Flights from Port of Spain to Chicago (POS to MDW)

Discover more affordable routes and cheaper dates from Port of Spain to Chicago (POS to MDW) within a date range.

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  • US$528
    Caribbean AirlinesFrontier AirlinesFrontier Airlines
    9:10am - 12:13am
    Mon Dec 2nd 2024
    41h 3m
    Port of Spain (POS) → Chicago (MDW)
    2 Stops

    Mon Dec 2nd 2024 Caribbean Airlines · BW 484 Depart at 9:10am from Port of Spain (POS) Fly for 4h 5m Arrive at 12:15pm in Miami (MIA)

    Layover in Miami for 19h 50m

    Tue Dec 3rd 2024 Frontier Airlines · F9 3137 Depart at 8:05am from Miami (MIA) Fly for 4h 43m Arrive at 10:48am in Denver (DEN)

    Layover in Denver for 10h 7m

    Tue Dec 3rd 2024 Frontier Airlines · F9 2210 Depart at 8:55pm from Denver (DEN) Fly for 2h 18m Arrive at 12:13am in Chicago (MDW)

  • US$761
    Caribbean AirlinesWestJetWestJet
    8:50am - 9:46pm
    Mon Dec 2nd 2024
    38h 56m
    Port of Spain (POS) → Chicago (MDW)
    2 Stops

    Mon Dec 2nd 2024 Caribbean Airlines · BW 612 Depart at 8:50am from Port of Spain (POS) Fly for 6h 5m Arrive at 1:55pm in Toronto (YYZ)

    Layover in Toronto for 22h 26m

    Tue Dec 3rd 2024 WestJet · WS 6342 Depart at 12:21pm from Toronto (YYZ) Fly for 2h 17m Arrive at 2:38pm in Atlanta (ATL)

    Layover in Atlanta for 6h 12m

    Tue Dec 3rd 2024 WestJet · WS 6664 Depart at 8:50pm from Atlanta (ATL) Fly for 1h 56m Arrive at 9:46pm in Chicago (MDW)

  • US$772
    Caribbean AirlinesFrontier AirlinesFrontier Airlines
    9:10am - 9:59pm
    Mon Dec 2nd 2024
    14h 49m
    Port of Spain (POS) → Chicago (MDW)
    2 Stops

    Mon Dec 2nd 2024 Caribbean Airlines · BW 484 Depart at 9:10am from Port of Spain (POS) Fly for 4h 5m Arrive at 12:15pm in Miami (MIA)

    Layover in Miami for 2h 52m

    Mon Dec 2nd 2024 Frontier Airlines · F9 2675 Depart at 3:07pm from Miami (MIA) Fly for 3h 31m Arrive at 5:38pm in Dallas (DFW)

    Layover in Dallas for 1h 57m

    Mon Dec 2nd 2024 Frontier Airlines · F9 2998 Depart at 7:35pm from Dallas (DFW) Fly for 2h 24m Arrive at 9:59pm in Chicago (MDW)

  • US$772
    Caribbean AirlinesFrontier AirlinesFrontier Airlines
    9:10am - 11:08pm
    Mon Dec 2nd 2024
    15h 58m
    Port of Spain (POS) → Chicago (MDW)
    2 Stops

    Mon Dec 2nd 2024 Caribbean Airlines · BW 484 Depart at 9:10am from Port of Spain (POS) Fly for 4h 5m Arrive at 12:15pm in Miami (MIA)

    Layover in Miami for 6h 4m

    Mon Dec 2nd 2024 Frontier Airlines · F9 3441 Depart at 6:19pm from Miami (MIA) Fly for 2h 16m Arrive at 8:35pm in Atlanta (ATL)

    Layover in Atlanta for 1h 36m

    Mon Dec 2nd 2024 Frontier Airlines · F9 2779 Depart at 10:11pm from Atlanta (ATL) Fly for 1h 57m Arrive at 11:08pm in Chicago (MDW)

  • US$772
    Caribbean AirlinesFrontier AirlinesFrontier Airlines
    9:10am - 11:10am
    Sun Dec 1st 2024
    28h 0m
    Port of Spain (POS) → Chicago (MDW)
    2 Stops

    Sun Dec 1st 2024 Caribbean Airlines · BW 484 Depart at 9:10am from Port of Spain (POS) Fly for 4h 5m Arrive at 12:15pm in Miami (MIA)

    Layover in Miami for 17h 55m

    Mon Dec 2nd 2024 Frontier Airlines · F9 4405 Depart at 6:10am from Miami (MIA) Fly for 2h 12m Arrive at 8:22am in Atlanta (ATL)

    Layover in Atlanta for 1h 46m

    Mon Dec 2nd 2024 Frontier Airlines · F9 2143 Depart at 10:08am from Atlanta (ATL) Fly for 2h 2m Arrive at 11:10am in Chicago (MDW)

  • US$778
    Caribbean AirlinesFrontier AirlinesFrontier Airlines
    9:10am - 12:13am
    Mon Dec 2nd 2024
    41h 3m
    Port of Spain (POS) → Chicago (MDW)
    2 Stops

