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$439+ Cheap flights from Trinidad and Tobago to Illinois

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 1/5. Fares are subject to change and may not be available on all flights or dates of travel.
POS — ORD
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Find 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 October 30, 2025.

This Air Canada deal was found by Cheapflights users on 10/30. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/252:15 amPOS - ORD
2 stops14h 40mAir Canada
Mon 12/18:15 pmORD - POS
1 stop26h 55mAir Canada
Deal found 10/30$471
This United Airlines deal was found by Cheapflights users on 10/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/201:30 amPOS - ORD
1 stop23h 07mUnited Airlines
Thu 1/12:37 pmORD - POS
1 stop8h 28mUnited Airlines
Deal found 10/29$571
This American Airlines deal was found by Cheapflights users on 10/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/267:19 amPOS - ORD
1 stop17h 40mAmerican Airlines
Sun 11/3012:19 amORD - POS
1 stop13h 11mAmerican Airlines
Deal found 10/30$574
This American Airlines deal was found by Cheapflights users on 10/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/234:30 pmPOS - ORD
1 stop18h 35mAmerican Airlines
Sun 11/307:17 pmORD - POS
1 stop18h 13mAmerican Airlines
Deal found 10/30$580
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Sun 12/217:35 pmPOS - ORD
1 stop23h 25mMultiple Airlines
Wed 12/317:30 amORD - POS
2 stops16h 18mMultiple Airlines
Deal found 10/29$581
This United Airlines deal was found by Cheapflights users on 10/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/221:30 amPOS - ORD
1 stop32h 11mUnited Airlines
Sun 11/3011:55 pmORD - POS
1 stop22h 28mUnited Airlines
Deal found 10/30$593
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Sun 12/217:35 pmPOS - ORD
1 stop23h 25mMultiple Airlines
Sat 1/35:45 amORD - POS
2 stops12h 35mMultiple Airlines
Deal found 10/29$598
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Sun 12/219:10 amPOS - ORD
1 stop9h 50mMultiple Airlines
Thu 1/17:20 amORD - POS
2 stops27h 51mMultiple Airlines
Deal found 10/29$617
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Sun 12/219:10 amPOS - ORD
1 stop9h 50mMultiple Airlines
Tue 12/307:30 amORD - POS
2 stops28h 01mMultiple Airlines
Deal found 10/29$639

Cheap 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 October 30, 2025.

Round-trip from

$471
(Air Canada)

One-way from

$439
(Kiwi.com)
From Trinidad and Tobago to Illinois
Search Deals
One-way flight 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 October 30, 2025.
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

Tue 11/25

2:15 am-1:01 pm

1 stop12h 46m

Chicago O'Hare Intl

Mon 12/1

8:15 pm-1:10 am

1 stop26h 55m

$471

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 2/26

2:15 am-6:52 pm

2 stops42h 37m

Chicago O'Hare Intl

Tue 3/3

10:00 am-1:10 am

1 stop13h 10m

$483

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sat 12/20

1:30 am-10:37 pm

1 stop23h 07m

Chicago O'Hare Intl

Wed 12/31

8:54 am-12:23 am

1 stop13h 29m

$571

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sat 12/20

1:30 am-10:37 pm

1 stop23h 07m

Chicago O'Hare Intl

Thu 1/1

2:37 pm-1:05 am

1 stop8h 28m

$571

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 11/26

7:19 am-10:59 pm

1 stop17h 40m

Chicago O'Hare Intl

Mon 12/1

7:17 pm-3:30 pm

1 stop18h 13m

$574

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 2/26

1:30 am-12:37 pm

1 stop13h 07m

Chicago O'Hare Intl

Tue 3/3

2:30 pm-1:05 am

1 stop8h 35m

$574

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 11/23

4:30 pm-9:05 am

1 stop18h 35m

Chicago O'Hare Intl

Sun 11/30

7:17 pm-3:30 pm

1 stop18h 13m

$580

Port of SpainSt. Louis

POS - STL

POSSTL

Port of Spain Piarco Intl

Sat 2/28

1:30 am-9:23 am

1 stop9h 53m

Lambert-St Louis

Tue 3/3

6:00 am-12:23 am

1 stop16h 23m

$637

Port of SpainSt. Louis

POS - STL

POSSTL

Port of Spain Piarco Intl

Sun 3/1

4:47 pm-12:27 pm

2 stops21h 40m

Lambert-St Louis

Tue 3/3

3:34 pm-3:30 pm

2 stops21h 56m

$771

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Mon 1/5

3:40 am-5:00 pm

2 stops39h 20m

$439

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 12 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.

What is the cheapest time of day to fly from TT to IL?

Find hourly flight availability from Trinidad and Tobago to Illinois. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 30, 2025.

It’s optimal to fly from Trinidad and Tobago to Illinois at noon. By choosing this option you can save up to 24% on the cost of your flight, compared to a flight in the afternoon.

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 October 30, 2025.
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
7.6
Good
1,563 reviews

Comfort

7.4

Food

6.8

Entertainment

6.8

Boarding

7.8

Overall

7.6

Crew

8.1

Reviews

1 / 20
4.0
Okay

Juan Pablo,Sep 2025

PTY - VVI

not a good expirience, the plane was packed, the seats wear very unconftrable, coudent conect with the entratainmente service on the plane, the onboarding was in charge of a very angry lady i really had a unplesent trip
Copa Airlines
7.6
Good
1,563 reviews
Copa Airlines
7.6
Good
1,563 reviews

Comfort

7.4

Food

6.8

Entertainment

6.8

Boarding

7.8

Overall

7.6

Crew

8.1

Reviews

1 / 20
4.0
Okay

Juan Pablo,Sep 2025

PTY - VVI

not a good expirience, the plane was packed, the seats wear very unconftrable, coudent conect with the entratainmente service on the plane, the onboarding was in charge of a very angry lady i really had a unplesent trip
United Airlines
7.4
Good
8,998 reviews
Copa Airlines
7.6
Good
1,563 reviews

Comfort

7.4

Food

6.8

Entertainment

6.8

Boarding

7.8

Overall

7.6

Crew

8.1

Reviews

1 / 20
4.0
Okay

Juan Pablo,Sep 2025

PTY - VVI

not a good expirience, the plane was packed, the seats wear very unconftrable, coudent conect with the entratainmente service on the plane, the onboarding was in charge of a very angry lady i really had a unplesent trip
American Airlines
7.2
Good
11,030 reviews
Copa Airlines
7.6
Good
1,563 reviews

Comfort

7.4

Food

6.8

Entertainment

6.8

Boarding

7.8

Overall

7.6

Crew

8.1

Reviews

1 / 20
4.0
Okay

Juan Pablo,Sep 2025

PTY - VVI

not a good expirience, the plane was packed, the seats wear very unconftrable, coudent conect with the entratainmente service on the plane, the onboarding was in charge of a very angry lady i really had a unplesent trip

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 United Airlines can get you from Trinidad and Tobago to Illinois in just under 12h 46m. Your travel time can differ by up to 10h 21m. 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

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

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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Copa AirlinesCheapest$299Average$542FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$559Average$579FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$561Average$662FlexibilityNo cancel feeOn-time71%

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