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$314+ 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 12/24. Fares are subject to change and may not be available on all flights or dates of travel.
POS — ORD
Oct 15 — Oct 221
Wed 10/15
Wed 10/22
1 adult, Economy
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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 September 15, 2025.

Round-trip from

$452
(Priceline)

One-way from

$314
(United Airlines)
From Trinidad and Tobago to Illinois
Search Deals
One-way flight from Trinidad and Tobago to Illinois
Search Deals

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 September 15, 2025.

This Priceline deal was found by Cheapflights users on 9/14. 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.
Tue 10/281:15 amPOS - ORD
2 stops43h 45mAir Canada
Wed 11/58:15 pmORD - POS
1 stop26h 55mAir Canada
Deal found 9/14$452
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 10/292:27 pmPOS - ORD
2 stops19h 55mMultiple Airlines
Wed 11/55:59 pmORD - POS
1 stop24h 01mMultiple Airlines
Deal found 9/14$463
This Copa Airlines deal was found by Cheapflights users on 9/14. 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 10/283:51 amPOS - ORD
1 stop10h 50mCopa Airlines
Wed 11/56:56 amORD - POS
1 stop16h 52mCopa Airlines
Deal found 9/14$562
This United Airlines deal was found by Cheapflights users on 9/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/1512:30 amPOS - STL
2 stops35h 19mUnited Airlines
Thu 10/235:00 amSTL - POS
2 stops17h 23mUnited Airlines
Deal found 9/15$612
This American Airlines deal was found by Cheapflights users on 9/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/163:25 pmPOS - STL
2 stops17h 51mAmerican Airlines
Thu 10/236:08 pmSTL - POS
2 stops19h 17mAmerican Airlines
Deal found 9/15$617
This American Airlines deal was found by Cheapflights users on 9/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/257:00 amPOS - STL
2 stops17h 18mAmerican Airlines
Fri 10/316:03 amSTL - POS
2 stops14h 17mAmerican Airlines
Deal found 9/15$639
This United Airlines deal was found by Cheapflights users on 9/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/112:30 amPOS - STL
1 stop10h 22mUnited Airlines
Thu 10/236:30 amSTL - POS
2 stops15h 53mUnited Airlines
Deal found 9/15$640
This United Airlines deal was found by Cheapflights users on 9/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2412:30 amPOS - STL
2 stops14h 57mUnited Airlines
Tue 10/145:28 pmSTL - POS
2 stops28h 55mUnited Airlines
Deal found 9/15$641
This American Airlines deal was found by Cheapflights users on 9/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/253:25 pmPOS - STL
1 stop9h 34mAmerican Airlines
Tue 10/146:08 pmSTL - POS
2 stops19h 17mAmerican Airlines
Deal found 9/15$645
This American Airlines deal was found by Cheapflights users on 9/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/23:25 pmPOS - STL
1 stop9h 34mAmerican Airlines
Thu 10/236:08 pmSTL - POS
1 stop26h 12mAmerican Airlines
Deal found 9/15$652
This United Airlines deal was found by Cheapflights users on 9/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/2412:30 amPOS - STL
2 stops22h 07mUnited Airlines
Fri 10/3111:20 amSTL - POS
1 stop11h 03mUnited Airlines
Deal found 9/15$658
This American Airlines deal was found by Cheapflights users on 9/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/23:25 pmPOS - STL
1 stop9h 34mAmerican Airlines
Sat 10/115:23 amSTL - POS
1 stop8h 02mAmerican Airlines
Deal found 9/15$669

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 September 15, 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 10/28

1:15 am-8:00 pm

2 stops43h 45m

Chicago O'Hare Intl

Wed 11/5

8:15 pm-1:10 am

1 stop26h 55m

$452

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 10/29

2:27 pm-9:22 am

2 stops19h 55m

Chicago O'Hare Intl

Wed 11/5

5:59 pm-8:00 pm

1 stop24h 01m

$463

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 10/28

3:51 am-1:41 pm

1 stop10h 50m

Chicago O'Hare Intl

Wed 11/5

6:56 am-1:48 am

1 stop16h 52m

$562

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 2/26

1:30 am-11:09 am

1 stop11h 39m

Chicago O'Hare Intl

Tue 3/3

7:35 am-12:23 am

1 stop14h 48m

$574

Port of SpainSt. Louis

POS - STL

POSSTL

Port of Spain Piarco Intl

Wed 10/15

12:30 am-9:52 am

1 stop10h 22m

Lambert-St Louis

Thu 10/23

11:06 am-11:23 pm

1 stop11h 17m

$612

Port of SpainSt. Louis

POS - STL

POSSTL

Port of Spain Piarco Intl

Thu 10/16

10:10 am-10:37 am

2 stops25h 27m

Lambert-St Louis

Thu 10/23

10:57 am-8:00 pm

1 stop8h 03m

$612

Port of SpainSt. Louis

POS - STL

POSSTL

Port of Spain Piarco Intl

Sat 10/25

7:00 am-11:56 pm

1 stop17h 56m

Lambert-St Louis

Fri 10/31

6:03 am-9:20 pm

2 stops14h 17m

$639

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 2/26

2:15 am-5:48 pm

1 stop17h 33m

Chicago O'Hare Intl

Tue 3/3

7:15 am-1:10 am

2 stops15h 55m

$640

Port of SpainSt. Louis

POS - STL

POSSTL

Port of Spain Piarco Intl

Wed 10/1

12:30 am-9:52 am

1 stop10h 22m

Lambert-St Louis

Thu 10/23

11:06 am-11:23 pm

1 stop11h 17m

$640

Port of SpainSt. Louis

POS - STL

POSSTL

Port of Spain Piarco Intl

Wed 9/24

12:30 am-10:49 am

2 stops35h 19m

Lambert-St Louis

Tue 10/14

11:06 am-11:23 pm

1 stop11h 17m

$641

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 21 results
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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, August is the cheapest month in which you can book a flight from Trinidad and Tobago to Illinois (average of $245). Flying from Trinidad and Tobago to Illinois in March is currently the most expensive (average of $321). 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 September 15, 2025.

When flying from Trinidad and Tobago to Illinois, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 September 15, 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
1,531 reviews

Comfort

7.4

Food

6.8

Overall

7.6

Boarding

7.8

Crew

8.1

Entertainment

6.8

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
1,531 reviews
Copa Airlines
7.6
Good
1,531 reviews

Comfort

7.4

Food

6.8

Overall

7.6

Boarding

7.8

Crew

8.1

Entertainment

6.8

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
8,929 reviews
Copa Airlines
7.6
Good
1,531 reviews

Comfort

7.4

Food

6.8

Overall

7.6

Boarding

7.8

Crew

8.1

Entertainment

6.8

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
10,000 reviews
Copa Airlines
7.6
Good
1,531 reviews

Comfort

7.4

Food

6.8

Overall

7.6

Boarding

7.8

Crew

8.1

Entertainment

6.8

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, Copa Airlines, and United Airlines can get you from Trinidad and Tobago to Illinois in just under 10h 22m. Your travel time can differ by up to 33h 23m. There are 2641 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, August is the cheapest month in which you can book a flight from Trinidad and Tobago to Illinois (average of $245). Flying from Trinidad and Tobago to Illinois in March is currently the most expensive (average of $321). 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 September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Copa AirlinesCheapest$304Average$543FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$559Average$581FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$561Average$662FlexibilityNo cancel feeOn-time71%

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