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Illinois

$350+ 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 4/6. Fares are subject to change and may not be available on all flights or dates of travel.
POS — ORD
Apr 19 — Apr 261
Sun 4/19
Sun 4/26
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 March 20, 2026.

This Copa Airlines deal was found by Cheapflights users on 3/17. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/172:17 pm
POS
-
ORD
1 stop11h 56m
Copa Airlines
Sun 4/263:05 pm
ORD
-
POS
1 stop9h 35m
Copa Airlines
Deal found 3/17$417
This Air Canada deal was found by Cheapflights users on 3/16. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/161:20 am
POS
-
ORD
1 stop12h 45m
Air Canada
Sun 4/268:40 am
ORD
-
POS
2 stops14h 40m
Air Canada
Deal found 3/16$423
This Mytrip deal was found by Cheapflights users on 3/18. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/221:20 am
POS
-
ORD
1 stop19h 25m
Air Canada
Mon 3/308:20 pm
ORD
-
POS
1 stop27h 00m
Air Canada
Deal found 3/18$469
This Mytrip deal was found by Cheapflights users on 3/18. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/51:20 am
POS
-
ORD
2 stops34h 33m
Air Canada
Tue 4/72:00 pm
ORD
-
POS
1 stop9h 20m
Air Canada
Deal found 3/18$495
This Kiwi.com deal was found by Cheapflights users on 3/17. 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.
Fri 5/110:10 am
POS
-
ORD
1 stop24h 26m
Multiple Airlines
Fri 5/811:51 am
ORD
-
POS
2 stops30h 04m
Multiple Airlines
Deal found 3/17$501
This Booking.com deal was found by Cheapflights users on 3/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/91:20 am
POS
-
STL
1 stop15h 05m
Air Canada
Sat 4/254:05 pm
STL
-
POS
1 stop31h 15m
Air Canada
Deal found 3/16$593
This United Airlines deal was found by Cheapflights users on 3/17. 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.
Wed 4/1512:30 am
POS
-
STL
1 stop16h 38m
United Airlines
Sun 4/266:00 am
STL
-
POS
1 stop16h 23m
United Airlines
Deal found 3/17$713
This American Airlines deal was found by Cheapflights users on 3/16. 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.
Wed 5/277:00 am
POS
-
STL
1 stop16h 58m
American Airlines
Wed 6/105:15 am
STL
-
POS
1 stop16h 46m
American Airlines
Deal found 3/16$715
This United Airlines deal was found by Cheapflights users on 3/17. 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.
Thu 8/2012:30 am
POS
-
STL
2 stops21h 52m
United Airlines
Sat 9/126:14 am
STL
-
POS
1 stop16h 09m
United Airlines
Deal found 3/17$736
This United Airlines deal was found by Cheapflights users on 3/16. 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 4/1512:30 am
POS
-
STL
1 stop16h 38m
United Airlines
Sat 4/257:45 am
STL
-
POS
2 stops14h 38m
United Airlines
Deal found 3/16$737
This United Airlines deal was found by Cheapflights users on 3/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/112:30 am
POS
-
STL
2 stops18h 46m
United Airlines
Sat 5/96:30 am
STL
-
POS
2 stops15h 53m
United Airlines
Deal found 3/18$759
This United Airlines deal was found by Cheapflights users on 3/17. 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.
Tue 4/712:30 am
POS
-
STL
2 stops21h 43m
United Airlines
Wed 4/2210:00 am
STL
-
POS
2 stops12h 23m
United Airlines
Deal found 3/17$764

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 March 20, 2026.

Round-trip from

$417
(Copa Airlines)

One-way from

$350
(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 March 20, 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

