HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$457+ Cheap flights from Trinidad 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 10/19. Fares are subject to change and may not be available on all flights or dates of travel.
POS — CHI
Nov 13 — Nov 201
Thu 11/13
Thu 11/20
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Trinidad 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 to Chicago

Keep the following information in mind while searching for Trinidad to Chicago flight deals. Data was last updated October 14, 2025.

Round-trip from

$463
(Gotogate)
From Trinidad to Chicago (CHI)
Search Deals

Find flight deals from Trinidad to Chicago

Cheapest flights from Trinidad to Chicago
Explore the most affordable flight options available from Trinidad to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 14, 2025.

This Air Canada deal was found by Cheapflights users on 10/14. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/192:25 amPOS - ORD
2 stops17h 29mAir Canada
Fri 10/242:00 pmORD - POS
1 stop10h 20mAir Canada
Deal found 10/14$457
This Booking.com deal was found by Cheapflights users on 10/12. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/132:25 amPOS - ORD
1 stop31h 44mAir Canada
Sat 11/88:15 pmORD - POS
1 stop26h 55mAir Canada
Deal found 10/12$463
This Mytrip deal was found by Cheapflights users on 10/13. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/242:25 amPOS - ORD
1 stop17h 59mMultiple Airlines
Mon 11/175:10 amORD - POS
1 stop12h 50mMultiple Airlines
Deal found 10/13$469
This Kiwi.com deal was found by Cheapflights users on 10/12. 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.
Fri 11/149:10 amPOS - ORD
1 stop26h 37mMultiple Airlines
Wed 11/263:43 pmORD - POS
1 stop26h 17mMultiple Airlines
Deal found 10/12$477
This Booking.com deal was found by Cheapflights users on 10/12. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/132:15 amPOS - ORD
1 stop19h 15mAir Canada
Wed 11/268:15 pmORD - POS
1 stop26h 55mAir Canada
Deal found 10/12$482
This Kiwi.com deal was found by Cheapflights users on 10/12. 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.
Sat 10/259:10 amPOS - ORD
2 stops25h 26mMultiple Airlines
Wed 11/193:26 pmORD - POS
1 stop26h 34mMultiple Airlines
Deal found 10/12$498

Cheapflights Fare Finder

 
Customize your flight search to find flights from Trinidad 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 14, 2025.
Use the filters below to find and compare flights from Trinidad to Chicago that are best for you.

Fly from

Trinidad

Fly to

Chicago

Route

Depart

Return

Price

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 10/24

2:25 am-6:54 pm

2 stops17h 29m

Chicago O'Hare Intl

Wed 11/19

8:15 pm-1:10 am

1 stop26h 55m

$463

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 11/14

9:10 am-9:47 am

1 stop26h 37m

Chicago O'Hare Intl

Wed 11/26

3:43 pm-8:00 pm

1 stop26h 17m

$477

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 11/13

2:15 am-7:30 pm

1 stop19h 15m

Chicago O'Hare Intl

Wed 11/26

8:15 pm-1:10 am

1 stop26h 55m

$482

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 10/24

2:25 am-5:05 pm

2 stops15h 40m

Chicago O'Hare Intl

Mon 11/17

5:10 am-8:00 pm

1 stop12h 50m

$521

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 10/24

2:25 am-8:06 pm

2 stops18h 41m

Chicago O'Hare Intl

Wed 11/19

3:26 pm-6:55 pm

3 stops25h 29m

$537

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 2/26

2:15 am-3:10 pm

1 stop14h 55m

Chicago O'Hare Intl

Tue 3/3

10:00 am-1:10 am

1 stop13h 10m

$539

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/12

Best time to book a flight from Trinidad to Chicago

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

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

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

Find hourly flight availability from Trinidad 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 14, 2025.

A simple way to save on the total cost of your ticket is to fly from Trinidad to Chicago at noon. If you’re flexible enough to do this you can expect to save up to 19% on your trip compared to booking a flight in the afternoon.

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 14, 2025.
Read through reviews of airlines operating flights from Trinidad to Chicago, such as United Airlines and American Airlines. 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
8,976 reviews

Entertainment

7.1

Overall

7.4

Food

6.6

Comfort

7.3

Crew

8.1

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
United Airlines
7.4
Good
8,976 reviews
United Airlines
7.4
Good
8,976 reviews

Entertainment

7.1

Overall

7.4

Food

6.6

Comfort

7.3

Crew

8.1

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.
American Airlines
7.2
Good
11,042 reviews
United Airlines
7.4
Good
8,976 reviews

Entertainment

7.1

Overall

7.4

Food

6.6

Comfort

7.3

Crew

8.1

Boarding

7.7

Reviews

1 / 20
8.0
Excellent

Anonymous,Oct 2025

YUL - ORD

Crew and customer service are 5 stars. I had a lot of luggage for a very long trip and they were nothing but helpful and found solutions to every problem. It was my first time flying with United, and they really are the friendly skies. Leg room however, on 2/3 flights was terrible. Same for entertainment: There was only a seat-mounted screen on 1/3 flights. It would have been nice to have on the longest leg of the journey.

Related info for your journey

Find useful and relevant information for your journey from Trinidad 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 to Chicago?

    Departing from Trinidad to Chicago will take you 17h 29m. The distance between Trinidad and Chicago is about 2697 mi.

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

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

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

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Trinidad to Chicago.

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

    Yes. Cheapflights offers flight deals from Trinidad 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 to Chicago?

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

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 to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Port of Spain to O'Hare Intl flights
Port of Spain to St. Louis flights

Top 3 airlines flying from Trinidad to Chicago

Discover the top 3 airlines that operate flights from Trinidad 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 14, 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.