Illinois

$601+ 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 6/21. Fares are subject to change and may not be available on all flights or dates of travel.
POS — ORD
Jul 19 — Jul 261
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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 June 19, 2026.

This Priceline deal was found by Cheapflights users on 6/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/211:25 am
POS
-
ORD
2 stops18h 27m
Air Canada
Mon 6/292:15 pm
ORD
-
POS
1 stop9h 15m
Air Canada
Deal found 6/17$601
This Mytrip deal was found by Cheapflights users on 6/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/311:25 am
POS
-
ORD
1 stop16h 32m
Air Canada
Mon 9/79:50 am
ORD
-
POS
1 stop13h 25m
Air Canada
Deal found 6/17$605
This Air Canada deal was found by Cheapflights users on 6/15. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/101:25 am
POS
-
ORD
1 stop14h 30m
Air Canada
Sat 8/296:21 pm
ORD
-
POS
2 stops28h 54m
Air Canada
Deal found 6/15$630
This Priceline deal was found by Cheapflights users on 6/18. 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 7/11:25 am
POS
-
ORD
2 stops18h 22m
Air Canada
Sun 7/59:50 am
ORD
-
POS
1 stop13h 25m
Air Canada
Deal found 6/18$632
This Air Canada deal was found by Cheapflights users on 6/15. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/81:25 am
POS
-
ORD
2 stops34h 55m
Air Canada
Sat 8/298:40 pm
ORD
-
POS
1 stop26h 35m
Air Canada
Deal found 6/15$633
This Air Canada deal was found by Cheapflights users on 6/15. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/81:25 am
POS
-
ORD
2 stops34h 55m
Air Canada
Fri 8/288:45 am
ORD
-
POS
2 stops14h 30m
Air Canada
Deal found 6/15$636
This Gotogate deal was found by Cheapflights users on 6/16. 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.
Fri 6/191:25 am
POS
-
STL
1 stop11h 56m
Air Canada
Sat 7/1812:10 pm
STL
-
POS
2 stops35h 05m
Air Canada
Deal found 6/16$647
This Air Canada deal was found by Cheapflights users on 6/18. 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 7/81:25 am
POS
-
ORD
1 stop12h 57m
Air Canada
Wed 7/222:15 pm
ORD
-
POS
1 stop9h 00m
Air Canada
Deal found 6/18$649
This Gotogate deal was found by Cheapflights users on 6/16. 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.
Wed 7/151:25 am
POS
-
ORD
1 stop12h 57m
Air Canada
Tue 7/213:50 pm
ORD
-
POS
1 stop31h 25m
Air Canada
Deal found 6/16$659
This United Airlines deal was found by Cheapflights users on 6/15. 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.
Sun 11/221:30 am
POS
-
STL
1 stop10h 12m
United Airlines
Tue 12/86:15 am
STL
-
POS
1 stop16h 08m
United Airlines
Deal found 6/15$692
This United Airlines deal was found by Cheapflights users on 6/15. 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 11/201:30 am
POS
-
STL
1 stop10h 12m
United Airlines
Tue 12/811:00 am
STL
-
POS
1 stop11h 23m
United Airlines
Deal found 6/15$715
This Gotogate deal was found by Cheapflights users on 6/16. 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.
Sat 6/209:00 am
POS
-
STL
2 stops28h 21m
Multiple Airlines
Sat 7/1812:10 pm
STL
-
POS
2 stops35h 05m
Multiple Airlines
Deal found 6/16$759

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 June 19, 2026.

Round-trip from

$605
(Mytrip)
From Trinidad and Tobago to Illinois

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 June 19, 2026.
Use the filters below to find and compare flights from Trinidad and Tobago to Illinois 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

Wed 7/1

1:25 am-6:47 pm

2 stops18h 22m

Chicago O'Hare Intl

Sun 7/5

9:50 am-12:15 am

1 stop13h 25m

$632

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 7/8

1:25 am-1:22 pm

1 stop12h 57m

Chicago O'Hare Intl

Wed 7/22

8:45 am-12:15 am

2 stops14h 30m

$652

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 7/3

1:25 am-6:47 pm

2 stops18h 22m

Chicago O'Hare Intl

Thu 7/9

2:08 pm-12:15 am

2 stops33h 07m

$663

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 7/22

3:50 am-4:00 am

1 stop25h 10m

Chicago O'Hare Intl

Sun 7/26

3:21 pm-1:16 pm

1 stop20h 55m

$680

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 9/6

2:00 am-2:47 pm

1 stop13h 47m

Chicago O'Hare Intl

Tue 9/15

8:50 am-11:23 pm

1 stop13h 33m

$690
Quickest round-trip

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sat 7/11

12:30 am-11:01 am

1 stop11h 31m

Chicago O'Hare Intl

Tue 9/1

2:31 pm-12:50 am

1 stop9h 19m

$691

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 7/14

12:30 am-12:45 am

1 stop25h 15m

Chicago O'Hare Intl

Mon 8/31

8:40 am-12:50 am

1 stop15h 10m

$692

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 7/14

12:30 am-12:45 am

1 stop25h 15m

Chicago O'Hare Intl

Thu 9/3

1:30 pm-12:50 am

1 stop10h 20m

$692

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 7/22

2:00 am-11:04 am

1 stop10h 04m

Chicago O'Hare Intl

Mon 7/27

8:51 am-11:23 pm

1 stop13h 32m

$692

Port of SpainSt. Louis

POS - STL

POSSTL

Port of Spain Piarco Intl

Sun 11/22

1:30 am-2:18 pm

2 stops14h 48m

Lambert-St Louis

Tue 12/8

6:40 am-12:23 am

2 stops15h 43m

$694

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/18

Showing 1-10 of 14 resultsSorted by cheapest first
1
2

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
No data available for this route at this time. Please check back soon.

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 June 19, 2026.
Read through reviews of airlines operating flights from Trinidad and Tobago to Illinois, such as United Airlines and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Crew

8.1

Food

6.7

Overall

7.4

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.

Crew

8.1

Food

6.7

Overall

7.4

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.

Crew

8.1

Food

6.7

Overall

7.4

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.

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 14h 48m. Your travel time can differ by up to 10h 22m. 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.

See more FAQs

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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.

Top 2 airlines flying from Trinidad and Tobago to Illinois

Discover the top 2 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 June 19, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$572Average$720FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$573Average$799FlexibilityNo cancel feeOn-time71%

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