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O'Hare Intl

$255+ Cheap flights from Trinidad and Tobago to O'Hare Intl (ORD)

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 2 — Dec 91
Tue 12/2
Tue 12/9
1 adult, Economy
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Find flight deals from Trinidad and Tobago to O'Hare Intl

Cheapest flights from Trinidad and Tobago to O'Hare Intl
Explore the most affordable flight options available from Trinidad and Tobago to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 2, 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 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 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
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
Fri 1/26:40 amORD - POS
2 stops29h 15mMultiple Airlines
Deal found 11/1$701

Cheap flight deals from Trinidad and Tobago to O'Hare Intl

Keep the following information in mind while searching for Trinidad and Tobago to O'Hare Intl flight deals. Data was last updated November 2, 2025.

Round-trip from

$471
(Air Canada)

One-way from

$255
(Mytrip)
From Trinidad and Tobago to Chicago O'Hare Intl
Search Deals
One-way flight from Trinidad and Tobago to Chicago O'Hare Intl
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Trinidad and Tobago to O'Hare Intl 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 2, 2025.
Use the filters below to find and compare flights from Trinidad and Tobago to Chicago O'Hare Intl Airport that are best for you.

Fly from

Trinidad and Tobago

Fly to

O'Hare Intl

Route

Depart

Return

Price

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

10:00 am-1:20 am

1 stop13h 20m

$483

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 2/1

12:10 am-12:57 pm

1 stop14h 47m

Chicago O'Hare Intl

Fri 2/6

6:05 am-7:30 pm

1 stop11h 25m

$561

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

Thu 2/5

10:10 am-7:29 pm

1 stop11h 19m

Chicago O'Hare Intl

Mon 2/9

4:35 pm-6:25 pm

1 stop23h 50m

$644

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 1/9

10:10 am-9:00 pm

1 stop12h 50m

$255

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 1/8

2:20 am-2:55 pm

2 stops38h 35m

$434

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 1/8

1:30 am-6:37 pm

3 stops19h 07m

$2,228

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/2

Best time to book a flight from Trinidad and Tobago to O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl 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 Chicago O'Hare Intl Airport

What is the cheapest month to book a flight from Trinidad and Tobago to Chicago O'Hare Intl Airport?

Currently, December is the cheapest month in which you can book a flight from Trinidad and Tobago to Chicago O'Hare Intl Airport (average of $304). Flying from Trinidad and Tobago to Chicago O'Hare Intl Airport 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 ORD?

Find hourly flight availability from Trinidad and Tobago to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 2, 2025.

It’s typically best to fly out from Trinidad and Tobago to Chicago O'Hare Intl Airport at noon. Doing so could potentially save you 19% on the flight price compared to flying in the afternoon, which is usually more expensive.

Reviews of airlines servicing O'Hare Intl

Get insights into the airlines that provide service to O'Hare Intl. 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 O'Hare Intl. Reviews last updated November 2, 2025.
Get a feel of what it's like to fly with Copa Airlines, United Airlines, and American Airlines from Trinidad and Tobago to Chicago O'Hare Intl Airport 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

Entertainment

6.8

Crew

8.1

Overall

7.6

Boarding

7.8

Food

6.9

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

Entertainment

6.8

Crew

8.1

Overall

7.6

Boarding

7.8

Food

6.9

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
8,993 reviews
Copa Airlines
7.6
Good
1,561 reviews

Comfort

7.4

Entertainment

6.8

Crew

8.1

Overall

7.6

Boarding

7.8

Food

6.9

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
11,032 reviews
Copa Airlines
7.6
Good
1,561 reviews

Comfort

7.4

Entertainment

6.8

Crew

8.1

Overall

7.6

Boarding

7.8

Food

6.9

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 O'Hare Intl. 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 Chicago O'Hare Intl Airport?

    Air Canada can get you from Trinidad and Tobago to Chicago O'Hare Intl Airport in just under 14h 55m. Your travel time can differ by up to . There are 2697 mi between Trinidad and Tobago and Chicago O'Hare Intl Airport.

  • Can I find deals for flights from Trinidad and Tobago to O'Hare Intl that include hotel bookings?

    Yes. In addition to deals on Trinidad and Tobago to O'Hare Intl flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Trinidad and Tobago to O'Hare Intl?

    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 O'Hare Intl.

  • Can I find deals for business class flights from Trinidad and Tobago to O'Hare Intl?

    Yes. Cheapflights offers flight deals from Trinidad and Tobago to O'Hare Intl 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 Chicago O'Hare Intl Airport?

    Currently, December is the cheapest month in which you can book a flight from Trinidad and Tobago to Chicago O'Hare Intl Airport (average of $304). Flying from Trinidad and Tobago to Chicago O'Hare Intl Airport 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

Traveling to a place near Chicago O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Schaumburg
Rosemont
Skokie
Des Plaines
Gurnee
Hoffman Estates
Beloit
Elgin
Oak Brook
Elk Grove Village
Naperville
Racine
Downers Grove
Rockford
Orland Park
Merrillville
Bridgeview
Warrenville
Waukegan
Aurora

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Alternative routes for Trinidad and Tobago to O'Hare Intl

See prices for flight routes from nearby airports that may be better suited for you.
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Port Au Prince to Midway flights

Top 3 airlines flying from Trinidad and Tobago to O'Hare Intl

Discover the top 3 airlines that operate flights from Trinidad and Tobago to O'Hare Intl. 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 2, 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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