HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$439+ 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 1/5. Fares are subject to change and may not be available on all flights or dates of travel.
POS — CHI
Nov 30 — Dec 71
Sun 11/30
Sun 12/7
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Trinidad and Tobago to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 October 31, 2025.

This Air Canada deal was found by Cheapflights users on 10/30. 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 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 10/30$471
This United Airlines deal was found by Cheapflights users on 10/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/201:30 amPOS - ORD
1 stop23h 07mUnited Airlines
Thu 1/12:37 pmORD - POS
1 stop8h 28mUnited Airlines
Deal found 10/29$571
This American Airlines deal was found by Cheapflights users on 10/30. 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 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 stop17h 40mAmerican Airlines
Sun 11/3012:19 amORD - POS
1 stop13h 11mAmerican Airlines
Deal found 10/30$574
This American Airlines deal was found by Cheapflights users on 10/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/234:30 pmPOS - ORD
1 stop18h 35mAmerican Airlines
Sun 11/307:17 pmORD - POS
1 stop18h 13mAmerican Airlines
Deal found 10/30$580
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Sun 12/217:35 pmPOS - ORD
1 stop23h 25mMultiple Airlines
Wed 12/317:30 amORD - POS
2 stops16h 18mMultiple Airlines
Deal found 10/29$581
This United Airlines deal was found by Cheapflights users on 10/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/221:30 amPOS - ORD
1 stop32h 11mUnited Airlines
Sun 11/3011:55 pmORD - POS
1 stop22h 28mUnited Airlines
Deal found 10/30$593
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Sun 12/217:35 pmPOS - ORD
1 stop23h 25mMultiple Airlines
Sat 1/35:45 amORD - POS
2 stops12h 35mMultiple Airlines
Deal found 10/29$598
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Sun 12/219:10 amPOS - ORD
1 stop9h 50mMultiple Airlines
Thu 1/17:20 amORD - POS
2 stops27h 51mMultiple Airlines
Deal found 10/29$617
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Sun 12/219:10 amPOS - ORD
1 stop9h 50mMultiple Airlines
Tue 12/307:30 amORD - POS
2 stops28h 01mMultiple Airlines
Deal found 10/29$639

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 October 31, 2025.

Round-trip from

$471
(Air Canada)

One-way from

$439
(Kiwi.com)
From Trinidad and Tobago to Chicago (CHI)
Search Deals
One-way flight from Trinidad and Tobago to Chicago (CHI)
Search Deals

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 October 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 11/25

2:15 am-1:01 pm

1 stop12h 46m

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

2:15 am-6:52 pm

2 stops42h 37m

Chicago O'Hare Intl

Tue 3/3

10:00 am-1:10 am

1 stop13h 10m

$483

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sat 12/20

1:30 am-10:37 pm

1 stop23h 07m

Chicago O'Hare Intl

Wed 12/31

8:54 am-12:23 am

1 stop13h 29m

$571

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sat 12/20

1:30 am-10:37 pm

1 stop23h 07m

Chicago O'Hare Intl

Thu 1/1

2:37 pm-1:05 am

1 stop8h 28m

$571

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 11/26

7:19 am-10:59 pm

1 stop17h 40m

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 2/26

1:30 am-12:37 pm

1 stop13h 07m

Chicago O'Hare Intl

Tue 3/3

2:30 pm-1:05 am

1 stop8h 35m

$574

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 11/23

4:30 pm-9:05 am

1 stop18h 35m

Chicago O'Hare Intl

Sun 11/30

7:17 pm-3:30 pm

1 stop18h 13m

$580

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Mon 1/5

3:40 am-5:00 pm

2 stops39h 20m

$439

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 1/6

4:30 pm-9:05 am

1 stop18h 35m

$463

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Mon 1/5

2:20 am-10:53 am

1 stop10h 33m

$503

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

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, December is the cheapest month in which you can book a flight from Trinidad and Tobago to Chicago (average of $304). Flying from Trinidad and Tobago to Chicago 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 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 October 31, 2025.

One of the essential ways to save on airfare from Trinidad and Tobago to Chicago is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight at noon could potentially save you up to 19% on airfare.

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 October 31, 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
8,998 reviews

Overall

7.4

Boarding

7.7

Comfort

7.3

Crew

8.1

Food

6.6

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
United Airlines
7.4
Good
8,998 reviews
United Airlines
7.4
Good
8,998 reviews

Overall

7.4

Boarding

7.7

Comfort

7.3

Crew

8.1

Food

6.6

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
American Airlines
7.2
Good
11,035 reviews
United Airlines
7.4
Good
8,998 reviews

Overall

7.4

Boarding

7.7

Comfort

7.3

Crew

8.1

Food

6.6

Entertainment

7.1

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000

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 and United Airlines fly from Trinidad and Tobago to Chicago in about 12h 46m. The time it takes to get you to your destination can typically vary by up to 10h 21m. The distance between Trinidad and Tobago and Chicago is about 2697 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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, December is the cheapest month in which you can book a flight from Trinidad and Tobago to Chicago (average of $304). Flying from Trinidad and Tobago to Chicago 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?

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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Trinidad and Tobago to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Punta Cana to O'Hare Intl flights
Punta Cana to Midway flights
Luis Munoz Marin Intl to O'Hare Intl flights
Luis Munoz Marin Intl to Midway flights
Santo Domingo to O'Hare Intl flights
Luis Munoz Marin Intl to St. Louis flights
Oranjestad to O'Hare Intl flights
Nassau to O'Hare Intl flights
Santo Domingo to Midway flights
Montego Bay to O'Hare Intl flights
Willemstad to O'Hare Intl flights
Saint Thomas Island to O'Hare Intl flights
Nassau to Midway flights
Kingston to O'Hare Intl flights
Simpson Bay to O'Hare Intl flights
Santiago de los Caballeros to O'Hare Intl flights
George Town to O'Hare Intl flights
Port of Spain to O'Hare Intl flights
Christiansted to O'Hare Intl flights
Bridgetown to O'Hare Intl flights
Simpson Bay to Midway flights
Montego Bay to Midway flights
Roseau to O'Hare Intl flights
Aguadilla to O'Hare Intl flights
St. George's to St. Louis flights
Oranjestad to St. Louis flights
Vieques to O'Hare Intl flights
Nassau to St. Louis flights
Port of Spain to St. Louis flights
Saint Thomas Island to St. Louis flights
Port Au Prince to O'Hare Intl flights
Road Town to O'Hare Intl flights
Culebra to O'Hare Intl flights
St. John's to O'Hare Intl flights
Port Au Prince to Midway flights
Aguadilla to Midway flights

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 October 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Copa AirlinesCheapest$299Average$542FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$559Average$579FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$561Average$662FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.