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$447+ Cheap flights from Trinidad and Tobago to Chicago (CHI)

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 9/9. Fares are subject to change and may not be available on all flights or dates of travel.
POS — CHI
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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Cheap flight deals from Trinidad and Tobago to Chicago

Keep the following information in mind while searching for Trinidad and Tobago to Chicago flight deals. Data was last updated July 31, 2025.

Round-trip from

$447
(Kiwi.com)
From Trinidad and Tobago to Chicago (CHI)
Search Deals

Find flight deals from Trinidad and Tobago to Chicago

Cheapest flights from Trinidad and Tobago to Chicago
Explore the most affordable flight options available from Trinidad and Tobago to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 31, 2025.

This Kiwi.com deal was found by Cheapflights users on 7/29. 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.
Tue 9/99:10 amPOS - ORD
1 stop25h 08mMultiple Airlines
Tue 9/1610:27 amORD - POS
1 stop31h 28mMultiple Airlines
Deal found 7/29$447
This Copa Airlines deal was found by Cheapflights users on 7/30. 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 10/172:40 pmPOS - ORD
1 stop10h 41mCopa Airlines
Fri 10/243:07 pmORD - POS
1 stop9h 39mCopa Airlines
Deal found 7/30$562
This Priceline deal was found by Cheapflights users on 7/29. 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 11/22:15 amPOS - ORD
1 stop12h 46mAir Canada
Mon 11/108:20 pmORD - POS
1 stop26h 55mAir Canada
Deal found 7/29$565
This United Airlines deal was found by Cheapflights users on 7/31. 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 9/812:30 amPOS - ORD
1 stop20h 28mUnited Airlines
Tue 9/166:00 amORD - POS
1 stop16h 23mUnited Airlines
Deal found 7/31$573
This American Airlines deal was found by Cheapflights users on 7/31. 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 9/93:25 pmPOS - ORD
2 stops20h 18mAmerican Airlines
Tue 9/168:34 pmORD - POS
2 stops16h 42mAmerican Airlines
Deal found 7/31$578
This Expedia deal was found by Cheapflights users on 7/30. 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.
Wed 12/243:56 pmPOS - ORD
2 stops19h 28mJetBlue
Fri 1/26:14 pmORD - POS
2 stops35h 00mJetBlue
Deal found 7/30$744

Cheapflights Fare Finder

 
Customize your flight search to find flights from Trinidad and Tobago to Chicago 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 July 31, 2025.
Use the filters below to find and compare flights from Trinidad and Tobago to Chicago that are best for you.

Fly from

Trinidad and Tobago

Fly to

Chicago

Route

Depart

Return

Price

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 9/9

9:10 am-9:18 am

1 stop25h 08m

Chicago O'Hare Intl

Tue 9/16

10:27 am-6:55 pm

1 stop31h 28m

$447

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 10/17

2:40 pm-12:21 am

1 stop10h 41m

Chicago O'Hare Intl

Fri 10/24

3:07 pm-1:46 am

1 stop9h 39m

$562

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 11/2

2:15 am-1:01 pm

1 stop12h 46m

Chicago O'Hare Intl

Mon 11/10

8:20 pm-1:15 am

1 stop26h 55m

$565

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Mon 9/8

12:30 am-7:58 pm

1 stop20h 28m

Chicago O'Hare Intl

Tue 9/16

6:00 am-11:23 pm

1 stop16h 23m

$573

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 9/9

3:25 pm-10:43 am

2 stops20h 18m

Chicago O'Hare Intl

Tue 9/16

8:34 pm-2:16 pm

2 stops16h 42m

$578

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 12/24

3:56 pm-9:24 am

2 stops19h 28m

Chicago O'Hare Intl

Fri 1/2

6:14 pm-7:14 am

2 stops35h 00m

$744

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Best time to book a flight from Trinidad and Tobago to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago 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

What is the cheapest month to book a flight from Trinidad and Tobago to Chicago?

Currently, August is the cheapest month in which you can book a flight from Trinidad and Tobago to Chicago (average of $245). Flying from Trinidad and Tobago to Chicago in March is currently the most expensive (average of $321). 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 CHI?

Find hourly flight availability from Trinidad and Tobago to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 31, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Trinidad and Tobago to Chicago as you normally would.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated July 31, 2025.
Read reviews from past customers who have flown Copa Airlines, United Airlines, and JetBlue from Trinidad and Tobago to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Copa Airlines
7.5
Good
1,493 reviews

Comfort

7.4

Overall

7.5

Boarding

7.8

Crew

8.1

Entertainment

6.8

Food

6.8

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.
Copa Airlines
7.5
Good
1,493 reviews
Copa Airlines
7.5
Good
1,493 reviews

Comfort

7.4

Overall

7.5

Boarding

7.8

Crew

8.1

Entertainment

6.8

Food

6.8

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.
United Airlines
7.4
Good
8,900 reviews
Copa Airlines
7.5
Good
1,493 reviews

Comfort

7.4

Overall

7.5

Boarding

7.8

Crew

8.1

Entertainment

6.8

Food

6.8

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.
JetBlue
7.3
Good
2,914 reviews
Copa Airlines
7.5
Good
1,493 reviews

Comfort

7.4

Overall

7.5

Boarding

7.8

Crew

8.1

Entertainment

6.8

Food

6.8

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.
American Airlines
7.2
Good
10,000 reviews
Copa Airlines
7.5
Good
1,493 reviews

Comfort

7.4

Overall

7.5

Boarding

7.8

Crew

8.1

Entertainment

6.8

Food

6.8

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.
Air Canada
7.1
Good
9,851 reviews
Copa Airlines
7.5
Good
1,493 reviews

Comfort

7.4

Overall

7.5

Boarding

7.8

Crew

8.1

Entertainment

6.8

Food

6.8

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.

Related info for your journey

Find useful and relevant information for your journey from Trinidad and Tobago to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • Can I find deals for flights from Trinidad and Tobago to Chicago that include hotel bookings?

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

  • How can I find direct flights from Trinidad and Tobago to Chicago?

    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 Chicago.

  • Can I find deals for business class flights from Trinidad and Tobago to Chicago?

    Yes. Cheapflights offers flight deals from Trinidad and Tobago to Chicago 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?

    Currently, August is the cheapest month in which you can book a flight from Trinidad and Tobago to Chicago (average of $245). Flying from Trinidad and Tobago to Chicago in March is currently the most expensive (average of $321). 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?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton

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Top 2 airlines flying from Trinidad and Tobago to Chicago

Discover the top 2 airlines that operate flights from Trinidad and Tobago to Chicago. 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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$493Average$579FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$561Average$662FlexibilityNo cancel feeOn-time71%

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