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$265+ Cheap flights from Trinidad 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 5/9. Fares are subject to change and may not be available on all flights or dates of travel.
POS — CHI
Jan 6 — Jan 131
Tue 1/6
Tue 1/13
1 adult, Economy
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Cheap 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 December 7, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/7. 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 12/319:10 amPOS - ORD
2 stops27h 30mMultiple Airlines
Wed 1/76:05 pmORD - POS
1 stop22h 50mMultiple Airlines
Deal found 12/7$536
This Kiwi.com deal was found by Cheapflights users on 12/7. 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 12/319:10 amPOS - ORD
2 stops27h 30mMultiple Airlines
Sun 1/116:57 pmORD - POS
1 stop21h 58mMultiple Airlines
Deal found 12/7$557
This Kiwi.com deal was found by Cheapflights users on 12/7. 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 12/319:10 amPOS - ORD
1 stop9h 50mMultiple Airlines
Mon 1/126:57 pmORD - POS
1 stop21h 58mMultiple Airlines
Deal found 12/7$559
This Kiwi.com deal was found by Cheapflights users on 12/7. 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 12/319:10 amPOS - ORD
1 stop9h 50mMultiple Airlines
Thu 1/86:57 pmORD - POS
1 stop21h 58mMultiple Airlines
Deal found 12/7$579
This Kiwi.com deal was found by Cheapflights users on 12/7. 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 12/319:10 amPOS - ORD
2 stops27h 30mMultiple Airlines
Fri 1/96:57 pmORD - POS
1 stop21h 58mMultiple Airlines
Deal found 12/7$600
This Kiwi.com deal was found by Cheapflights users on 12/7. 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 12/319:10 amPOS - ORD
2 stops27h 30mMultiple Airlines
Sat 1/106:57 pmORD - POS
1 stop21h 58mMultiple Airlines
Deal found 12/7$611
This Air Canada deal was found by Cheapflights users on 12/6. 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 12/232:15 amPOS - ORD
2 stops42h 38mAir Canada
Wed 12/318:30 pmORD - POS
1 stop26h 50mAir Canada
Deal found 12/6$651
This Kiwi.com deal was found by Cheapflights users on 12/6. 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 12/2110:10 amPOS - ORD
1 stop16h 16mMultiple Airlines
Wed 12/317:20 amORD - POS
2 stops16h 28mMultiple Airlines
Deal found 12/6$699
This Kiwi.com deal was found by Cheapflights users on 12/4. 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 12/179:10 amPOS - ORD
1 stop11h 26mMultiple Airlines
Sat 12/277:57 pmORD - POS
2 stops31h 18mMultiple Airlines
Deal found 12/4$717

Find flight deals from Trinidad to Chicago

Keep the following information in mind while searching for Trinidad to Chicago flight deals. Data was last updated December 7, 2025.

Round-trip from

$536
(Kiwi.com)

One-way from

$265
(Orbitz)
From Trinidad to Chicago (CHI)
Search Deals
One-way flight from Trinidad to Chicago (CHI)
Search Deals

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 December 7, 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

Wed 12/31

9:10 am-10:40 am

2 stops27h 30m

Chicago O'Hare Intl

Tue 1/13

9:23 am-6:55 pm

1 stop31h 32m

$536

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 12/31

9:10 am-10:40 am

2 stops27h 30m

Chicago O'Hare Intl

Thu 1/8

6:57 pm-6:55 pm

1 stop21h 58m

$557

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 1/7

9:10 am-8:18 am

1 stop25h 08m

Chicago O'Hare Intl

Tue 1/13

5:57 pm-6:55 pm

2 stops22h 58m

$567

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 1/7

9:10 am-8:18 am

1 stop25h 08m

Chicago O'Hare Intl

Wed 1/14

5:57 pm-6:55 pm

2 stops22h 58m

$568

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

3:21 pm-1:46 am

1 stop9h 25m

$584

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 5/6

3:10 pm-7:10 am

2 stops17h 00m

Chicago O'Hare Intl

Sun 5/10

5:00 am-2:00 pm

1 stop8h 00m

$640

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 1/1

10:10 am-12:30 am

1 stop16h 20m

Chicago O'Hare Intl

Mon 1/12

6:57 pm-6:55 pm

1 stop21h 58m

$641

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 12/23

2:15 am-6:53 pm

2 stops42h 38m

Chicago O'Hare Intl

Wed 12/31

6:00 pm-1:20 am

2 stops29h 20m

$651

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 1/1

10:10 am-12:30 am

1 stop16h 20m

Chicago O'Hare Intl

Tue 1/13

5:57 pm-6:55 pm

2 stops22h 58m

$654

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sat 5/9

2:35 am-10:53 am

1 stop9h 18m

$265

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/5

Showing 1-10 of 14 results
1
2

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 December 7, 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 December 7, 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
9,072 reviews

Food

6.6

Boarding

7.7

Crew

8.1

Entertainment

7.1

Comfort

7.3

Overall

7.4

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
9,072 reviews
United Airlines
7.4
Good
9,072 reviews

Food

6.6

Boarding

7.7

Crew

8.1

Entertainment

7.1

Comfort

7.3

Overall

7.4

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
11,046 reviews
United Airlines
7.4
Good
9,072 reviews

Food

6.6

Boarding

7.7

Crew

8.1

Entertainment

7.1

Comfort

7.3

Overall

7.4

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.

  • 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
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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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 St. Louis flights
Port of Spain to O'Hare Intl 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 December 7, 2025.
AirlineCheapestAverageFlexibilityOn-time
Copa AirlinesCheapest$299Average$542FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$559Average$579FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$562Average$698FlexibilityNo cancel feeOn-time71%

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