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$482+ Cheap flights from Trinidad and Tobago to Illinois

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 3/13. Fares are subject to change and may not be available on all flights or dates of travel.
POS — ORD
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap flight deals from Trinidad and Tobago to Illinois

Cheapest flights from Trinidad and Tobago to Illinois
Explore the most affordable flight options available from Trinidad and Tobago to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 29, 2026.

This Priceline deal was found by Cheapflights users on 1/28. 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 3/131:20 am
POS
-
ORD
1 stop12h 41m
Air Canada
Sat 3/218:40 pm
ORD
-
POS
1 stop26h 40m
Air Canada
Deal found 1/28$482
This Copa Airlines deal was found by Cheapflights users on 1/27. 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 5/108:02 am
ORD
-
POS
1 stop16h 44m
Copa Airlines
Deal found 1/27$574
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 7/159:10 am
POS
-
ORD
1 stop10h 05m
Multiple Airlines
Mon 7/206:34 pm
ORD
-
POS
1 stop23h 21m
Multiple Airlines
Deal found 1/28$587
This American Airlines deal was found by Cheapflights users on 1/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/63:47 pm
POS
-
ORD
2 stops19h 27m
American Airlines
Sun 5/106:58 pm
ORD
-
POS
1 stop18h 34m
American Airlines
Deal found 1/27$663
This Gotogate deal was found by Cheapflights users on 1/28. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/131:20 am
POS
-
ORD
1 stop12h 41m
Multiple Airlines
Sat 3/218:40 pm
ORD
-
POS
3 stops21h 55m
Multiple Airlines
Deal found 1/28$671
This American Airlines deal was found by Cheapflights users on 1/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/157:00 am
POS
-
ORD
2 stops12h 55m
American Airlines
Mon 7/207:50 am
ORD
-
POS
2 stops13h 57m
American Airlines
Deal found 1/28$708

Find flight deals from Trinidad and Tobago to Illinois

Keep the following information in mind while searching for Trinidad and Tobago to Illinois flight deals. Data was last updated January 29, 2026.

Round-trip from

$482
(Priceline)
From Trinidad and Tobago to Illinois
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Trinidad and Tobago to Illinois 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 January 29, 2026.
Use the filters below to find and compare flights from Trinidad and Tobago to Illinois that are best for you.

Fly from

Trinidad and Tobago

Fly to

Illinois

Route

Depart

Return

Price

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 3/13

1:20 am-1:01 pm

1 stop12h 41m

Chicago O'Hare Intl

Sat 3/21

8:40 pm-12:20 am

1 stop26h 40m

$482

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

8:02 am-1:46 am

1 stop16h 44m

$574

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 7/15

9:10 am-6:15 pm

1 stop10h 05m

Chicago O'Hare Intl

Mon 7/20

6:34 pm-6:55 pm

1 stop23h 21m

$587

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 5/6

3:47 pm-8:47 am

2 stops18h 00m

Chicago O'Hare Intl

Sun 5/10

8:44 pm-2:32 pm

2 stops16h 48m

$663

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 7/15

7:00 am-6:55 pm

2 stops12h 55m

Chicago O'Hare Intl

Mon 7/20

7:50 am-10:47 pm

2 stops13h 57m

$708

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 3/13

1:20 am-6:52 pm

2 stops18h 32m

Chicago O'Hare Intl

Sat 3/21

8:40 pm-7:35 pm

3 stops21h 55m

$800

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 2/25

2:20 am-11:38 am

1 stop11h 18m

$564

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 2/24

1:30 am-10:07 am

1 stop10h 37m

$733

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Mon 2/23

1:30 am-7:53 pm

1 stop20h 23m

$733

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 2/22

1:30 am-7:53 pm

1 stop20h 23m

$733

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 17 results
1
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Best time to book a flight from Trinidad and Tobago to Illinois

Have a flexible travel schedule? Discover the best time to fly to Illinois 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 Illinois

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

Currently, December is the cheapest month in which you can book a flight from Trinidad and Tobago to Illinois (average of $304). Flying from Trinidad and Tobago to Illinois in April is currently the most expensive (average of $632). 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.

Reviews of airlines servicing Illinois

Get insights into the airlines that provide service to Illinois. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Illinois. Reviews last updated January 29, 2026.
Read through reviews of airlines operating flights from Trinidad and Tobago to Illinois, such as Copa Airlines, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Copa Airlines
7.5
Good
1,560 reviews

Food

6.8

Boarding

7.8

Comfort

7.4

Overall

7.5

Crew

8.1

Entertainment

6.8

Reviews

1 / 20
2.0
Mediocre

Juan,Dec 2025

EZE - PTY

The outbound flight from Boston was awful. The handicapped services were the worst i have ever seen. NEVER AGAIN. THIS WAS NOT WORTH ANYWHERE NEAR $4K.
Copa Airlines
7.5
Good
1,560 reviews
Copa Airlines
7.5
Good
1,560 reviews

Food

6.8

Boarding

7.8

Comfort

7.4

Overall

7.5

Crew

8.1

Entertainment

6.8

Reviews

1 / 20
2.0
Mediocre

Juan,Dec 2025

EZE - PTY

The outbound flight from Boston was awful. The handicapped services were the worst i have ever seen. NEVER AGAIN. THIS WAS NOT WORTH ANYWHERE NEAR $4K.
United Airlines
7.4
Good
9,215 reviews
Copa Airlines
7.5
Good
1,560 reviews

Food

6.8

Boarding

7.8

Comfort

7.4

Overall

7.5

Crew

8.1

Entertainment

6.8

Reviews

1 / 20
2.0
Mediocre

Juan,Dec 2025

EZE - PTY

The outbound flight from Boston was awful. The handicapped services were the worst i have ever seen. NEVER AGAIN. THIS WAS NOT WORTH ANYWHERE NEAR $4K.
American Airlines
7.2
Good
11,206 reviews
Copa Airlines
7.5
Good
1,560 reviews

Food

6.8

Boarding

7.8

Comfort

7.4

Overall

7.5

Crew

8.1

Entertainment

6.8

Reviews

1 / 20
2.0
Mediocre

Juan,Dec 2025

EZE - PTY

The outbound flight from Boston was awful. The handicapped services were the worst i have ever seen. NEVER AGAIN. THIS WAS NOT WORTH ANYWHERE NEAR $4K.

Related info for your journey

Find useful and relevant information for your journey from Trinidad and Tobago to Illinois. 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 Illinois?

    Air Canada and Copa Airlines can get you from Trinidad and Tobago to Illinois in just under 11h 17m. Your travel time can differ by up to 1h 24m. There are 2697 mi between Trinidad and Tobago and Illinois. This flight may include one or multiple stops.

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

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

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

    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 Illinois.

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

    Yes. Cheapflights offers flight deals from Trinidad and Tobago to Illinois 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 Illinois?

    Currently, December is the cheapest month in which you can book a flight from Trinidad and Tobago to Illinois (average of $304). Flying from Trinidad and Tobago to Illinois in April is currently the most expensive (average of $632). 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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Trinidad and Tobago to Illinois

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Trinidad and Tobago to Illinois

Discover the top 3 airlines that operate flights from Trinidad and Tobago to Illinois. 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 January 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$290Average$706FlexibilityNo cancel feeOn-time69%
Copa AirlinesCheapest$299Average$542FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$562Average$698FlexibilityNo cancel feeOn-time71%

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