 16th
    2h 56m
    Orlando (MCO) → Chicago (MDW)
    Direct

    Sun Jun 16th 2024 Frontier Airlines · F9 1457 Depart at 7:35am from Orlando (MCO) Fly for 2h 56m Arrive at 9:31am in Chicago (MDW)

  • USD 191
    Frontier Airlines
    7:35am - 9:20am
    Sun Jul 7th
    2h 45m
    Orlando (MCO) → Chicago (MDW)
    Direct

    Sun Jul 7th 2024 Frontier Airlines · F9 1457 Depart at 7:35am from Orlando (MCO) Fly for 2h 45m Arrive at 9:20am in Chicago (MDW)

  • USD 197
    Frontier Airlines
    8:35am - 7:56pm
    Thu Jun 20th
    12h 21m
    Orlando (MCO) → Chicago (MDW)
    1 Stop

    Thu Jun 20th 2024 Frontier Airlines · F9 2416 Depart at 8:35am from Orlando (MCO) Fly for 2h 37m Arrive at 11:12am in Philadelphia (PHL)

    Layover in Philadelphia for 7h 30m

    Thu Jun 20th 2024 Frontier Airlines · F9 4367 Depart at 6:42pm from Philadelphia (PHL) Fly for 2h 14m Arrive at 7:56pm in Chicago (MDW)

  • USD 219
    Frontier Airlines
    7:35am - 9:31am
    Sun Jun 23rd
    2h 56m
    Orlando (MCO) → Chicago (MDW)
    Direct

    Sun Jun 23rd 2024 Frontier Airlines · F9 1457 Depart at 7:35am from Orlando (MCO) Fly for 2h 56m Arrive at 9:31am in Chicago (MDW)

  • USD 223
    Frontier Airlines
    7:35am - 9:31am
    Thu Jun 13th
    2h 56m
    Orlando (MCO) → Chicago (MDW)
    Direct

    Thu Jun 13th 2024 Frontier Airlines · F9 1457 Depart at 7:35am from Orlando (MCO) Fly for 2h 56m Arrive at 9:31am in Chicago (MDW)

  • USD 223
    Frontier Airlines
    8:00am - 2:34pm
    Wed Jun 19th
    7h 34m
    Orlando (MCO) → Chicago (MDW)
    1 Stop

    Wed Jun 19th 2024 Frontier Airlines · F9 1563 Depart at 8:00am from Orlando (MCO) Fly for 1h 44m Arrive at 9:44am in Atlanta (ATL)

    Layover in Atlanta for 3h 50m

    Wed Jun 19th 2024 Frontier Airlines · F9 2143 Depart at 1:34pm from Atlanta (ATL) Fly for 2h 0m Arrive at 2:34pm in Chicago (MDW)

  • USD 223
    Frontier Airlines
    3:48pm - 10:30pm
    Wed Jun 19th
    7h 42m
    Orlando (MCO) → Chicago (MDW)
    1 Stop

    Wed Jun 19th 2024 Frontier Airlines · F9 1951 Depart at 3:48pm from Orlando (MCO) Fly for 3h 14m Arrive at 6:02pm in Dallas (DFW)

    Layover in Dallas for 2h 10m

    Wed Jun 19th 2024 Frontier Airlines · F9 2882 Depart at 8:12pm from Dallas (DFW) Fly for 2h 18m Arrive at 10:30pm in Chicago (MDW)

  • USD 226
    Frontier Airlines
    3:08pm - 7:56pm
    Thu Jun 20th
    5h 48m
    Orlando (MCO) → Chicago (MDW)
    1 Stop

    Thu Jun 20th 2024 Frontier Airlines · F9 4367 Depart at 3:08pm from Orlando (MCO) Fly for 2h 44m Arrive at 5:52pm in Philadelphia (PHL)

    Layover in Philadelphia for 0h 50m

    Thu Jun 20th 2024 Frontier Airlines · F9 4367 Depart at 6:42pm from Philadelphia (PHL) Fly for 2h 14m Arrive at 7:56pm in Chicago (MDW)

  • USD 227
    Frontier Airlines
    12:15pm - 6:39pm
    Tue Jun 18th
    7h 24m
    Orlando (MCO) → Chicago (MDW)
    1 Stop

    Tue Jun 18th 2024 Frontier Airlines · F9 1306 Depart at 12:15pm from Orlando (MCO) Fly for 1h 42m Arrive at 1:57pm in Atlanta (ATL)

    Layover in Atlanta for 3h 41m

    Tue Jun 18th 2024 Frontier Airlines · F9 2779 Depart at 5:38pm from Atlanta (ATL) Fly for 2h 1m Arrive at 6:39pm in Chicago (MDW)

  • USD 233
    Frontier Airlines
    7:05am - 5:10pm
    Tue Jun 18th
    11h 5m
    Orlando (MCO) → Chicago (MDW)
    1 Stop

    Tue Jun 18th 2024 Frontier Airlines · F9 1733 Depart at 7:05am from Orlando (MCO) Fly for 4h 9m Arrive at 9:14am in Denver (DEN)

    Layover in Denver for 4h 32m

    Tue Jun 18th 2024 Frontier Airlines · F9 2946 Depart at 1:46pm from Denver (DEN) Fly for 2h 24m Arrive at 5:10pm in Chicago (MDW)

  • USD 238
    Frontier Airlines
    8:49am - 1:32pm
    Wed Jun 12th
    5h 43m
    Orlando (MCO) → Chicago (MDW)
    1 Stop

