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$235+ 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 7/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — POS
juin 17 — juin 241
mar. 6/17
mar. 6/24
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 juin 12, 2025.

Round-trip from

$503
(Booking.com)

One-way from

$235
(Air Canada)

Popular in

February

Cheapest in

January

Average price

$658
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. 18% potential increase in price ($165 potential increase over avg. RT price).
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Cheapest flight prices on average. 9% potential price decrease ($62 potential savings vs. average RT price).
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Average for round-trip flights in June 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 juin 12, 2025.

This Booking.com deal was found by Cheapflights users on 6/11. 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.
sam. 7/268:25 pmORD - POS
1 stop27h 55mAir Canada
ven. 8/12:20 amPOS - ORD
2 stops17h 33mAir Canada
Deal found 6/11$503
This Copa Airlines deal was found by Cheapflights users on 6/10. 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.
mer. 10/223:07 pmORD - POS
1 stop9h 41mCopa Airlines
dim. 10/264:01 amPOS - ORD
1 stop10h 41mCopa Airlines
Deal found 6/10$511
This JetBlue deal was found by Cheapflights users on 6/11. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sam. 7/266:16 amORD - POS
1 stop10h 48mJetBlue
sam. 8/28:50 amPOS - ORD
1 stop14h 38mJetBlue
Deal found 6/11$523
This American Airlines deal was found by Cheapflights users on 6/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 7/145:00 amORD - POS
1 stop8h 00mAmerican Airlines
mar. 8/267:00 amPOS - ORD
1 stop11h 55mAmerican Airlines
Deal found 6/12$548
This Booking.com deal was found by Cheapflights users on 6/12. 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.
ven. 9/129:55 amORD - POS
1 stop14h 30mMultiple Airlines
ven. 9/1910:10 amPOS - ORD
1 stop29h 24mMultiple Airlines
Deal found 6/12$565
This Trip.com deal was found by Cheapflights users on 6/12. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven. 9/128:45 amORD - POS
1 stop13h 38mUnited Airlines
jeu. 9/1812:30 amPOS - ORD
1 stop20h 28mUnited Airlines
Deal found 6/12$620

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 juin 12, 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

sam. 7/26

8:25 pm-1:20 am

1 stop27h 55m

Port of Spain Piarco Intl

ven. 8/1

2:20 am-6:53 pm

2 stops17h 33m

$503

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

mer. 10/22

3:07 pm-1:48 am

1 stop9h 41m

Port of Spain Piarco Intl

dim. 10/26

4:01 am-1:42 pm

1 stop10h 41m

$511

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

sam. 7/26

6:16 am-6:04 pm

1 stop10h 48m

Port of Spain Piarco Intl

sam. 8/2

8:50 am-10:28 pm

1 stop14h 38m

$523

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

lun. 7/14

5:00 am-2:00 pm

1 stop8h 00m

Port of Spain Piarco Intl

mar. 8/26

7:00 am-5:55 pm

1 stop11h 55m

$548

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

ven. 9/12

9:55 am-1:25 am

1 stop14h 30m

Port of Spain Piarco Intl

ven. 9/19

10:10 am-2:34 pm

1 stop29h 24m

$565

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

ven. 9/12

8:45 am-11:23 pm

1 stop13h 38m

Port of Spain Piarco Intl

jeu. 9/18

12:30 am-7:58 pm

1 stop20h 28m

$620

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

ven. 7/25

3:50 pm-1:20 am

1 stop8h 30m

$235

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

dim. 7/27

6:16 am-6:04 pm

1 stop10h 48m

$347

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

ven. 7/25

4:37 pm-2:30 pm

3 stops20h 53m

$351

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

dim. 7/27

4:45 pm-11:23 pm

2 stops29h 38m

$1,269

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

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 juin 12, 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.

Rainfall in Trinidad by month

Plan your trip to Trinidad by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Trinidad ranges from 1.2 - 9.8 inches per month. June is typically the wettest month, when rainfall can reach 9.8 in. March is typically the driest time to visit Trinidad when rainfall is around 1.2 in.

Temperature in Trinidad by month

Plan your trip to Trinidad by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Trinidad, use this chart to help with planning. For those seeking warmer temperatures, April is the ideal time of year to visit, when temperatures reach an average of 80.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 juin 12, 2025.
See what other customers who have flown with Copa Airlines, United Airlines and JetBlue from Chicago to Trinidad have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Copa Airlines
7.5
Good
1,451 reviews

Boarding

7.8

Comfort

7.4

Entertainment

6.8

Overall

7.5

Food

6.8

Crew

8.1

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.
Copa Airlines
7.5
Good
1,451 reviews
Copa Airlines
7.5
Good
1,451 reviews

Boarding

7.8

Comfort

7.4

Entertainment

6.8

Overall

7.5

Food

6.8

Crew

8.1

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.
United Airlines
7.4
Good
8,790 reviews
Copa Airlines
7.5
Good
1,451 reviews

Boarding

7.8

Comfort

7.4

Entertainment

6.8

Overall

7.5

Food

6.8

Crew

8.1

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.
JetBlue
7.3
Good
2,925 reviews
Copa Airlines
7.5
Good
1,451 reviews

Boarding

7.8

Comfort

7.4

Entertainment

6.8

Overall

7.5

Food

6.8

Crew

8.1

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.
American Airlines
7.2
Good
10,000 reviews
Copa Airlines
7.5
Good
1,451 reviews

Boarding

7.8

Comfort

7.4

Entertainment

6.8

Overall

7.5

Food

6.8

Crew

8.1

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.
Air Canada
7.1
Good
9,537 reviews
Copa Airlines
7.5
Good
1,451 reviews

Boarding

7.8

Comfort

7.4

Entertainment

6.8

Overall

7.5

Food

6.8

Crew

8.1

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.

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.

  • What are the cheapest airlines to fly from Chicago to Trinidad one-way?

    To fly one-way, consider booking your trip with Air Canada, which is currently one of the cheapest options available, starting at $235. JetBlue flights start at $347 while deals on United Airlines start at $1,269 one-way.

  • 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
St. Louis to Port of Spain flights
O'Hare Intl to Scarborough 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 juin 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$480Average$628FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$487Average$634FlexibilityNo cancel feeOn-time71%

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