Fare Guide

Estimated lowest fares found within 7 days

Cheapest Airline United Airlines
Cheapest Month July
Cheapest Day of the Week Tuesday
Cheapest Airline United Airlines

The cheapest airline(s) flying from Chicago to Port-of-Spain is United Airlines.

  • United Airlines United Airlines
  • American Airlines American Airlines
  • Copa Airlines Copa Airlines
  • JetBlue Airways JetBlue Airways
Cheapest Month July

Travel Period: June 2025 - May 2026

The cheapest month(s) to fly from Chicago to Port-of-Spain is July.

  • Jun 2025
  • Jul 2025
  • Aug 2025
  • Sep 2025
  • Oct 2025
  • Nov 2025
  • Dec 2025
  • Jan 2026
  • Feb 2026
  • Mar 2026
  • Apr 2026
  • May 2026
Cheapest Day of the Week Tuesday

The cheapest day(s) of the week to fly from Chicago to Port-of-Spain is Tuesday.

  • Sun Sunday
  • Mon Monday
  • Tue Tuesday
  • Wed Wednesday
  • Thu Thursday
  • Fri Friday
  • Sat Saturday

Flight Schedules

Last Updated: Fri, 2 May, 2025

  • Time Earliest
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      • Availability
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      • 05:00 ORD
        14:05 POS
        8Hrs, 05m 1 Stop (MIA)
      • ORDChicago O'Hare International Airport 05:00 - POS 14:05 8h 05m 1 Stop (MIA) Miami
      • ORDChicago O'Hare International Airport 05:00
        MIAMiami International Airport 10:15
      • MIAMiami International Airport 09:09
        POSPort of Spain Airport 14:05
      • 8h 05m (1h 06m)
      • 1 Stop MIA · Miami 1h 06m
      • American Airlines (AA 2984)Boeing 737 800
        American Airlines (AA 2703)Boeing 737 Max 8 Passenger
      • American Airlines (AA 2984)
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        • S
      • 05:00 ORD
        14:15 POS
        8Hrs, 15m 1 Stop (MIA)
      • ORDChicago O'Hare International Airport 05:00 - POS 14:15 8h 15m 1 Stop (MIA) Miami
      • ORDChicago O'Hare International Airport 05:00
        MIAMiami International Airport 10:15
      • MIAMiami International Airport 09:09
        POSPort of Spain Airport 14:15
      • 8h 15m (1h 06m)
      • 1 Stop MIA · Miami 1h 06m
      • American Airlines (AA 2984)Boeing 737 800
        American Airlines (AA 2703)Boeing 737 Max 8 Passenger
      • American Airlines (AA 2984)
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      • 10:40 ORD
        23:23 POS
        11Hrs, 43m 1 Stop (IAH)
      • ORDChicago O'Hare International Airport 10:40 - POS 23:23 11h 43m 1 Stop (IAH) Houston
      • ORDChicago O'Hare International Airport 10:40
        IAHHouston George Bush Intercontinental Airport 16:48
      • IAHHouston George Bush Intercontinental Airport 13:40
        POSPort of Spain Airport 23:23
      • 11h 43m (3h 08m)
      • 1 Stop IAH · Houston 3h 08m
      • United Airlines (UA 2483)Boeing 737 Max 9 Passenger
        United Airlines (UA 2353)Boeing 737 Max 8 Passenger
      • United Airlines (UA 2483)
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      • 19:45 YYZ
        15:24 PIT
        11Hrs, 40m 1 Stop (POS)
      • YYZToronto Lester B Pearson Intl Airport 19:45 - PIT 15:24 11h 40m 1 Stop (POS) Port-of-Spain
      • YYZToronto Lester B Pearson Intl Airport 19:45
        ORDChicago O'Hare International Airport 12:45
      • POSPort of Spain Airport 01:25
        PITPittsburgh International Airport 15:24
      • 11h 40m (3h 11m)
      • 1 Stop POS · Port-of-Spain 3h 11m
      • Air Canada (AC 984)Boeing 737 Max 8 Passenger
        United Airlines (UA 3655)Embraer 175
      • Air Canada (AC 984)
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      • 12:47 ORD