    Wed Jun 12th 2024 Frontier Airlines · F9 2416 Depart at 8:49am from Orlando (MCO) Fly for 2h 37m Arrive at 11:26am in Philadelphia (PHL)

    Layover in Philadelphia for 0h 55m

    Wed Jun 12th 2024 Frontier Airlines · F9 4367 Depart at 12:21pm from Philadelphia (PHL) Fly for 2h 11m Arrive at 1:32pm in Chicago (MDW)

  • USD 241
    Frontier Airlines
    3:08pm - 7:56pm
    Thu Jun 13th
    5h 48m
    Orlando (MCO) → Chicago (MDW)
    1 Stop

    Thu Jun 13th 2024 Frontier Airlines · F9 4367 Depart at 3:08pm from Orlando (MCO) Fly for 2h 44m Arrive at 5:52pm in Philadelphia (PHL)

    Layover in Philadelphia for 0h 50m

    Thu Jun 13th 2024 Frontier Airlines · F9 4367 Depart at 6:42pm from Philadelphia (PHL) Fly for 2h 14m Arrive at 7:56pm in Chicago (MDW)

  • USD 255
    Frontier Airlines
    12:09pm - 4:51pm
    Thu Jun 20th
    5h 42m
    Orlando (MCO) → Chicago (MDW)
    1 Stop

    Thu Jun 20th 2024 Frontier Airlines · F9 2898 Depart at 12:09pm from Orlando (MCO) Fly for 1h 42m Arrive at 1:51pm in Atlanta (ATL)

    Layover in Atlanta for 2h 0m

    Thu Jun 20th 2024 Frontier Airlines · F9 2779 Depart at 3:51pm from Atlanta (ATL) Fly for 2h 0m Arrive at 4:51pm in Chicago (MDW)

  • USD 255
    Frontier Airlines
    8:49am - 1:32pm
    Wed Jun 19th
    5h 43m
    Orlando (MCO) → Chicago (MDW)
    1 Stop

    Wed Jun 19th 2024 Frontier Airlines · F9 2416 Depart at 8:49am from Orlando (MCO) Fly for 2h 37m Arrive at 11:26am in Philadelphia (PHL)

    Layover in Philadelphia for 0h 55m

    Wed Jun 19th 2024 Frontier Airlines · F9 4367 Depart at 12:21pm from Philadelphia (PHL) Fly for 2h 11m Arrive at 1:32pm in Chicago (MDW)

  • USD 260
    Frontier Airlines
    3:52pm - 9:20pm
    Tue Jun 18th
    6h 28m
    Orlando (MCO) → Chicago (MDW)
    1 Stop

    Tue Jun 18th 2024 Frontier Airlines · F9 3856 Depart at 3:52pm from Orlando (MCO) Fly for 2h 44m Arrive at 6:36pm in Philadelphia (PHL)

    Layover in Philadelphia for 1h 32m

    Tue Jun 18th 2024 Frontier Airlines · F9 1617 Depart at 8:08pm from Philadelphia (PHL) Fly for 2h 12m Arrive at 9:20pm in Chicago (MDW)

  • USD 260
    Frontier Airlines
    9:00am - 2:34pm
    Mon Jun 17th
    6h 34m
    Orlando (MCO) → Chicago (MDW)
    1 Stop

    Mon Jun 17th 2024 Frontier Airlines · F9 1563 Depart at 9:00am from Orlando (MCO) Fly for 1h 44m Arrive at 10:44am in Atlanta (ATL)

    Layover in Atlanta for 2h 50m

    Mon Jun 17th 2024 Frontier Airlines · F9 2143 Depart at 1:34pm from Atlanta (ATL) Fly for 2h 0m Arrive at 2:34pm in Chicago (MDW)

  • USD 266
    Frontier Airlines
    11:49am - 10:58pm
    Mon Jun 17th
    12h 9m
    Orlando (MCO) → Chicago (MDW)
    1 Stop

    Mon Jun 17th 2024 Frontier Airlines · F9 1554 Depart at 11:49am from Orlando (MCO) Fly for 1h 54m Arrive at 1:43pm in Raleigh (RDU)

    Layover in Raleigh for 8h 15m

    Mon Jun 17th 2024 Frontier Airlines · F9 3717 Depart at 9:58pm from Raleigh (RDU) Fly for 2h 0m Arrive at 10:58pm in Chicago (MDW)

  • USD 271
    Frontier Airlines
    8:00am - 2:34pm
    Wed Jun 12th
    7h 34m
    Orlando (MCO) → Chicago (MDW)
    1 Stop

    Wed Jun 12th 2024 Frontier Airlines · F9 1563 Depart at 8:00am from Orlando (MCO) Fly for 1h 44m Arrive at 9:44am in Atlanta (ATL)

    Layover in Atlanta for 3h 50m

    Wed Jun 12th 2024 Frontier Airlines · F9 2143 Depart at 1:34pm from Atlanta (ATL) Fly for 2h 0m Arrive at 2:34pm in Chicago (MDW)

@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

@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! 💪

Explore Flight Options

Cheap Flight Search Tips

Tips to help you find the cheapest flights from Orlando to Chicago (ORL to MDW).

  • Book 45-90 days before your departure date.
  • Fly during weekdays (Monday-Thursday).
  • Airfare Sales: Airlines sometimes offer huge discounts and since we take a bottom-up approach these flights will appear first in the results, so check back regularly because they don't usually last long.

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 want something simple and minimal which allows me to search by departure date range & display a list of flights with the ability to filter according to my needs. So, I built FlightList to solve my own problem & 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