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$243+ 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 9/15. Fares are subject to change and may not be available on all flights or dates of travel.
POS — CHI
Aug 25 — Sep 11
Mon 8/25
Mon 9/1
1 adult, Economy
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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 August 20, 2025.

Round-trip from

$453
(Kiwi.com)

One-way from

$243
(Trip.com)
From Trinidad to Chicago (CHI)
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One-way flight from Trinidad to Chicago (CHI)
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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 August 20, 2025.

This Kiwi.com deal was found by Cheapflights users on 8/17. 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.
Wed 10/159:10 amPOS - ORD
1 stop25h 12mMultiple Airlines
Sun 10/2610:27 amORD - POS
1 stop16h 48mMultiple Airlines
Deal found 8/17$453
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 9/39:10 amPOS - ORD
2 stops29h 02mMultiple Airlines
Wed 9/1010:27 amORD - POS
1 stop31h 28mMultiple Airlines
Deal found 8/18$469
This Copa Airlines deal was found by Cheapflights users on 8/18. 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.
Thu 12/113:47 amPOS - ORD
1 stop10h 59mCopa Airlines
Sat 1/172:13 pmORD - POS
1 stop9h 31mCopa Airlines
Deal found 8/18$562
This United Airlines deal was found by Cheapflights users on 8/17. 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.
Tue 10/1412:30 amPOS - ORD
1 stop24h 44mUnited Airlines
Sun 10/269:08 pmORD - POS
1 stop25h 15mUnited Airlines
Deal found 8/17$575
This American Airlines deal was found by Cheapflights users on 8/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/157:00 amPOS - ORD
2 stops15h 10mAmerican Airlines
Sun 10/268:45 amORD - POS
2 stops11h 35mAmerican Airlines
Deal found 8/17$578
This Air Canada deal was found by Cheapflights users on 8/18. 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.
Thu 12/112:15 amPOS - ORD
2 stops42h 40mAir Canada
Sat 1/173:55 pmORD - POS
1 stop31h 15mAir Canada
Deal found 8/18$584

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 August 20, 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 10/15

9:10 am-9:22 am

1 stop25h 12m

Chicago O'Hare Intl

Sun 10/26

10:27 am-4:15 am

1 stop16h 48m

$453

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 9/3

9:10 am-1:12 pm

2 stops29h 02m

Chicago O'Hare Intl

Wed 9/10

10:27 am-6:55 pm

1 stop31h 28m

$469

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 12/11

3:47 am-12:46 pm

1 stop10h 59m

Chicago O'Hare Intl

Sat 1/17

2:13 pm-1:44 am

1 stop9h 31m

$562

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 10/14

12:30 am-12:14 am

1 stop24h 44m

Chicago O'Hare Intl

Sun 10/26

9:08 pm-11:23 pm

1 stop25h 15m

$575

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 12/12

7:10 am-9:32 pm

1 stop16h 22m

Chicago O'Hare Intl

Sat 1/17

8:05 am-10:20 pm

2 stops12h 15m

$578

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Mon 9/15

10:10 am-10:48 pm

1 stop13h 38m

$243

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 9/14

2:25 am-10:53 am

1 stop9h 28m

$310

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Mon 2/16

3:40 am-12:30 pm

2 stops34h 50m

$313

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/18

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, August is the cheapest month in which you can book a flight from Trinidad to Chicago (average of $245). Flying from Trinidad 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 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 August 20, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Trinidad 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 August 20, 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
8,928 reviews

Comfort

7.3

Food

6.6

Boarding

7.7

Overall

7.4

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Thomas,Apr 2025

TPE - SFO

The boarding experience was okay. The dietary food choices were limited, the midway snacks were hard and dry. The seat was uncomfortable - stiff seat cushion, seat back kept springing back to the upright position, narrow seat width. Love the app and the ability to track my luggage. Flight crew was efficient.
United Airlines
7.4
Good
8,928 reviews
United Airlines
7.4
Good
8,928 reviews

Comfort

7.3

Food

6.6

Boarding

7.7

Overall

7.4

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Thomas,Apr 2025

TPE - SFO

The boarding experience was okay. The dietary food choices were limited, the midway snacks were hard and dry. The seat was uncomfortable - stiff seat cushion, seat back kept springing back to the upright position, narrow seat width. Love the app and the ability to track my luggage. Flight crew was efficient.
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,928 reviews

Comfort

7.3

Food

6.6

Boarding

7.7

Overall

7.4

Crew

8.1

Entertainment

7.1

Reviews

1 / 20
4.0
Okay

Thomas,Apr 2025

TPE - SFO

The boarding experience was okay. The dietary food choices were limited, the midway snacks were hard and dry. The seat was uncomfortable - stiff seat cushion, seat back kept springing back to the upright position, narrow seat width. Love the app and the ability to track my luggage. Flight crew was efficient.

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, August is the cheapest month in which you can book a flight from Trinidad to Chicago (average of $245). Flying from Trinidad 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 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 2 airlines flying from Trinidad to Chicago

Discover the top 2 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 August 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$505Average$581FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$561Average$662FlexibilityNo cancel feeOn-time71%

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