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$255+ Cheap flights from Trinidad 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 1/9. Fares are subject to change and may not be available on all flights or dates of travel.
POS — ORD
Dec 3 — Dec 101
Wed 12/3
Wed 12/10
1 adult, Economy
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Find flight deals from Trinidad to Illinois

Cheapest flights from Trinidad to Illinois
Explore the most affordable flight options available from Trinidad to Illinois. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 3, 2025.

This Air Canada deal was found by Cheapflights users on 11/2. 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 11/2$471
This American Airlines deal was found by Cheapflights users on 11/2. 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 stop12h 58mAmerican Airlines
Mon 12/17:17 pmORD - POS
1 stop18h 13mAmerican Airlines
Deal found 11/2$574
This American Airlines deal was found by Cheapflights users on 11/2. 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 11/237:19 amPOS - ORD
1 stop19h 18mAmerican Airlines
Sun 11/307:17 pmORD - POS
1 stop18h 13mAmerican Airlines
Deal found 11/2$580
This United Airlines deal was found by Cheapflights users on 11/2. 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.
Mon 12/11:30 amPOS - STL
2 stops23h 15mUnited Airlines
Tue 12/96:30 amSTL - POS
2 stops15h 53mUnited Airlines
Deal found 11/2$612
This American Airlines deal was found by Cheapflights users on 11/2. 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.
Tue 12/27:19 amPOS - STL
1 stop17h 08mAmerican Airlines
Tue 12/95:10 amSTL - POS
1 stop16h 49mAmerican Airlines
Deal found 11/2$613
This Kiwi.com deal was found by Cheapflights users on 11/1. 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.
Mon 12/299:10 amPOS - ORD
1 stop9h 50mMultiple Airlines
Sat 1/36:05 pmORD - POS
1 stop22h 50mMultiple Airlines
Deal found 11/1$655
This Mytrip deal was found by Cheapflights users on 11/3. 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.
Thu 12/189:10 amPOS - ORD
1 stop9h 50mMultiple Airlines
Thu 12/257:57 pmORD - POS
2 stops22h 03mMultiple Airlines
Deal found 11/3$669
This United Airlines deal was found by Cheapflights users on 11/1. 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 12/282:20 amPOS - ORD
1 stop11h 45mUnited Airlines
Sat 1/38:05 pmORD - POS
1 stop26h 18mUnited Airlines
Deal found 11/1$672

Cheap flight deals from Trinidad to Illinois

Keep the following information in mind while searching for Trinidad to Illinois flight deals. Data was last updated November 3, 2025.

Round-trip from

$463
(Priceline)

One-way from

$255
(Mytrip)
From Trinidad to Illinois
Search Deals
One-way flight from Trinidad to Illinois
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Trinidad 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 November 3, 2025.
Use the filters below to find and compare flights from Trinidad to Illinois that are best for you.

Fly from

Trinidad

Fly to

Illinois

Route

Depart

Return

Price

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 2/13

2:20 am-6:52 pm

2 stops18h 32m

Chicago O'Hare Intl

Tue 2/17

7:15 am-1:20 am

2 stops16h 05m

$463

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 11/25

2:15 am-3:10 pm

1 stop14h 55m

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

2:20 am-6:52 pm

2 stops42h 32m

Chicago O'Hare Intl

Tue 3/3

10:35 am-1:20 am

2 stops12h 45m

$483

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 11/26

7:19 am-6:17 pm

1 stop12h 58m

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

Mon 2/2

9:10 am-12:30 pm

1 stop29h 20m

Chicago O'Hare Intl

Fri 2/6

4:35 pm-8:20 pm

2 stops25h 45m

$577

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sat 2/14

4:47 pm-12:36 am

1 stop9h 49m

Chicago O'Hare Intl

Tue 2/17

9:08 pm-3:30 pm

2 stops16h 22m

$579

Port of SpainSt. Louis

POS - STL

POSSTL

Port of Spain Piarco Intl

Mon 12/1

1:30 am-10:04 am

1 stop10h 34m

Lambert-St Louis

Tue 12/9

10:00 am-12:23 am

2 stops36h 23m

$612

Port of SpainSt. Louis

POS - STL

POSSTL

Port of Spain Piarco Intl

Wed 1/14

4:30 pm-11:59 pm

1 stop9h 29m

Lambert-St Louis

Wed 5/27

5:25 am-9:25 pm

1 stop15h 00m

$613

Port of SpainSt. Louis

POS - STL

POSSTL

Port of Spain Piarco Intl

Tue 12/2

7:19 am-10:27 pm

1 stop17h 08m

Lambert-St Louis

Tue 12/9

5:10 am-11:59 pm

1 stop16h 49m

$613

Port of SpainSt. Louis

POS - STL

POSSTL

Port of Spain Piarco Intl

Thu 1/15

4:30 pm-11:41 am

2 stops21h 11m

Lambert-St Louis

Thu 5/28

5:25 am-9:25 pm

1 stop15h 00m

$617

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Showing 1-10 of 17 results
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Best time to book a flight from Trinidad to Illinois

Have a flexible travel schedule? Discover the best time to fly to Illinois from Trinidad 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 to Illinois

What is the cheapest month to book a flight from Trinidad to Illinois?

Currently, December is the cheapest month in which you can book a flight from Trinidad to Illinois (average of $304). Flying from Trinidad 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 LAZ to IL?

Find hourly flight availability from Trinidad 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 November 3, 2025.

When flying from Trinidad to Illinois, the time of day you fly usually plays a role in the price. Save by searching for a flight at noon, which can drop the price by up to 24% versus 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 November 3, 2025.
Get a feel of what it's like to fly with Copa Airlines, United Airlines, and American Airlines from Trinidad to Illinois by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Copa Airlines
7.6
Good
1,561 reviews

Comfort

7.4

Food

6.9

Entertainment

6.8

Crew

8.1

Overall

7.6

Boarding

7.8

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
1,561 reviews
Copa Airlines
7.6
Good
1,561 reviews

Comfort

7.4

Food

6.9

Entertainment

6.8

Crew

8.1

Overall

7.6

Boarding

7.8

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
8,997 reviews
Copa Airlines
7.6
Good
1,561 reviews

Comfort

7.4

Food

6.9

Entertainment

6.8

Crew

8.1

Overall

7.6

Boarding

7.8

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
11,036 reviews
Copa Airlines
7.6
Good
1,561 reviews

Comfort

7.4

Food

6.9

Entertainment

6.8

Crew

8.1

Overall

7.6

Boarding

7.8

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 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 to Illinois?

    For as low as $613, Air Canada can have you in Illinois from Trinidad in 9h 29m. The distance between Trinidad and Illinois is about 2641 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • Can I find deals for flights from Trinidad to Illinois that include hotel bookings?

    Yes. In addition to deals on Trinidad to Illinois flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Trinidad to Illinois?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Trinidad to Illinois.

  • Can I find deals for business class flights from Trinidad to Illinois?

    Yes. Cheapflights offers flight deals from Trinidad 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 to Illinois?

    Currently, December is the cheapest month in which you can book a flight from Trinidad to Illinois (average of $304). Flying from Trinidad 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

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Alternative routes for Trinidad 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 to Illinois

Discover the top 3 airlines that operate flights from Trinidad 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 November 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
Copa AirlinesCheapest$299Average$542FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$559Average$579FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$562Average$676FlexibilityNo cancel feeOn-time71%

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