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Trinidad and Tobago

$236+ 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 12/23. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — POS
Nov 30 — Dec 71
Sun 11/30
Sun 12/7
1 adult, Economy
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Find 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 October 31, 2025.

This Air Canada deal was found by Cheapflights users on 10/28. 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.
Sat 11/228:15 pmORD - POS
1 stop26h 55mAir Canada
Fri 11/282:15 amPOS - ORD
1 stop12h 46mAir Canada
Deal found 10/28$433
This Air Canada deal was found by Cheapflights users on 10/30. 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 11/2012:50 pmORD - POS
2 stops34h 20mAir Canada
Sun 11/302:15 amPOS - ORD
2 stops18h 40mAir Canada
Deal found 10/30$443
This Kiwi.com deal was found by Cheapflights users on 10/31. 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.
Mon 12/87:41 pmORD - POS
1 stop21h 14mMultiple Airlines
Fri 12/1210:10 amPOS - ORD
1 stop26h 58mMultiple Airlines
Deal found 10/31$448
This Kiwi.com deal was found by Cheapflights users on 10/31. 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 12/77:10 amORD - POS
1 stop10h 50mMultiple Airlines
Fri 12/1210:10 amPOS - ORD
1 stop26h 58mMultiple Airlines
Deal found 10/31$458
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 11/205:00 amORD - POS
1 stop13h 00mMultiple Airlines
Mon 12/12:38 pmPOS - ORD
2 stops44h 39mMultiple Airlines
Deal found 10/29$479

Cheap 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 October 31, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$433
(Air Canada)

One-way from

$236
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$575
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. 17% potential increase in price ($146 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 11% potential price decrease ($73 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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 October 31, 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

Sat 11/22

3:55 pm-1:10 am

1 stop31h 15m

Port of Spain Piarco Intl

Sun 11/30

2:15 am-6:55 pm

2 stops18h 40m

$443

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 11/20

12:50 pm-1:10 am

2 stops34h 20m

Port of Spain Piarco Intl

Sun 11/30

2:15 am-6:55 pm

2 stops18h 40m

$443

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 3/19

7:15 am-12:10 am

2 stops15h 55m

Port of Spain Piarco Intl

Thu 3/26

1:15 am-2:55 pm

2 stops14h 40m

$483

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 11/22

8:15 pm-1:10 am

1 stop26h 55m

Port of Spain Piarco Intl

Fri 11/28

2:15 am-1:01 pm

1 stop12h 46m

$483

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 3/13

3:22 pm-1:46 am

1 stop9h 24m

Port of Spain Piarco Intl

Wed 3/18

2:16 pm-1:04 am

1 stop11h 48m

$527

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 3/19

3:22 pm-1:46 am

1 stop9h 24m

Port of Spain Piarco Intl

Fri 3/27

2:16 pm-1:04 am

1 stop11h 48m

$527

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 1/14

2:13 pm-1:44 am

1 stop9h 31m

Port of Spain Piarco Intl

Mon 1/19

3:40 am-10:21 pm

1 stop20h 41m

$527

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 3/12

3:22 pm-1:46 am

1 stop9h 24m

Port of Spain Piarco Intl

Wed 3/18

2:16 pm-1:04 am

1 stop11h 48m

$527

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 12/23

6:05 pm-1:31 pm

2 stops17h 26m

$236

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 12/17

7:33 am-1:48 am

1 stop16h 15m

$263

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

Showing 1-10 of 12 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 $436). Flying from Chicago to Trinidad and Tobago in July is currently the most expensive (average of $613). 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 October 31, 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 October 31, 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
8,995 reviews

Boarding

7.7

Crew

8.1

Overall

7.4

Comfort

7.3

Entertainment

7.1

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
United Airlines
7.4
Good
8,995 reviews
United Airlines
7.4
Good
8,995 reviews

Boarding

7.7

Crew

8.1

Overall

7.4

Comfort

7.3

Entertainment

7.1

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000
American Airlines
7.2
Good
11,031 reviews
United Airlines
7.4
Good
8,995 reviews

Boarding

7.7

Crew

8.1

Overall

7.4

Comfort

7.3

Entertainment

7.1

Food

6.6

Reviews

1 / 20
2.0
Mediocre

Sebrena,Oct 2025

IAH - RSW

The worst that I have ever experienced in my life so bad if it was free I'm not ever going to use your Airline again I dont believe ..... very disappointed 😞 😔0000000000000

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 55m. 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 $436). Flying from Chicago to Trinidad and Tobago in July is currently the most expensive (average of $613). 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

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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 October 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$432Average$556FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$487Average$556FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$560Average$628FlexibilityNo cancel feeOn-time69%

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