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$189+ Cheap flights from Chicago (CHI) to Trinidad

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.
CHI — POS
Aug 25 — Sep 11
Mon 8/25
Mon 9/1
1 adult, Economy
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Cheap flight deals from Chicago to Trinidad

Keep the following information in mind while searching for Chicago to Trinidad flight deals. Data was last updated August 20, 2025.

Round-trip from

$408
(Trip.com)

One-way from

$189
(Kiwi.com)

Popular in

February

Cheapest in

January

Average price

$711
From Chicago (CHI) to Trinidad
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One-way flight from Chicago (CHI) to Trinidad
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Highest demand for flights based on searches. 17% potential increase in price ($152 potential increase over avg. RT price).
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Cheapest flight prices on average. 9% potential price decrease ($63 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Chicago to Trinidad

Cheapest flights from Chicago to Trinidad
Explore the most affordable flight options available from Chicago to Trinidad. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 20, 2025.

This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1810:27 amORD - POS
1 stop16h 48mMultiple Airlines
Sun 9/216:25 pmPOS - ORD
1 stop15h 53mMultiple Airlines
Deal found 8/18$408
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 9/195:05 amORD - POS
1 stop13h 55mMultiple Airlines
Mon 9/2910:10 amPOS - ORD
1 stop13h 38mMultiple Airlines
Deal found 8/19$458
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.
Sun 10/510:27 amORD - POS
1 stop16h 48mMultiple Airlines
Sat 10/259:10 amPOS - ORD
1 stop25h 12mMultiple Airlines
Deal found 8/17$461
This Kiwi.com deal was found by Cheapflights users on 8/19. 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.
Thu 9/1110:27 amORD - POS
1 stop16h 48mMultiple Airlines
Tue 9/239:10 amPOS - ORD
1 stop25h 08mMultiple Airlines
Deal found 8/19$462
This Kiwi.com deal was found by Cheapflights users on 8/20. 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 10/35:05 amORD - POS
1 stop13h 55mMultiple Airlines
Mon 10/69:10 amPOS - ORD
1 stop25h 12mMultiple Airlines
Deal found 8/20$473
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 10/227:29 pmORD - POS
2 stops29h 17mMultiple Airlines
Sun 10/266:25 pmPOS - ORD
1 stop15h 57mMultiple Airlines
Deal found 8/19$491

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Trinidad 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 Chicago to Trinidad that are best for you.

Fly from

Chicago

Fly to

Trinidad

Route

Depart

Return

Price

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 9/18

10:27 am-4:15 am

1 stop16h 48m

Port of Spain Piarco Intl

Sun 9/21

6:25 pm-9:18 am

1 stop15h 53m

$408

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 9/19

5:05 am-8:00 pm

1 stop13h 55m

Port of Spain Piarco Intl

Mon 9/29

10:10 am-10:48 pm

1 stop13h 38m

$458

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 10/5

10:27 am-4:15 am

1 stop16h 48m

Port of Spain Piarco Intl

Sat 10/25

9:10 am-9:22 am

1 stop25h 12m

$461

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 9/11

10:27 am-4:15 am

1 stop16h 48m

Port of Spain Piarco Intl

Tue 9/23

9:10 am-9:18 am

1 stop25h 08m

$462

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 10/3

5:05 am-8:00 pm

1 stop13h 55m

Port of Spain Piarco Intl

Mon 10/6

9:10 am-9:22 am

1 stop25h 12m

$473

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 9/15

5:05 am-8:00 pm

1 stop13h 55m

$189

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 11/15

6:40 am-1:55 pm

2 stops29h 15m

$221

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 11/15

8:15 pm-1:10 am

1 stop26h 55m

$238

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 12/17

8:15 pm-1:10 am

1 stop26h 55m

$388

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 12/17

7:00 am-10:15 pm

1 stop13h 15m

$553

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/20

Showing 1-10 of 11 results
1
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Best time to book a flight from Chicago to Trinidad

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

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

Currently, October is the cheapest month in which you can book a flight from Chicago to Trinidad (average of $435). Flying from Chicago to Trinidad in December is currently the most expensive (average of $710). 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 CHI to LAZ?

Find hourly flight availability from Chicago to Trinidad. 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 Chicago to Trinidad as you normally would.

Reviews of airlines servicing Trinidad

Get insights into the airlines that provide service to Trinidad. 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 Trinidad. Reviews last updated August 20, 2025.
Peruse reviews from past customers who have flown with United Airlines and American Airlines from Chicago to Trinidad to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,928 reviews

Overall

7.4

Food

6.6

Boarding

7.7

Crew

8.1

Entertainment

7.1

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??
United Airlines
7.4
Good
8,928 reviews
United Airlines
7.4
Good
8,928 reviews

Overall

7.4

Food

6.6

Boarding

7.7

Crew

8.1

Entertainment

7.1

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,928 reviews

Overall

7.4

Food

6.6

Boarding

7.7

Crew

8.1

Entertainment

7.1

Comfort

7.3

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??

Related info for your journey

Find useful and relevant information for your journey from Chicago to Trinidad. 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 Chicago to Trinidad that include hotel bookings?

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago to Trinidad 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 Chicago to Trinidad?

    Currently, October is the cheapest month in which you can book a flight from Chicago to Trinidad (average of $435). Flying from Chicago to Trinidad in December is currently the most expensive (average of $710). 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

Browse thousands of different options on Cheapflights for your next trip

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Alternative routes for Chicago to Trinidad

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

Top 2 airlines flying from Chicago to Trinidad

Discover the top 2 airlines that operate flights from Chicago to Trinidad. 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$480Average$626FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$487Average$610FlexibilityNo cancel feeOn-time71%

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