        23:23 POS
        9Hrs, 36m 1 Stop (IAH)
      • ORDChicago O'Hare International Airport 12:47 - POS 23:23 9h 36m 1 Stop (IAH) Houston
      • ORDChicago O'Hare International Airport 12:47
        IAHHouston George Bush Intercontinental Airport 16:48
      • IAHHouston George Bush Intercontinental Airport 15:47
        POSPort of Spain Airport 23:23
      • 9h 36m (1h 01m)
      • 1 Stop IAH · Houston 1h 01m
      • United Airlines (UA 2657)Boeing 737 Max 9 Passenger
        United Airlines (UA 2353)Boeing 737 Max 8 Passenger
      • United Airlines (UA 2657)
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      • 19:45 YYZ
        15:20 DTW
        11Hrs, 35m 1 Stop (POS)
      • YYZToronto Lester B Pearson Intl Airport 19:45 - DTW 15:20 11h 35m 1 Stop (POS) Port-of-Spain
      • YYZToronto Lester B Pearson Intl Airport 19:45
        ORDChicago O'Hare International Airport 12:50
      • POSPort of Spain Airport 01:25
        DTWDetroit Wayne County 15:20
      • 11h 35m (3h 15m)
      • 1 Stop POS · Port-of-Spain 3h 15m
      • Air Canada (AC 984)Boeing 737 Max 8 Passenger
        United Airlines (UA 3516)Embraer 175
      • Air Canada (AC 984)
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      • 13:00 ORD
        01:25 POS
        11Hrs, 25m 1 Stop (YYZ)
      • ORDChicago O'Hare International Airport 13:00 - POS 01:25 11h 25m 1 Stop (YYZ) Toronto
      • ORDChicago O'Hare International Airport 13:00
        YYZToronto Lester B Pearson Intl Airport 19:45
      • YYZToronto Lester B Pearson Intl Airport 15:46
        POSPort of Spain Airport 01:25
      • 11h 25m (3h 59m)
      • 1 Stop YYZ · Toronto 3h 59m
      • United Airlines (UA 2144)Airbus
        Air Canada (AC 984)Boeing 737 Max 8 Passenger
      • United Airlines (UA 2144)
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      • 14:00 ORD
        01:25 POS
        10Hrs, 25m 1 Stop (YYZ)
      • ORDChicago O'Hare International Airport 14:00 - POS 01:25 10h 25m 1 Stop (YYZ) Toronto
      • ORDChicago O'Hare International Airport 14:00
        YYZToronto Lester B Pearson Intl Airport 19:45
      • YYZToronto Lester B Pearson Intl Airport 16:42
        POSPort of Spain Airport 01:25
      • 10h 25m (3h 03m)
      • 1 Stop YYZ · Toronto 3h 03m
      • Air Canada (AC 506)Airbus A220 300
        Air Canada (AC 984)Boeing 737 Max 8 Passenger
      • Air Canada (AC 506)
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      • 15:07 ORD
        01:47 POS
        9Hrs, 40m 1 Stop (PTY)
      • ORDChicago O'Hare International Airport 15:07 - POS 01:47 9h 40m 1 Stop (PTY) Panama City
      • ORDChicago O'Hare International Airport 15:07
        PTYPanama City Tocumen International Airport 21:41
      • PTYPanama City Tocumen International Airport 20:35
        POSPort of Spain Airport 01:47
      • 9h 40m (1h 06m)
      • 1 Stop PTY · Panama City 1h 06m
      • Copa Airlines (CM 229)Boeing 737 800
        Copa Airlines (CM 314)Boeing 737 800
      • Copa Airlines (CM 229)
        • M
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      How far is Port-of-Spain from Chicago?

      The flight distance between Chicago and Port-of-Spain is 4304km. Check all available flights on Wego.

      When is the earliest and latest flight of the day?

      The earliest flight of the day departs at 05:00. The last flight of the day departs at 05:00. See the full list of flight times on Wego.

      All Airports in Port-of-Spain

      Port of Spain Airport POS

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