Fri 4/17

2:17 pm-1:13 am

1 stop11h 56m

Chicago O'Hare Intl

Sun 4/26

3:05 pm-1:40 am

1 stop9h 35m

$417

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 4/16

1:20 am-1:05 pm

1 stop12h 45m

Chicago O'Hare Intl

Sun 4/26

8:40 am-12:20 am

2 stops14h 40m

$423

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 5/1

10:10 am-11:54 pm

1 stop14h 44m

Chicago O'Hare Intl

Fri 5/8

8:10 am-6:55 pm

1 stop9h 45m

$487

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 4/30

9:10 am-11:59 pm

1 stop15h 49m

Chicago O'Hare Intl

Thu 5/7

3:05 pm-8:00 pm

1 stop27h 55m

$547

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

$566

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sat 5/16

2:45 pm-8:51 am

2 stops19h 06m

Chicago O'Hare Intl

Sat 5/30

1:55 pm-2:20 pm

2 stops23h 25m

$578
Quickest round-trip

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 8/2

2:19 pm-1:02 am

1 stop11h 43m

Chicago O'Hare Intl

Fri 8/7

3:21 pm-1:47 am

1 stop9h 26m

$586

Port of SpainSt. Louis

POS - STL

POSSTL

Port of Spain Piarco Intl

Thu 4/9

1:20 am-3:25 pm

1 stop15h 05m

Lambert-St Louis

Sat 4/25

4:05 pm-12:20 am

1 stop31h 15m

$593

Port of SpainSt. Louis

POS - STL

POSSTL

Port of Spain Piarco Intl

Wed 4/15

12:30 am-9:13 pm

2 stops21h 43m

Lambert-St Louis

Sun 4/26

6:00 am-11:23 pm

1 stop16h 23m

$713

Port of SpainSt. Louis

POS - STL

POSSTL

Port of Spain Piarco Intl

Wed 5/27

7:00 am-10:58 pm

1 stop16h 58m

Lambert-St Louis

Wed 6/10

11:12 am-11:01 pm

1 stop10h 49m

$715

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/19

Showing 1-10 of 16 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

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 $998). 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 March 20, 2026.
Read through reviews of airlines operating flights from Trinidad and Tobago to Illinois, such as Copa Airlines,United Airlines, andAmerican Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Copa Airlines
7.5
Good
1,573 reviews

Crew

8.1

Entertainment

6.8

Boarding

7.8

Food

6.8

Comfort

7.4

Overall

7.5

Reviews

1 / 20
2.0
Mediocre

Katerine,Mar 2026

LAX - PTY

Really i was expecting be more friendly with family’s, more when you travel with a infant. We expected like a priority to boarding or be friendly with the spots on the aeroplane.
Copa Airlines
7.5
Good
1,573 reviews
Copa Airlines
7.5
Good
1,573 reviews

Crew

8.1

Entertainment

6.8

Boarding

7.8

Food

6.8

Comfort

7.4

Overall

7.5

Reviews

1 / 20
2.0
Mediocre

Katerine,Mar 2026

LAX - PTY

Really i was expecting be more friendly with family’s, more when you travel with a infant. We expected like a priority to boarding or be friendly with the spots on the aeroplane.
United Airlines
7.4
Good
9,454 reviews
Copa Airlines
7.5
Good
1,573 reviews

Crew

8.1

Entertainment

6.8

Boarding

7.8

Food

6.8

Comfort

7.4

Overall

7.5

Reviews

1 / 20
2.0
Mediocre

Katerine,Mar 2026

LAX - PTY

Really i was expecting be more friendly with family’s, more when you travel with a infant. We expected like a priority to boarding or be friendly with the spots on the aeroplane.
American Airlines
7.1
Good
11,483 reviews
Copa Airlines
7.5
Good
1,573 reviews

Crew

8.1

Entertainment

6.8

Boarding

7.8

Food

6.8

Comfort

7.4

Overall

7.5

Reviews

1 / 20
2.0
Mediocre

Katerine,Mar 2026

LAX - PTY

Really i was expecting be more friendly with family’s, more when you travel with a infant. We expected like a priority to boarding or be friendly with the spots on the aeroplane.
Air Canada
7.1
Good
10,818 reviews
Copa Airlines
7.5
Good
1,573 reviews

Crew

8.1

Entertainment

6.8

Boarding

7.8

Food

6.8

Comfort

7.4

Overall

7.5

Reviews

1 / 20
2.0
Mediocre

Katerine,Mar 2026

LAX - PTY

Really i was expecting be more friendly with family’s, more when you travel with a infant. We expected like a priority to boarding or be friendly with the spots on the aeroplane.

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?

    Copa Airlines, Air Canada, and United Airlines can get you from Trinidad and Tobago to Illinois in just under 11h 56m. Your travel time can differ by up to 9h 47m. 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 $998). 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 4 airlines flying from Trinidad and Tobago to Illinois

Discover the top 4 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 March 20, 2026.
AirlineCheapestAverageFlexibilityOn-time
Copa AirlinesCheapest$299Average$374FlexibilityNo cancel feeOn-time70%
Air CanadaCheapest$322Average$506FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$559Average$792FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$562Average$790FlexibilityNo cancel feeOn-time71%

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