HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$444+ 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 2/12. Fares are subject to change and may not be available on all flights or dates of travel.
POS — CHI
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
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.

Cheap 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 December 18, 2025.

This Priceline deal was found by Cheapflights users on 12/16. 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.
Thu 12/252:15 amPOS - ORD
1 stop12h 46mAir Canada
Tue 12/302:00 pmORD - POS
1 stop9h 10mAir Canada
Deal found 12/16$669
This Gotogate deal was found by Cheapflights users on 12/16. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/252:15 amPOS - ORD
2 stops19h 55mMultiple Airlines
Tue 12/308:30 pmORD - POS
2 stops20h 55mMultiple Airlines
Deal found 12/16$758
This United Airlines deal was found by Cheapflights users on 12/16. 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.
Wed 12/171:30 amPOS - ORD
1 stop15h 10mUnited Airlines
Tue 12/237:35 amORD - POS
1 stop14h 48mUnited Airlines
Deal found 12/16$1,001
This Kiwi.com deal was found by Cheapflights users on 12/17. 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
Tue 12/237:01 pmORD - POS
2 stops29h 12mMultiple Airlines
Deal found 12/17$1,025
This Expedia deal was found by Cheapflights users on 12/17. 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.
Sun 12/213:55 pmPOS - ORD
2 stops28h 51mJetBlue
Tue 12/237:41 pmORD - POS
2 stops16h 49mJetBlue
Deal found 12/17$1,057
This United Airlines deal was found by Cheapflights users on 12/17. 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 12/202:20 amPOS - ORD
1 stop11h 45mUnited Airlines
Tue 12/231:37 pmORD - POS
1 stop9h 28mUnited Airlines
Deal found 12/17$1,085
This American Airlines deal was found by Cheapflights users on 12/16. 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.
Thu 12/186:02 amPOS - ORD
2 stops13h 47mAmerican Airlines
Tue 12/237:11 amORD - POS
2 stops14h 35mAmerican Airlines
Deal found 12/16$1,630

Find 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 December 18, 2025.

Round-trip from

$444
(Expedia)
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 December 18, 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

Thu 2/12

8:50 am-11:10 pm

1 stop16h 20m

Chicago O'Hare Intl

Thu 2/19

10:00 am-7:17 am

2 stops19h 17m

$444

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 1/30

8:20 am-5:43 pm

2 stops35h 23m

Chicago O'Hare Intl

Fri 2/6

10:00 am-1:20 am

1 stop13h 20m

$478

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 2/12

12:22 pm-11:10 pm

1 stop12h 48m

Chicago O'Hare Intl

Thu 2/19

2:00 pm-1:20 am

1 stop9h 20m

$480

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 1/29

2:20 am-3:10 pm

1 stop14h 50m

Chicago O'Hare Intl

Fri 2/6

10:00 am-1:20 am

1 stop13h 20m

$513

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 2/1

8:20 am-6:32 pm

1 stop12h 12m

Chicago O'Hare Intl

Sun 2/8

10:00 am-1:20 am

1 stop13h 20m

$529

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 5/6

2:22 pm-1:15 am

1 stop11h 53m

Chicago O'Hare Intl

Sun 5/10

8:02 am-1:46 am

1 stop16h 44m

$584

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 5/6

3:10 pm-8:49 am

2 stops18h 39m

Chicago O'Hare Intl

Sun 5/10

7:17 pm-2:00 pm

1 stop17h 43m

$640

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

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 December 18, 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 December 18, 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
9,091 reviews

Crew

8.1

Comfort

7.3

Entertainment

7.1

Food

6.6

Overall

7.4

Boarding

7.7

Reviews

1 / 20
4.0
Okay

Kevin,Dec 2025

BOS - EWR

Seems like every United flight has a delay and it’s always someone else’s fault. Step up and take some accountability
United Airlines
7.4
Good
9,091 reviews
United Airlines
7.4
Good
9,091 reviews

Crew

8.1

Comfort

7.3

Entertainment

7.1

Food

6.6

Overall

7.4

Boarding

7.7

Reviews

1 / 20
4.0
Okay

Kevin,Dec 2025

BOS - EWR

Seems like every United flight has a delay and it’s always someone else’s fault. Step up and take some accountability
American Airlines
7.2
Good
11,054 reviews
United Airlines
7.4
Good
9,091 reviews

Crew

8.1

Comfort

7.3

Entertainment

7.1

Food

6.6

Overall

7.4

Boarding

7.7

Reviews

1 / 20
4.0
Okay

Kevin,Dec 2025

BOS - EWR

Seems like every United flight has a delay and it’s always someone else’s fault. Step up and take some accountability

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 JetBlue and Air Canada fly from Trinidad and Tobago to Chicago in about 16h 20m. The time it takes to get you to your destination can typically vary by up to 2h 15m. 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
Lansing
Merrillville
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
Nassau to O'Hare Intl flights
Luis Munoz Marin Intl to St. Louis flights
Santo Domingo to O'Hare Intl flights
Oranjestad to O'Hare Intl flights
Saint Thomas Island to O'Hare Intl flights
Willemstad to O'Hare Intl flights
Santo Domingo to Midway flights
Kingston to O'Hare Intl flights
Nassau to Midway flights
Christiansted to O'Hare Intl flights
Simpson Bay to O'Hare Intl flights
Montego Bay to O'Hare Intl flights
Santiago de los Caballeros to O'Hare Intl flights
Port of Spain to O'Hare Intl flights
Saint Thomas Island to St. Louis flights
George Town to O'Hare Intl flights
Nassau to St. Louis flights
Port of Spain to St. Louis flights
Aguadilla to O'Hare Intl flights
Montego Bay to Midway flights
Road Town to O'Hare Intl flights
Bridgetown to O'Hare Intl flights
Oranjestad to St. Louis flights
Aguadilla to Midway flights
St. George's to St. Louis flights
Vieques to O'Hare Intl flights
Port Au Prince to Midway flights
Simpson Bay to Midway flights
St. John's to O'Hare Intl flights
Culebra to O'Hare Intl flights
Port Au Prince to O'Hare Intl flights
Roseau to O'Hare Intl 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
Copa AirlinesCheapest$299Average$542FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$474Average$579FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$562Average$698FlexibilityNo 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.