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$444+ 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 2/12. Fares are subject to change and may not be available on all flights or dates of travel.
POS — ORD
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
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 December 18, 2025.

This Priceline deal was found by Cheapflights users on 12/16. 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.
Thu 12/252:15 amPOS - ORD
1 stop12h 46mAir Canada
Tue 12/302:00 pmORD - POS
1 stop9h 10mAir Canada
Deal found 12/16$669
This Gotogate deal was found by Cheapflights users on 12/16. 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.
Thu 12/252:15 amPOS - ORD
2 stops19h 55mMultiple Airlines
Tue 12/308:30 pmORD - POS
2 stops20h 55mMultiple Airlines
Deal found 12/16$758
This United Airlines deal was found by Cheapflights users on 12/16. 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 12/171:30 amPOS - ORD
1 stop15h 10mUnited Airlines
Tue 12/237:35 amORD - POS
1 stop14h 48mUnited Airlines
Deal found 12/16$1,001
This Kiwi.com deal was found by Cheapflights users on 12/17. 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
Tue 12/237:01 pmORD - POS
2 stops29h 12mMultiple Airlines
Deal found 12/17$1,025
This Expedia deal was found by Cheapflights users on 12/17. 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.
Sun 12/213:55 pmPOS - ORD
2 stops28h 51mJetBlue
Tue 12/237:41 pmORD - POS
2 stops16h 49mJetBlue
Deal found 12/17$1,057
This United Airlines deal was found by Cheapflights users on 12/17. 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 12/202:20 amPOS - ORD
1 stop11h 45mUnited Airlines
Tue 12/231:37 pmORD - POS
1 stop9h 28mUnited Airlines
Deal found 12/17$1,085
This American Airlines deal was found by Cheapflights users on 12/16. 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 12/186:02 amPOS - ORD
2 stops13h 47mAmerican Airlines
Tue 12/237:11 amORD - POS
2 stops14h 35mAmerican Airlines
Deal found 12/16$1,630

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 December 18, 2025.

Round-trip from

$444
(Expedia)
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 December 18, 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

Thu 2/12

8:50 am-11:10 pm

1 stop16h 20m

Chicago O'Hare Intl

Thu 2/19

10:00 am-7:17 am

2 stops19h 17m

$444

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 1/30

8:20 am-5:43 pm

2 stops35h 23m

Chicago O'Hare Intl

Fri 2/6

10:00 am-1:20 am

1 stop13h 20m

$478

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 2/12

12:22 pm-11:10 pm

1 stop12h 48m

Chicago O'Hare Intl

Thu 2/19

2:00 pm-1:20 am

1 stop9h 20m

$480

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 1/29

2:20 am-3:10 pm

1 stop14h 50m

Chicago O'Hare Intl

Fri 2/6

10:00 am-1:20 am

1 stop13h 20m

$513

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 2/1

8:20 am-6:32 pm

1 stop12h 12m

Chicago O'Hare Intl

Sun 2/8

10:00 am-1:20 am

1 stop13h 20m

$529

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

8:02 am-1:46 am

1 stop16h 44m

$584

Port of SpainSt. Louis

POS - STL

POSSTL

Port of Spain Piarco Intl

Thu 1/22

1:30 am-3:52 pm

1 stop16h 22m

Lambert-St Louis

Sun 1/25

10:07 am-12:23 am

1 stop12h 16m

$613

Port of SpainSt. Louis

POS - STL

POSSTL

Port of Spain Piarco Intl

Thu 1/15

4:30 pm-11:59 pm

1 stop9h 29m

Lambert-St Louis

Thu 5/28

10:53 am-9:25 pm

1 stop9h 32m

$613

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 5/6

3:10 pm-8:49 am

2 stops18h 39m

Chicago O'Hare Intl

Sun 5/10

7:17 pm-2:00 pm

1 stop17h 43m

$640

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

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 December 18, 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 December 18, 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
1,556 reviews

Entertainment

6.8

Food

6.8

Boarding

7.8

Comfort

7.4

Crew

8.1

Overall

7.6

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
1,556 reviews
Copa Airlines
7.6
Good
1,556 reviews

Entertainment

6.8

Food

6.8

Boarding

7.8

Comfort

7.4

Crew

8.1

Overall

7.6

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
9,091 reviews
Copa Airlines
7.6
Good
1,556 reviews

Entertainment

6.8

Food

6.8

Boarding

7.8

Comfort

7.4

Crew

8.1

Overall

7.6

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
11,054 reviews
Copa Airlines
7.6
Good
1,556 reviews

Entertainment

6.8

Food

6.8

Boarding

7.8

Comfort

7.4

Crew

8.1

Overall

7.6

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?

    JetBlue, Air Canada, and United Airlines can get you from Trinidad and Tobago to Illinois in just under 14h 50m. Your travel time can differ by up to 1h 32m. 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Copa AirlinesCheapest$299Average$542FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$474Average$579FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$562Average$698FlexibilityNo cancel feeOn-time71%

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