    Mon Dec 2nd 2024 Caribbean Airlines · BW 484 Depart at 9:10am from Port of Spain (POS) Fly for 4h 5m Arrive at 12:15pm in Miami (MIA)

    Layover in Miami for 10h 33m

    Mon Dec 2nd 2024 Frontier Airlines · F9 1279 Depart at 10:48pm from Miami (MIA) Fly for 4h 37m Arrive at 1:25am in Denver (DEN)

    Layover in Denver for 19h 30m

    Tue Dec 3rd 2024 Frontier Airlines · F9 2210 Depart at 8:55pm from Denver (DEN) Fly for 2h 18m Arrive at 12:13am in Chicago (MDW)

  • US$794
    Caribbean AirlinesFrontier AirlinesFrontier Airlines
    8:30am - 11:08pm
    Mon Dec 2nd 2024
    16h 38m
    Port of Spain (POS) → Chicago (MDW)
    2 Stops

    Mon Dec 2nd 2024 Caribbean Airlines · BW 482 Depart at 8:30am from Port of Spain (POS) Fly for 4h 30m Arrive at 12:00pm in Orlando (MCO)

    Layover in Orlando for 6h 34m

    Mon Dec 2nd 2024 Frontier Airlines · F9 4555 Depart at 6:34pm from Orlando (MCO) Fly for 1h 52m Arrive at 8:26pm in Atlanta (ATL)

    Layover in Atlanta for 1h 45m

    Mon Dec 2nd 2024 Frontier Airlines · F9 2779 Depart at 10:11pm from Atlanta (ATL) Fly for 1h 57m Arrive at 11:08pm in Chicago (MDW)

  • US$806
    Copa AirlinesCopa AirlinesFrontier Airlines
    3:38am - 11:58pm
    Sun Dec 1st 2024
    22h 20m
    Port of Spain (POS) → Chicago (MDW)
    2 Stops

    Sun Dec 1st 2024 Copa Airlines · CM 315 Depart at 3:38am from Port of Spain (POS) Fly for 3h 16m Arrive at 5:54am in Panama (PTY)

    Layover in Panama for 3h 31m

    Sun Dec 1st 2024 Copa Airlines · CM 880 Depart at 9:25am from Panama (PTY) Fly for 4h 24m Arrive at 1:49pm in Atlanta (ATL)

    Layover in Atlanta for 9h 11m

    Sun Dec 1st 2024 Frontier Airlines · F9 2291 Depart at 11:00pm from Atlanta (ATL) Fly for 1h 58m Arrive at 11:58pm in Chicago (MDW)

  • US$806
    Copa AirlinesCopa AirlinesFrontier Airlines
    3:38am - 11:10am
    Sun Dec 1st 2024
    33h 32m
    Port of Spain (POS) → Chicago (MDW)
    2 Stops

    Sun Dec 1st 2024 Copa Airlines · CM 315 Depart at 3:38am from Port of Spain (POS) Fly for 3h 16m Arrive at 5:54am in Panama (PTY)

    Layover in Panama for 3h 31m

    Sun Dec 1st 2024 Copa Airlines · CM 880 Depart at 9:25am from Panama (PTY) Fly for 4h 24m Arrive at 1:49pm in Atlanta (ATL)

    Layover in Atlanta for 20h 19m

    Mon Dec 2nd 2024 Frontier Airlines · F9 2143 Depart at 10:08am from Atlanta (ATL) Fly for 2h 2m Arrive at 11:10am in Chicago (MDW)

  • US$846
    Caribbean AirlinesWestJetWestJet
    8:15am - 5:54pm
    Sun Dec 1st 2024
    35h 39m
    Port of Spain (POS) → Chicago (MDW)
    2 Stops

    Sun Dec 1st 2024 Caribbean Airlines · BW 610 Depart at 8:15am from Port of Spain (POS) Fly for 6h 5m Arrive at 1:20pm in Toronto (YYZ)

    Layover in Toronto for 18h 30m

    Mon Dec 2nd 2024 WestJet · WS 6328 Depart at 7:50am from Toronto (YYZ) Fly for 2h 27m Arrive at 10:17am in Atlanta (ATL)

    Layover in Atlanta for 6h 46m

    Mon Dec 2nd 2024 WestJet · WS 7436 Depart at 5:03pm from Atlanta (ATL) Fly for 1h 51m Arrive at 5:54pm in Chicago (MDW)

  • US$846
    Caribbean AirlinesWestJetWestJet
    8:15am - 5:54pm
    Sun Dec 1st 2024
    35h 39m
    Port of Spain (POS) → Chicago (MDW)
    2 Stops

    Sun Dec 1st 2024 Caribbean Airlines · BW 610 Depart at 8:15am from Port of Spain (POS) Fly for 6h 5m Arrive at 1:20pm in Toronto (YYZ)

    Layover in Toronto for 4h 55m

    Sun Dec 1st 2024 WestJet · WS 6381 Depart at 6:15pm from Toronto (YYZ) Fly for 2h 26m Arrive at 8:41pm in Atlanta (ATL)

