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Trinidad and Tobago

$251+ Cheap flights from Chicago (CHI) to Trinidad and Tobago

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 12/24. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — POS
jan 16 — jan 231
sex 1/16
sex 1/23
1 adult, Economy
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Cheap flight deals from Chicago to Trinidad and Tobago

Cheapest flights from Chicago to Trinidad and Tobago
Explore the most affordable flight options available from Chicago to Trinidad and Tobago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on dezembro 17, 2025.

This Expedia deal was found by Cheapflights users on 12/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sex 12/197:41 pmORD - POS
2 stops32h 37mJetBlue
qua 1/78:20 amPOS - ORD
2 stops35h 23mJetBlue
Deal found 12/16$759
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
dom 12/215:05 amORD - POS
2 stops22h 10mMultiple Airlines
qui 1/89:10 amPOS - ORD
1 stop11h 06mMultiple Airlines
Deal found 12/16$765
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
dom 12/215:05 amORD - POS
2 stops22h 10mMultiple Airlines
sex 1/99:10 amPOS - ORD
1 stop11h 06mMultiple Airlines
Deal found 12/16$777
This Mytrip deal was found by Cheapflights users on 12/16. 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.
qua 12/174:38 pmORD - POS
2 stops19h 17mMultiple Airlines
ter 12/232:15 amPOS - ORD
1 stop14h 55mMultiple Airlines
Deal found 12/16$804
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
dom 12/215:05 amORD - POS
2 stops22h 10mMultiple Airlines
qua 1/79:10 amPOS - ORD
1 stop25h 08mMultiple Airlines
Deal found 12/16$846
This Kiwi.com deal was found by Cheapflights users on 12/16. 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.
qua 12/175:40 amORD - POS
2 stops12h 40mMultiple Airlines
qui 1/89:10 amPOS - ORD
1 stop11h 06mMultiple Airlines
Deal found 12/16$867
This Expedia deal was found by Cheapflights users on 12/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qui 12/187:41 pmORD - POS
2 stops32h 37mJetBlue
ter 1/68:20 amPOS - ORD
2 stops35h 23mJetBlue
Deal found 12/16$874
This Gotogate deal was found by Cheapflights users on 12/17. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ter 12/238:30 pmORD - TAB
2 stops20h 00mMultiple Airlines
sex 12/2610:20 pmTAB - ORD
2 stops23h 25mMultiple Airlines
Deal found 12/17$1,314

Find flight deals from Chicago to Trinidad and Tobago

Keep the following information in mind while searching for Chicago to Trinidad and Tobago flight deals. Data was last updated dezembro 17, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$391
(Trip.com)

One-way from

$251
(Expedia)

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 and Tobago
Search Deals
One-way flight from Chicago (CHI) to Trinidad and Tobago
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 and Tobago 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 dezembro 17, 2025.
Use the filters below to find and compare flights from Chicago to Trinidad and Tobago that are best for you.

Fly from

Chicago

Fly to

Trinidad and Tobago

Route

Depart

Return

Price

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

qui 1/15

5:15 am-8:00 pm

1 stop12h 45m

Port of Spain Piarco Intl

qui 1/22

10:10 am-9:03 pm

1 stop12h 53m

$391

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

sex 1/30

7:20 am-8:00 pm

1 stop10h 40m

Port of Spain Piarco Intl

sex 2/6

10:10 am-7:38 pm

1 stop11h 28m

$435

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

sáb 2/7

8:40 pm-1:20 am

1 stop26h 40m

Port of Spain Piarco Intl

sex 2/13

2:20 am-3:10 pm

1 stop14h 50m

$443

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

sáb 2/7

8:40 pm-1:20 am

1 stop26h 40m

Port of Spain Piarco Intl

qui 2/12

2:20 am-6:52 pm

2 stops18h 32m

$443

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

qui 3/12

6:04 pm-12:20 am

2 stops29h 16m

Port of Spain Piarco Intl

ter 3/17

1:20 am-6:52 pm

2 stops18h 32m

$473

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

sex 3/13

2:00 pm-12:20 am

1 stop9h 20m

Port of Spain Piarco Intl

ter 3/17

1:20 am-6:52 pm

2 stops18h 32m

$473

ChicagoScarborough

ORD - TAB

ORDTAB

Chicago O'Hare Intl

ter 12/23

8:30 pm-6:30 pm

2 stops20h 00m

Scarborough ANR Robinson Intl

sex 12/26

10:20 pm-7:45 pm

2 stops23h 25m

$1,314

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

ter 12/23

7:41 pm-2:30 pm

2 stops16h 49m

$391

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

qua 12/24

8:30 pm-1:10 am

1 stop26h 40m

$403

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

ter 12/23

5:00 am-8:20 pm

3 stops37h 20m

$420

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

Showing 1-10 of 17 results
1
2

Best time to book a flight from Chicago to Trinidad and Tobago

Have a flexible travel schedule? Discover the best time to fly to Trinidad and Tobago 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 and Tobago

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

Currently, November is the cheapest month in which you can book a flight from Chicago to Trinidad and Tobago (average of $435). Flying from Chicago to Trinidad and Tobago 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 TT?

Find hourly flight availability from Chicago to Trinidad and Tobago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated dezembro 17, 2025.

It’s optimal to fly from Chicago to Trinidad and Tobago in the afternoon. By choosing this option you can save up to 43% on the cost of your flight, compared to a flight in the evening.

Reviews of airlines servicing Trinidad and Tobago

Get insights into the airlines that provide service to Trinidad and Tobago. 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 and Tobago. Reviews last updated dezembro 17, 2025.
Read through reviews of airlines operating flights from Chicago to Trinidad and Tobago, such as United Airlines and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,092 reviews

Crew

8.1

Boarding

7.7

Food

6.6

Overall

7.4

Entertainment

7.1

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
9,092 reviews
United Airlines
7.4
Good
9,092 reviews

Crew

8.1

Boarding

7.7

Food

6.6

Overall

7.4

Entertainment

7.1

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
11,049 reviews
United Airlines
7.4
Good
9,092 reviews

Crew

8.1

Boarding

7.7

Food

6.6

Overall

7.4

Entertainment

7.1

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 and Tobago. 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 and Tobago?

    Departing from Chicago to Trinidad and Tobago will take you 26h 40m. The distance between Chicago and Trinidad and Tobago is about 2697 mi.

  • Can I find deals for flights from Chicago to Trinidad and Tobago that include hotel bookings?

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

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

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

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

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

    Currently, November is the cheapest month in which you can book a flight from Chicago to Trinidad and Tobago (average of $435). Flying from Chicago to Trinidad and Tobago 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Chicago to Trinidad and Tobago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 3 airlines flying from Chicago to Trinidad and Tobago

Discover the top 3 airlines that operate flights from Chicago to Trinidad and Tobago. 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 dezembro 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$432Average$556FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$528Average$634FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$548Average$628FlexibilityNo cancel feeOn-time69%

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