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$314+ Cheap flights from Trinidad and Tobago to Chicago (CHI)

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 12/24. Fares are subject to change and may not be available on all flights or dates of travel.
POS — CHI
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
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 September 16, 2025.

Round-trip from

$452
(Priceline)

One-way from

$314
(United Airlines)
From Trinidad and Tobago to Chicago (CHI)
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One-way flight 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 September 16, 2025.

This Priceline deal was found by Cheapflights users on 9/14. 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.
Tue 10/281:15 amPOS - ORD
2 stops43h 45mAir Canada
Wed 11/58:15 pmORD - POS
1 stop26h 55mAir Canada
Deal found 9/14$452
This Kiwi.com deal was found by Cheapflights users on 9/14. 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.
Wed 10/292:27 pmPOS - ORD
2 stops19h 55mMultiple Airlines
Wed 11/55:59 pmORD - POS
1 stop24h 01mMultiple Airlines
Deal found 9/14$463
This Copa Airlines deal was found by Cheapflights users on 9/14. 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.
Tue 10/283:51 amPOS - ORD
1 stop10h 50mCopa Airlines
Wed 11/56:56 amORD - POS
1 stop16h 52mCopa Airlines
Deal found 9/14$562
This American Airlines deal was found by Cheapflights users on 9/15. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/144:33 pmPOS - ORD
1 stop10h 04mAmerican Airlines
Sat 12/205:00 amORD - POS
1 stop16h 46mAmerican Airlines
Deal found 9/15$1,128

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 September 16, 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 10/28

1:15 am-8:00 pm

2 stops43h 45m

Chicago O'Hare Intl

Wed 11/5

8:15 pm-1:10 am

1 stop26h 55m

$452

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 10/29

2:27 pm-9:22 am

2 stops19h 55m

Chicago O'Hare Intl

Wed 11/5

5:59 pm-8:00 pm

1 stop24h 01m

$463

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 10/28

3:51 am-1:41 pm

1 stop10h 50m

Chicago O'Hare Intl

Wed 11/5

6:56 am-1:48 am

1 stop16h 52m

$562

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 2/26

1:30 am-11:09 am

1 stop11h 39m

Chicago O'Hare Intl

Tue 3/3

7:35 am-12:23 am

1 stop14h 48m

$574

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 2/26

2:15 am-5:48 pm

1 stop17h 33m

Chicago O'Hare Intl

Tue 3/3

7:15 am-1:10 am

2 stops15h 55m

$640

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 2/27

2:33 pm-12:31 pm

1 stop23h 58m

Chicago O'Hare Intl

Tue 3/3

6:56 am-1:15 pm

1 stop28h 19m

$653

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 12/25

6:02 am-4:12 pm

1 stop12h 10m

$314

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 12/24

2:20 am-12:05 pm

1 stop11h 45m

$314

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 12/25

7:40 am-9:10 am

3 stops27h 30m

$425

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 2/18

2:33 pm-12:04 am

1 stop11h 31m

$723

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 11 results
1
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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 September 16, 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 September 16, 2025.
Read reviews from past customers who have flown United Airlines and American Airlines 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.
United Airlines
7.4
Good
8,924 reviews

Comfort

7.3

Entertainment

7.1

Crew

8.1

Overall

7.4

Boarding

7.7

Food

6.6

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

FRA - SFO

Lufthansa was amazing, I wish United States based airlines operated like them.
United Airlines
7.4
Good
8,924 reviews
United Airlines
7.4
Good
8,924 reviews

Comfort

7.3

Entertainment

7.1

Crew

8.1

Overall

7.4

Boarding

7.7

Food

6.6

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

FRA - SFO

Lufthansa was amazing, I wish United States based airlines operated like them.
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,924 reviews

Comfort

7.3

Entertainment

7.1

Crew

8.1

Overall

7.4

Boarding

7.7

Food

6.6

Reviews

1 / 20
10.0
Excellent

Anonymous,Sep 2025

FRA - SFO

Lufthansa was amazing, I wish United States based airlines operated like them.

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.

  • How long is the flight from Trinidad and Tobago to Chicago?

    Airlines like Air Canada fly from Trinidad and Tobago to Chicago in about 43h 45m. The time it takes to get you to your destination can typically vary by up to . The distance between Trinidad and Tobago and Chicago is about 2697 mi.

  • 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
Chesterton

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Alternative routes for Trinidad and Tobago to Chicago

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 and Tobago to Chicago

Discover the top 3 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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Copa AirlinesCheapest$304Average$543FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$559Average$581FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$561Average$662FlexibilityNo cancel feeOn-time71%

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