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Cheap Flights from Chicago to Port of Spain, TT, Trinidad And Tobago - CHI to POS

Popular flights from Chicago to Port of Spain

We’ve got the inside scoop on finding the best time to fly for the best price. Not sure when to travel for your next vacation? Find details below on when-to-fly and when-to-buy.

American Airlines
Departure Date Return Date Lowest Price
Jun 2, 2016 Jun 8, 2016 $612
Jun 2, 2016 Jun 8, 2016 $612
Jun 3, 2016 Jun 10, 2016 $612
Jun 3, 2016 Jun 10, 2016 $612
Caribbean Airlines
Departure Date Return Date Lowest Price
May 22, 2016 May 28, 2016 $769
JetBlue Airways
Departure Date Return Date Lowest Price
Jun 2, 2016 Jun 9, 2016 $629
United Airlines
Departure Date Return Date Lowest Price
Aug 29, 2016 Sep 7, 2016 $583

How Much Does it Cost to Fly from Chicago to Port of Spain (CHI to POS)?

We have collected flight cost data from across the web for travel from Chicago to Port of Spain, and have found the average flight price for this trip to be $615.

When Can I Buy the Cheapest Flight from Chicago to Port of Spain (CHI to POS)?

Airlines can adjust prices for plane tickets from Chicago to Port of Spain based on the day and time that you decide to book your flight. We have collected data from all airlines, and have discovered that the best days to book flights are Tuesdays, Wednesdays, and Saturdays. Read our article to find more information about the best time to buy airline tickets.

Cheapest Day To Fly from Chicago to Port of Spain

The chart below shows up-to-date information regarding the cheapest days to fly from Chicago to Port of Spain.

Monday Tuesday Wednesday Thursday Friday Saturday Sunday
$629 $629 $609 $607 $612 $594 $626

Lowest Fares Chart By Month from Chicago to Port of Spain

The chart below shows the lowest fare by month when flying from Chicago to Port of Spain.

Month Origin Destination Carrier Depart Date Return Date Stops Price
May Chicago Port of Spain United 5/28/16 6/1/16 2 $594
June Chicago Port of Spain United 6/2/16 6/8/16 1 $607
July Chicago Port of Spain American 7/9/16 7/19/16 1 $615
August Chicago Port of Spain United 8/29/16 9/7/16 2 $583
September Chicago Port of Spain American 9/25/16 9/28/16 1 $639
October Chicago Port of Spain United 10/31/16 11/12/16 1 $629
November Chicago Port of Spain American 11/15/16 11/22/16 2 $615
December Chicago Port of Spain American 12/10/16 12/11/16 2 $612

Round Trip vs One Way Flights from Chicago to Port of Spain (CHI to POS)

We have found that there is often no price difference between buying a round trip flight versus a one way flight. Increased flexibility is the main benefit when it comes to buying a one way flight from Chicago to Port of Spain. However, booking a round trip flight can be a simpler process. You can compare round trip and one way flights by using our flight comparison.

The average price for one way flights from Chicago to Port of Spain is $308.

The average price for round trip flights from Chicago to Port of Spain is $656.

Chicago to Port of Spain Flight Questions

Below are some common questions that asked about this flight route:

Question: What are the most popular connecting cities when flying from Chicago to Port of Spain?
Answer: Houston, TX

Airlines Flying from Chicago to Port of Spain (CHI to POS)

Below are the different airlines that fly from Chicago to Port of Spain with the average price of their plane tickets. Just remember that different airlines offer different levels of comfort and service, so consider convenience when choosing your airline.

Below is the full flight schedule summary of the next 30 days for flights from Chicago to Port of Spain.

Chicago to Port of Spain
Airline Connections Mon Tue Wed Thu Fri Sat Sun
American MIA X X X X X X X
American MCO / MIA X X X X X X X
JetBlue JFK X X X X X X X
Copa PTY X X X X X X
United IAH X X X X X X X

Airports for Your Route

These pages contain information about the major airports in Chicago and Port of Spain, so you can feel comfortable knowing how to get around whether you are about to take off or you just landed.

Cheap Domestic Flights from Chicago - CHI

FlightsAirlineLowest Price
Chicago to Miami American, Alaska, Frontier, United $108
Chicago to San Juan Silver, American, Alaska, JetBlue, Frontier, Spirit, United $215
Chicago to Dallas - Ft Worth American, Alaska, Frontier, Spirit, United $79
Chicago to Atlanta American, Spirit, United $71
Chicago to Washington American, Alaska, Frontier, United $88
Chicago to San Francisco American, Alaska, Frontier, United, Virgin America $186
Chicago to Denver American, Alaska, Frontier, Spirit, United $81
Chicago to Boston American, JetBlue, Spirit, United $79
Chicago to Houston American, Spirit, United $116
Chicago to Phoenix American, Alaska, Frontier, Spirit, United $176
Chicago to Ft Lauderdale American, Alaska, JetBlue, Spirit, United $134
Chicago to Tampa American, Alaska, Spirit, United $137
Chicago to Minneapolis - St Paul American, Frontier, Spirit, United $65
Chicago to Seattle American, Alaska, Frontier, Spirit, United, Virgin America $194
Chicago to Newark American, Alaska, JetBlue, United $195

Cheap International Flights from Chicago - CHI

FlightsAirlineLowest Price
Chicago to Tobago American, Caribbean, United $906
Chicago to Grenada American, JetBlue, United $772
Chicago to Barbados American, Alaska, JetBlue, United $472
Chicago to St Lucia American, JetBlue, United $575
Chicago to London American, Air Berlin, Air France, Alaska, Finnair, Alitalia, JetBlue, British Airways, BMI, Condor, Aer Lingus, Iberia, Meridiana, KLM, Lufthansa, LOT, Thomas Cook, Czech, Arkefly, Austrian, SAS, Brussels, Tap Portugal, United, Air Europa, Virgin Atlantic $849
Chicago to Punta Cana American, JetBlue, Frontier, Spirit, United, Great Lakes $331
Chicago to St Thomas Island American, JetBlue, Spirit, United $321
Chicago to Toronto Air Choice One, American, Air Canada, Alaska, JetBlue, Frontier, Spirit, Public Charters, Porter, United, WestJet, Great Lakes $225
Chicago to St Maarten American, Alaska, JetBlue, Spirit, United $425
Chicago to Cancun Silver, Interjet, American, AeroMexico, Alaska, JetBlue, Frontier, Spirit, Sun Country, United, Virgin America, Volaris, Great Lakes $281
Chicago to Aruba Insel Air Aruba, American, JetBlue, Spirit, United $393

Cheap International Flights to Port of Spain - POS

FlightsAirlineLowest Price
Indianapolis to Port of Spain American, JetBlue, Caribbean, United $681
Milwaukee to Port of Spain American, Caribbean, United Check Dates
Grand Rapids to Port of Spain American, United $837
Madison to Port of Spain American, Caribbean, United Check Dates
Cheap Flights from Chicago to Port of Spain, TT, Trinidad And Tobago, from $583 Round trip from CHI to POS