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$417+ Cheap flights from Trinidad and Tobago to Chicago (CHI)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/17. Fares are subject to change and may not be available on all flights or dates of travel.
POS — CHI
Apr 16 — Apr 231
Thu 4/16
Thu 4/23
1 adult, Economy
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Cheap flight deals from Trinidad and Tobago to Chicago

Cheapest flights from Trinidad and Tobago to Chicago
Explore the most affordable flight options available from Trinidad and Tobago to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 17, 2026.

This Copa Airlines deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/172:17 pm
POS
-
ORD
1 stop11h 56m
Copa Airlines
Sun 4/268:06 am
ORD
-
POS
1 stop16h 34m
Copa Airlines
Deal found 3/15$417
This Air Canada deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/161:20 am
POS
-
ORD
1 stop12h 45m
Air Canada
Sun 4/268:40 am
ORD
-
POS
2 stops14h 40m
Air Canada
Deal found 3/16$423
This Priceline deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/91:20 am
POS
-
ORD
2 stops18h 38m
Air Canada
Sun 4/122:00 pm
ORD
-
POS
1 stop9h 20m
Air Canada
Deal found 3/13$443
This Copa Airlines deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/292:17 pm
POS
-
ORD
1 stop11h 56m
Copa Airlines
Wed 5/63:21 pm
ORD
-
POS
1 stop9h 25m
Copa Airlines
Deal found 3/14$455
This Copa Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/53:49 am
POS
-
ORD
1 stop11h 17m
Copa Airlines
Sun 5/103:21 pm
ORD
-
POS
1 stop9h 25m
Copa Airlines
Deal found 3/12$492
This Priceline deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/281:20 am
POS
-
ORD
1 stop12h 45m
Multiple Airlines
Wed 5/69:41 am
ORD
-
POS
2 stops26h 54m
Multiple Airlines
Deal found 3/14$505
This Priceline deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/281:20 am
POS
-
ORD
2 stops18h 38m
Air Canada
Wed 5/69:55 am
ORD
-
POS
1 stop13h 20m
Air Canada
Deal found 3/14$507
This Kiwi.com deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/309:10 am
POS
-
ORD
1 stop15h 49m
Multiple Airlines
Thu 5/711:51 am
ORD
-
POS
2 stops30h 04m
Multiple Airlines
Deal found 3/16$542

Find flight deals from Trinidad and Tobago to Chicago

Keep the following information in mind while searching for Trinidad and Tobago to Chicago flight deals. Data was last updated March 17, 2026.

Round-trip from

$417
(Copa Airlines)
From Trinidad and Tobago to Chicago (CHI)
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Trinidad and Tobago to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 17, 2026.
Use the filters below to find and compare flights from Trinidad and Tobago to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 4/16

1:20 am-1:05 pm

1 stop12h 45m

Chicago O'Hare Intl

Sun 4/26

9:05 am-12:20 am

1 stop14h 15m

$425

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 4/9

1:20 am-6:58 pm

2 stops18h 38m

Chicago O'Hare Intl

Sun 4/12

2:00 pm-12:20 am

1 stop9h 20m

$443

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 4/29

2:17 pm-1:13 am

1 stop11h 56m

Chicago O'Hare Intl

Wed 5/6

3:21 pm-1:46 am

1 stop9h 25m

$455
Quickest round-trip

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 5/5

3:49 am-2:06 pm

1 stop11h 17m

Chicago O'Hare Intl

Sun 5/10

3:21 pm-1:46 am

1 stop9h 25m

$492

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 4/28

1:20 am-1:05 pm

1 stop12h 45m

Chicago O'Hare Intl

Wed 5/6

9:41 am-1:35 pm

2 stops26h 54m

$505

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 4/28

1:20 am-6:58 pm

2 stops18h 38m

Chicago O'Hare Intl

Wed 5/6

9:55 am-12:15 am

1 stop13h 20m

$507

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 4/30

9:10 am-11:59 pm

1 stop15h 49m

Chicago O'Hare Intl

Thu 5/7

3:05 pm-8:00 pm

1 stop27h 55m

$547

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 4/26

9:10 am-1:05 pm

1 stop28h 55m

Chicago O'Hare Intl

Sun 5/3

3:52 pm-6:55 pm

1 stop26h 03m

$567

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 8/2

2:19 pm-1:02 am

1 stop11h 43m

Chicago O'Hare Intl

Thu 8/6

1:20 am-1:17 pm

1 stop10h 57m

$586
Cheapest one-way
Quickest one-way

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 4/12

9:10 am-9:50 am

1 stop25h 40m

$439

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/16

Sorted by cheapest first

Best time to book a flight from Trinidad and Tobago to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Trinidad and Tobago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Trinidad and Tobago to Chicago

What is the cheapest month to book a flight from Trinidad and Tobago to Chicago?

Currently, December is the cheapest month in which you can book a flight from Trinidad and Tobago to Chicago (average of $304). Flying from Trinidad and Tobago to Chicago in April is currently the most expensive (average of $998). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Related info for your journey

Find useful and relevant information for your journey from Trinidad and Tobago to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Trinidad and Tobago to Chicago?

    Airlines like Air Canada and Copa Airlines fly from Trinidad and Tobago to Chicago in about 11h 56m. The time it takes to get you to your destination can typically vary by up to 49m. The distance between Trinidad and Tobago and Chicago is about 2697 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • Can I find deals for flights from Trinidad and Tobago to Chicago that include hotel bookings?

    Yes. In addition to deals on Trinidad and Tobago to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Trinidad and Tobago to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Trinidad and Tobago to Chicago.

  • Can I find deals for business class flights from Trinidad and Tobago to Chicago?

    Yes. Cheapflights offers flight deals from Trinidad and Tobago to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Trinidad and Tobago to Chicago?

    Currently, December is the cheapest month in which you can book a flight from Trinidad and Tobago to Chicago (average of $304). Flying from Trinidad and Tobago to Chicago in April is currently the most expensive (average of $998). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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Top 4 airlines flying from Trinidad and Tobago to Chicago

Discover the top 4 airlines that operate flights from Trinidad and Tobago to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated March 17, 2026.
AirlineCheapestAverageFlexibilityOn-time
Copa AirlinesCheapest$299Average$374FlexibilityNo cancel feeOn-time70%
Air CanadaCheapest$322Average$506FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$559Average$792FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$562Average$790FlexibilityNo cancel feeOn-time71%

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