    Layover in Atlanta for 20h 22m

    Mon Dec 2nd 2024 WestJet · WS 7436 Depart at 5:03pm from Atlanta (ATL) Fly for 1h 51m Arrive at 5:54pm in Chicago (MDW)

  • US$896
    Copa AirlinesCopa AirlinesFrontier Airlines
    3:38am - 4:21pm
    Mon Dec 2nd 2024
    14h 43m
    Port of Spain (POS) → Chicago (MDW)
    2 Stops

    Mon Dec 2nd 2024 Copa Airlines · CM 315 Depart at 3:38am from Port of Spain (POS) Fly for 3h 16m Arrive at 5:54am in Panama (PTY)

    Layover in Panama for 2h 7m

    Mon Dec 2nd 2024 Copa Airlines · CM 226 Depart at 8:01am from Panama (PTY) Fly for 3h 9m Arrive at 11:10am in Miami (MIA)

    Layover in Miami for 2h 58m

    Mon Dec 2nd 2024 Frontier Airlines · F9 2109 Depart at 2:08pm from Miami (MIA) Fly for 3h 13m Arrive at 4:21pm in Chicago (MDW)

  • US$917
    Copa AirlinesCopa AirlinesFrontier Airlines
    3:38am - 5:58pm
    Sun Dec 1st 2024
    16h 20m
    Port of Spain (POS) → Chicago (MDW)
    2 Stops

    Sun Dec 1st 2024 Copa Airlines · CM 315 Depart at 3:38am from Port of Spain (POS) Fly for 3h 16m Arrive at 5:54am in Panama (PTY)

    Layover in Panama for 3h 31m

    Sun Dec 1st 2024 Copa Airlines · CM 880 Depart at 9:25am from Panama (PTY) Fly for 4h 24m Arrive at 1:49pm in Atlanta (ATL)

    Layover in Atlanta for 3h 11m

    Sun Dec 1st 2024 Frontier Airlines · F9 2779 Depart at 5:00pm from Atlanta (ATL) Fly for 1h 58m Arrive at 5:58pm in Chicago (MDW)

  • US$982
    Caribbean AirlinesWestJetWestJet
    8:15am - 9:50am
    Sun Dec 1st 2024
    27h 35m
    Port of Spain (POS) → Chicago (MDW)
    2 Stops

    Sun Dec 1st 2024 Caribbean Airlines · BW 610 Depart at 8:15am from Port of Spain (POS) Fly for 6h 5m Arrive at 1:20pm in Toronto (YYZ)

    Layover in Toronto for 4h 55m

    Sun Dec 1st 2024 WestJet · WS 6381 Depart at 6:15pm from Toronto (YYZ) Fly for 2h 26m Arrive at 8:41pm in Atlanta (ATL)

    Layover in Atlanta for 12h 9m

    Mon Dec 2nd 2024 WestJet · WS 7183 Depart at 8:50am from Atlanta (ATL) Fly for 2h 0m Arrive at 9:50am in Chicago (MDW)

  • US$1061
    Caribbean AirlinesFrontier AirlinesFrontier Airlines
    9:10am - 1:15am
    Sun Dec 1st 2024
    18h 5m
    Port of Spain (POS) → Chicago (MDW)
    2 Stops

    Sun Dec 1st 2024 Caribbean Airlines · BW 484 Depart at 9:10am from Port of Spain (POS) Fly for 4h 5m Arrive at 12:15pm in Miami (MIA)

    Layover in Miami for 2h 52m

    Sun Dec 1st 2024 Frontier Airlines · F9 2675 Depart at 3:07pm from Miami (MIA) Fly for 3h 31m Arrive at 5:38pm in Dallas (DFW)

    Layover in Dallas for 5h 21m

    Sun Dec 1st 2024 Frontier Airlines · F9 2882 Depart at 10:59pm from Dallas (DFW) Fly for 2h 16m Arrive at 1:15am in Chicago (MDW)

  • US$1226
    Caribbean AirlinesWestJetWestJet
    1:55am - 5:54pm
    Sun Dec 1st 2024
    17h 59m
    Port of Spain (POS) → Chicago (MDW)
    2 Stops

    Sun Dec 1st 2024 Caribbean Airlines · BW 602 Depart at 1:55am from Port of Spain (POS) Fly for 6h 5m Arrive at 7:00am in Toronto (YYZ)

    Layover in Toronto for 5h 21m

    Sun Dec 1st 2024 WestJet · WS 6342 Depart at 12:21pm from Toronto (YYZ) Fly for 2h 17m Arrive at 2:38pm in Atlanta (ATL)

    Layover in Atlanta for 2h 25m

    Sun Dec 1st 2024 WestJet · WS 6781 Depart at 5:03pm from Atlanta (ATL) Fly for 1h 51m Arrive at 5:54pm in Chicago (MDW)

@sarahbb1
Sarah Belizaire
@sarahbb1

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@eyupitsjohn
John Ford
@eyupitsjohn

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@oamingsonaa
Roaming Sonaa
@roamingsonaa

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@andy_travels
Andy Travels
@andy_travels

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@travelwitbender
Travel With Bender
@travelwitbender

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

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Flightlist Interviews 7 Travel Experts On Why They Book One Way Flights
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