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$317+ 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 5/22. Fares are subject to change and may not be available on all flights or dates of travel.
POS — CHI
Jun 4 — Jun 111
Thu 6/4
Thu 6/11
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 May 5, 2026.

This Mytrip deal was found by Cheapflights users on 5/2. 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.
Fri 6/51:25 am
POS
-
ORD
1 stop14h 30m
Air Canada
Fri 6/129:55 am
ORD
-
POS
1 stop13h 20m
Air Canada
Deal found 5/2$582
This Priceline deal was found by Cheapflights users on 5/1. 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.
Mon 6/151:25 am
POS
-
ORD
2 stops18h 27m
Multiple Airlines
Tue 6/236:27 pm
ORD
-
POS
1 stop17h 59m
Multiple Airlines
Deal found 5/1$609
This Priceline deal was found by Cheapflights users on 5/1. 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 6/141:25 am
POS
-
ORD
1 stop12h 56m
Air Canada
Mon 6/222:15 pm
ORD
-
POS
1 stop9h 00m
Air Canada
Deal found 5/1$616
This Priceline deal was found by Cheapflights users on 5/3. 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.
Wed 8/261:25 am
POS
-
ORD
2 stops18h 21m
Air Canada
Mon 8/318:45 am
ORD
-
POS
2 stops14h 30m
Air Canada
Deal found 5/3$619
This Priceline deal was found by Cheapflights users on 4/30. 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.
Fri 5/221:25 am
POS
-
ORD
2 stops18h 27m
Air Canada
Tue 6/308:40 pm
ORD
-
POS
1 stop26h 35m
Air Canada
Deal found 4/30$646
This Expedia deal was found by Cheapflights users on 5/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/251:25 am
POS
-
ORD
1 stop13h 00m
Multiple Airlines
Wed 6/33:27 pm
ORD
-
POS
1 stop21h 54m
Multiple Airlines
Deal found 5/1$663
This Air Canada deal was found by Cheapflights users on 5/3. 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 7/221:25 am
POS
-
ORD
1 stop12h 57m
Air Canada
Sun 7/269:50 am
ORD
-
POS
1 stop13h 25m
Air Canada
Deal found 5/3$665
This Air Canada deal was found by Cheapflights users on 5/3. 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 7/221:25 am
POS
-
ORD
1 stop12h 57m
Air Canada
Mon 7/278:45 am
ORD
-
POS
2 stops14h 30m
Air Canada
Deal found 5/3$668
This Mytrip deal was found by Cheapflights users on 5/1. 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.
Fri 5/221:25 am
POS
-
ORD
3 stops31h 57m
Multiple Airlines
Tue 6/305:35 pm
ORD
-
POS
1 stop29h 40m
Multiple Airlines
Deal found 5/1$674

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 May 5, 2026.

Round-trip from

$582
(Priceline)

One-way from

$317
(Kiwi.com)
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 May 5, 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 6/5

1:25 am-6:52 pm

2 stops18h 27m

Chicago O'Hare Intl

Fri 6/12

9:55 am-12:15 am

1 stop13h 20m

$582

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 6/14

1:25 am-2:50 pm

2 stops14h 25m

Chicago O'Hare Intl

Mon 6/22

8:35 am-12:15 am

2 stops14h 40m

$623

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 7/22

1:25 am-1:22 pm

1 stop12h 57m

Chicago O'Hare Intl

Mon 7/27

8:45 am-12:15 am

2 stops14h 30m

$668

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 7/22

1:25 am-1:22 pm

1 stop12h 57m

Chicago O'Hare Intl

Sun 7/26

8:45 am-12:15 am

2 stops14h 30m

$668

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 6/14

1:25 am-6:36 pm

2 stops18h 11m

Chicago O'Hare Intl

Mon 6/22

6:00 am-12:15 am

3 stops17h 15m

$681

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Mon 5/25

1:25 am-1:25 pm

1 stop13h 00m

Chicago O'Hare Intl

Wed 7/1

9:50 am-12:25 am

1 stop13h 35m

$686

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 6/5

1:25 am-6:52 pm

2 stops18h 27m

Chicago O'Hare Intl

Fri 6/12

8:20 pm-6:35 pm

2 stops21h 15m

$687

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 6/19

7:45 pm-8:45 am

1 stop14h 00m

Chicago O'Hare Intl

Wed 6/24

6:27 pm-1:35 pm

1 stop18h 08m

$688
Quickest round-trip

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 6/19

3:13 pm-11:30 pm

1 stop9h 17m

Chicago O'Hare Intl

Wed 6/24

6:59 am-11:00 pm

1 stop15h 01m

$690

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 5/31

12:30 am-10:20 am

1 stop10h 50m

Chicago O'Hare Intl

Sun 6/7

9:36 pm-11:23 pm

1 stop24h 47m

$693

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/2

Showing 1-10 of 22 resultsSorted by cheapest first
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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, June is the cheapest month in which you can book a flight from Trinidad and Tobago to Chicago (average of $299). Flying from Trinidad and Tobago to Chicago in April is currently the most expensive (average of $913). 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 fly from Trinidad and Tobago to Chicago in about 18h 27m. The time it takes to get you to your destination can typically vary by up to . The distance between Trinidad and Tobago and Chicago is about 2697 mi.

  • 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, June is the cheapest month in which you can book a flight from Trinidad and Tobago to Chicago (average of $299). Flying from Trinidad and Tobago to Chicago in April is currently the most expensive (average of $913). 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
Benton Harbor
Lansing
Merrillville
Hammond
Porter

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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 May 5, 2026.
AirlineCheapestAverageFlexibilityOn-time
Copa AirlinesCheapest$299Average$563FlexibilityNo cancel feeOn-time70%
Air CanadaCheapest$322Average$506FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$572Average$720FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$573Average$790FlexibilityNo cancel feeOn-time71%

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