HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$252+ Cheap flights from Trinidad 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 5/8. Fares are subject to change and may not be available on all flights or dates of travel.
POS — CHI
Apr 24 — May 11
Fri 4/24
Fri 5/1
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Trinidad to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Trinidad to Chicago

Cheapest flights from Trinidad to Chicago
Explore the most affordable flight options available from Trinidad to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 25, 2026.

This Copa Airlines deal was found by Cheapflights users on 3/23. 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 4/263:05 pm
ORD
-
POS
1 stop9h 35m
Copa Airlines
Deal found 3/23$417
This Air Canada deal was found by Cheapflights users on 3/24. 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 4/269:05 am
ORD
-
POS
1 stop14h 15m
Air Canada
Deal found 3/24$448
This Kiwi.com deal was found by Cheapflights users on 3/22. 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.
Wed 5/69:10 am
POS
-
ORD
1 stop25h 27m
Multiple Airlines
Wed 5/1311:51 am
ORD
-
POS
2 stops30h 04m
Multiple Airlines
Deal found 3/22$484
This Copa Airlines deal was found by Cheapflights users on 3/22. 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
Wed 5/138:02 am
ORD
-
POS
1 stop16h 44m
Copa Airlines
Deal found 3/22$492
This Kiwi.com deal was found by Cheapflights users on 3/23. 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 5/79:10 am
POS
-
ORD
2 stops26h 36m
Multiple Airlines
Thu 5/147:45 pm
ORD
-
POS
1 stop23h 15m
Multiple Airlines
Deal found 3/23$499
This Kiwi.com deal was found by Cheapflights users on 3/24. 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.
Sat 5/99:10 am
POS
-
ORD
1 stop25h 27m
Multiple Airlines
Sat 5/166:40 am
ORD
-
POS
1 stop11h 15m
Multiple Airlines
Deal found 3/24$514
This Kiwi.com deal was found by Cheapflights users on 3/22. 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 6/1110:10 am
POS
-
ORD
1 stop15h 17m
Multiple Airlines
Mon 6/157:55 am
ORD
-
POS
1 stop11h 05m
Multiple Airlines
Deal found 3/22$562
This Copa Airlines deal was found by Cheapflights users on 3/20. 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 5/62:22 pm
POS
-
ORD
1 stop11h 53m
Copa Airlines
Sun 5/108:02 am
ORD
-
POS
1 stop16h 44m
Copa Airlines
Deal found 3/20$566

Find flight deals from Trinidad to Chicago

Keep the following information in mind while searching for Trinidad to Chicago flight deals. Data was last updated March 25, 2026.

Round-trip from

$417
(Copa Airlines)

One-way from

$252
(Trip.com)
From Trinidad to Chicago (CHI)
Search Deals
One-way flight from Trinidad to Chicago (CHI)
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Trinidad 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 25, 2026.
Use the filters below to find and compare flights from Trinidad 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 4/17

2:17 pm-1:13 am

1 stop11h 56m

Chicago O'Hare Intl

Sun 4/26

3:05 pm-1:40 am

1 stop9h 35m

$417
Quickest round-trip

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 5/6

2:22 pm-1:15 am

1 stop11h 53m

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

Mon 5/4

3:49 am-2:06 pm

1 stop11h 17m

Chicago O'Hare Intl

Tue 5/12

8:02 am-1:46 am

1 stop16h 44m

$492

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sat 5/9

9:10 am-9:37 am

1 stop25h 27m

Chicago O'Hare Intl

Sat 5/16

6:40 am-6:55 pm

1 stop11h 15m

$514

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Mon 5/4

1:25 am-6:58 pm

2 stops18h 33m

Chicago O'Hare Intl

Tue 5/12

9:49 am-1:36 pm

2 stops26h 47m

$615

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Mon 8/3

2:19 pm-1:02 am

1 stop11h 43m

Chicago O'Hare Intl

Sat 8/8

8:02 am-1:47 am

1 stop16h 45m

$678

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 5/6

2:45 pm-8:51 am

2 stops19h 06m

Chicago O'Hare Intl

Sun 5/10

6:00 am-1:35 pm

2 stops30h 35m

$680

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 6/18

12:30 am-8:00 am

1 stop32h 30m

Chicago O'Hare Intl

Mon 6/22

6:30 am-11:23 pm

1 stop15h 53m

$712

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 7/9

12:30 am-11:15 pm

1 stop23h 45m

Chicago O'Hare Intl

Mon 7/13

7:35 am-11:23 pm

1 stop14h 48m

$713
Cheapest one-way

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 5/8

10:10 am-11:59 pm

1 stop14h 49m

$252

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/24

Showing 1-10 of 16 resultsSorted by cheapest first
1
2

Best time to book a flight from Trinidad to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Trinidad 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 to Chicago

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

Currently, December is the cheapest month in which you can book a flight from Trinidad to Chicago (average of $304). Flying from Trinidad 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 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 to Chicago?

    Departing from Trinidad to Chicago will take you 11h 56m. The distance between Trinidad and Chicago is about 2697 mi.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Trinidad 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 to Chicago?

    Currently, December is the cheapest month in which you can book a flight from Trinidad to Chicago (average of $304). Flying from Trinidad 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Top 4 airlines flying from Trinidad to Chicago

Discover the top 4 airlines that operate flights from Trinidad 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 25, 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%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.