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$348+ Cheap flights from Trinidad and Tobago to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/9. Fares are subject to change and may not be available on all flights or dates of travel.
POS — CHI
Jul 16 — Jul 231
Thu 7/16
Thu 7/23
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 June 16, 2026.

This Kiwi.com deal was found by Cheapflights users on 6/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/2710:10 am
POS
-
ORD
1 stop27h 05m
Multiple Airlines
Mon 8/38:05 am
ORD
-
POS
1 stop10h 55m
Multiple Airlines
Deal found 6/12$597
This Priceline deal was found by Cheapflights users on 6/12. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/211:25 am
POS
-
ORD
2 stops18h 27m
Air Canada
Mon 7/62:15 pm
ORD
-
POS
1 stop9h 00m
Air Canada
Deal found 6/12$601
This Air Canada deal was found by Cheapflights users on 6/15. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/101:25 am
POS
-
ORD
1 stop14h 30m
Air Canada
Sat 8/296:21 pm
ORD
-
POS
2 stops28h 54m
Air Canada
Deal found 6/15$630
This Air Canada deal was found by Cheapflights users on 6/15. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/81:25 am
POS
-
ORD
2 stops34h 55m
Air Canada
Sat 8/298:40 pm
ORD
-
POS
1 stop26h 35m
Air Canada
Deal found 6/15$633
This Air Canada deal was found by Cheapflights users on 6/15. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/81:25 am
POS
-
ORD
2 stops34h 55m
Air Canada
Fri 8/288:45 am
ORD
-
POS
2 stops14h 30m
Air Canada
Deal found 6/15$636
This Mytrip deal was found by Cheapflights users on 6/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/151:25 am
POS
-
ORD
1 stop12h 57m
Air Canada
Tue 7/213:50 pm
ORD
-
POS
1 stop31h 25m
Air Canada
Deal found 6/15$659
This FlightHub deal was found by Cheapflights users on 6/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/31:25 am
POS
-
ORD
2 stops18h 22m
Air Canada
Thu 7/92:08 pm
ORD
-
POS
2 stops33h 07m
Air Canada
Deal found 6/12$663
This Air Canada deal was found by Cheapflights users on 6/12. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/81:25 am
POS
-
ORD
1 stop12h 57m
Air Canada
Wed 7/229:50 am
ORD
-
POS
1 stop13h 25m
Air Canada
Deal found 6/12$676

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 June 16, 2026.

Round-trip from

$597
(Kiwi.com)

One-way from

$348
(Expedia)
From Trinidad and Tobago to Chicago (CHI)
Search Deals
One-way flight 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 June 16, 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

Fri 7/3

1:25 am-6:47 pm

2 stops18h 22m

Chicago O'Hare Intl

Thu 7/9

2:08 pm-12:15 am

2 stops33h 07m

$663
Quickest round-trip

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 7/8

1:25 am-1:22 pm

1 stop12h 57m

Chicago O'Hare Intl

Wed 7/22

9:50 am-12:15 am

1 stop13h 25m

$676

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sat 7/4

2:19 pm-1:57 pm

1 stop24h 38m

Chicago O'Hare Intl

Thu 7/9

8:02 am-1:16 pm

1 stop28h 14m

$680

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 7/28

3:50 am-4:00 am

1 stop25h 10m

Chicago O'Hare Intl

Wed 8/5

3:21 pm-1:47 am

1 stop9h 26m

$680

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 7/22

3:50 am-4:00 am

1 stop25h 10m

Chicago O'Hare Intl

Sun 7/26

3:21 pm-1:16 pm

1 stop20h 55m

$680

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 9/6

2:00 am-2:47 pm

1 stop13h 47m

Chicago O'Hare Intl

Tue 9/15

8:50 am-11:23 pm

1 stop13h 33m

$690
Cheapest one-way
Quickest one-way

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 8/9

1:25 am-1:22 pm

1 stop12h 57m

$348

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Mon 8/10

9:10 am-4:00 pm

2 stops31h 50m

$402

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/13

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
No data available for this route at this time. Please check back soon.

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 18h 22m. The time it takes to get you to your destination can typically vary by up to 6h 16m. 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.

See more FAQs

Traveling to a place near Chicago?

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

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Top 2 airlines flying from Trinidad and Tobago to Chicago

Discover the top 2 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 June 16, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$572Average$720FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$573Average$799FlexibilityNo cancel feeOn-time71%

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