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Trinidad

$198+ 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 5/4. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — POS
Jan 6 — Jan 131
Tue 1/6
Tue 1/13
1 adult, Economy
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Cheap 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 December 7, 2025.

This Priceline deal was found by Cheapflights users on 12/5. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/68:30 pmORD - POS
1 stop26h 40mAir Canada
Thu 12/112:15 amPOS - ORD
1 stop14h 55mAir Canada
Deal found 12/5$443
This Mytrip deal was found by Cheapflights users on 12/5. 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.
Sat 12/64:38 pmORD - POS
3 stops30h 32mMultiple Airlines
Thu 12/112:15 amPOS - ORD
1 stop12h 46mMultiple Airlines
Deal found 12/5$616
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.
Fri 12/1910:12 amORD - POS
2 stops13h 36mMultiple Airlines
Thu 1/810:10 amPOS - ORD
1 stop12h 20mMultiple Airlines
Deal found 12/6$794
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 12/218:26 pmORD - POS
2 stops27h 22mMultiple Airlines
Thu 1/810:10 amPOS - ORD
1 stop12h 20mMultiple Airlines
Deal found 12/6$816
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.
Sat 12/206:40 amORD - POS
1 stop21h 30mMultiple Airlines
Thu 1/810:10 amPOS - ORD
1 stop12h 20mMultiple Airlines
Deal found 12/6$829
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/219:23 pmORD - POS
1 stop25h 00mUnited Airlines
Wed 1/71:30 amPOS - ORD
1 stop20h 20mUnited Airlines
Deal found 12/6$841
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/219:23 pmORD - POS
1 stop25h 00mUnited Airlines
Mon 1/51:30 amPOS - ORD
1 stop32h 17mUnited Airlines
Deal found 12/6$853
This United Airlines deal was found by Cheapflights users on 12/5. 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 12/169:05 pmORD - POS
1 stop25h 18mUnited Airlines
Mon 12/292:20 amPOS - ORD
1 stop11h 45mUnited Airlines
Deal found 12/5$862
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.
Fri 12/1910:12 amORD - POS
2 stops13h 36mMultiple Airlines
Wed 1/79:10 amPOS - ORD
1 stop25h 08mMultiple Airlines
Deal found 12/6$866

Find flight deals from Chicago to Trinidad

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

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$373
(Expedia)

One-way from

$198
(FlightHub)

Popular in

December

Cheapest in

October

Average price

$1,705
Provider with most accurate pricing for Chicago (CHI)-Port of Spain Piarco Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Port of Spain Piarco Intl flights.
Search Deals
From Chicago (CHI) to Trinidad
Search Deals
One-way flight from Chicago (CHI) to Trinidad
Search Deals
Highest demand for flights based on searches. 36% potential increase in price ($425 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 16% potential price decrease ($107 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 7, 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

Tue 3/3

10:00 am-7:17 am

2 stops19h 17m

Port of Spain Piarco Intl

Thu 3/12

3:26 pm-5:24 pm

2 stops26h 58m

$387

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 3/12

7:15 am-12:20 am

2 stops16h 05m

Port of Spain Piarco Intl

Tue 3/17

1:20 am-2:55 pm

2 stops14h 35m

$434

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 4/18

8:20 pm-12:20 am

1 stop27h 00m

Port of Spain Piarco Intl

Fri 4/24

1:20 am-1:00 pm

1 stop12h 40m

$442

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 4/17

2:00 pm-12:20 am

1 stop9h 20m

Port of Spain Piarco Intl

Thu 4/23

1:20 am-6:33 pm

2 stops18h 13m

$443

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 4/17

9:50 am-12:20 am

1 stop13h 30m

Port of Spain Piarco Intl

Fri 4/24

1:20 am-11:08 am

1 stop10h 48m

$443

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 4/19

2:00 pm-12:20 am

1 stop9h 20m

Port of Spain Piarco Intl

Thu 4/23

1:20 am-11:08 am

1 stop10h 48m

$443

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 3/13

10:00 am-12:20 am

1 stop13h 20m

Port of Spain Piarco Intl

Tue 3/17

1:20 am-3:10 pm

1 stop14h 50m

$450

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 5/4

6:20 pm-1:35 am

2 stops30h 15m

$198

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 5/3

8:02 am-1:46 am

1 stop16h 44m

$308

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 5/3

8:47 pm-2:00 pm

2 stops16h 13m

$339

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/5

Showing 1-10 of 16 results
1
2

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, November is the cheapest month in which you can book a flight from Chicago to Trinidad (average of $435). Flying from Chicago to Trinidad in April is currently the most expensive (average of $628). 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 December 7, 2025.

One of the essential ways to save on airfare from Chicago to Trinidad is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight in the afternoon could potentially save you up to 43% on airfare.

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 December 7, 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
9,072 reviews

Entertainment

7.1

Overall

7.4

Boarding

7.7

Crew

8.1

Food

6.6

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.
United Airlines
7.4
Good
9,072 reviews
United Airlines
7.4
Good
9,072 reviews

Entertainment

7.1

Overall

7.4

Boarding

7.7

Crew

8.1

Food

6.6

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.
American Airlines
7.2
Good
11,046 reviews
United Airlines
7.4
Good
9,072 reviews

Entertainment

7.1

Overall

7.4

Boarding

7.7

Crew

8.1

Food

6.6

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Sunderesh,Dec 2025

AUS - EWR

Smooth flight from Austin to Newark. The crew was friendly.

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.

  • How long is the flight from Chicago to Trinidad?

    There are many flights that can get you from Chicago to Trinidad in 16h 05m. Fly via JetBlue or Air Canada to get the fastest option. Airlines will cover a distance of 2697 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • 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, November is the cheapest month in which you can book a flight from Chicago to Trinidad (average of $435). Flying from Chicago to Trinidad in April is currently the most expensive (average of $628). 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 3 airlines flying from Chicago to Trinidad

Discover the top 3 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 December 7, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$432Average$556FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$528Average$644FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$548Average$628FlexibilityNo cancel feeOn-time69%

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