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Trinidad and Tobago

$188+ 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 1/14. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — POS
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
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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 September 16, 2025.

Round-trip from

$423
(Air Canada)

One-way from

$188
(Air Canada)

Popular in

December

Cheapest in

January

Average price

$618
From Chicago (CHI) to Trinidad and Tobago
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One-way flight from Chicago (CHI) to Trinidad and Tobago
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Highest demand for flights based on searches. 6% potential increase in price ($50 potential increase over avg. RT price).
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Cheapest flight prices on average. 9% potential price decrease ($66 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 September 16, 2025.

This Air Canada deal was found by Cheapflights users on 9/14. 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.
Mon 9/152:00 pmORD - POS
1 stop10h 20mAir Canada
Fri 9/262:25 amPOS - ORD
1 stop11h 49mAir Canada
Deal found 9/14$423
This Air Canada deal was found by Cheapflights users on 9/13. 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.
Fri 11/212:00 pmORD - POS
1 stop9h 10mAir Canada
Fri 11/282:15 amPOS - ORD
2 stops18h 40mAir Canada
Deal found 9/13$428
This Air Canada deal was found by Cheapflights users on 9/13. 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.
Fri 11/212:00 pmORD - POS
1 stop9h 10mAir Canada
Thu 11/272:15 amPOS - ORD
1 stop14h 55mAir Canada
Deal found 9/13$473
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/227:43 pmORD - POS
2 stops29h 03mMultiple Airlines
Sun 10/266:25 pmPOS - ORD
1 stop15h 57mMultiple Airlines
Deal found 9/15$492
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 12/41:35 pmORD - POS
2 stops21h 42mMultiple Airlines
Thu 12/119:10 amPOS - ORD
1 stop29h 20mMultiple Airlines
Deal found 9/15$519
This Copa Airlines deal was found by Cheapflights users on 9/14. 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.
Mon 10/63:07 pmORD - POS
1 stop9h 39mCopa Airlines
Wed 10/82:40 pmPOS - ORD
1 stop10h 41mCopa Airlines
Deal found 9/14$532
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Tue 10/147:43 pmORD - POS
2 stops29h 03mMultiple Airlines
Tue 10/218:55 amPOS - ORD
1 stop28h 50mMultiple Airlines
Deal found 9/16$536
This United Airlines deal was found by Cheapflights users on 9/14. 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.
Thu 9/187:00 amORD - POS
1 stop15h 23mUnited Airlines
Wed 10/1512:30 amPOS - ORD
1 stop10h 40mUnited Airlines
Deal found 9/14$548
This Mytrip deal was found by Cheapflights users on 9/15. 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.
Thu 12/48:41 amORD - TAB
2 stops20h 09mMultiple Airlines
Thu 12/116:55 amTAB - ORD
3 stops18h 10mMultiple Airlines
Deal found 9/15$788

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 September 16, 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

Fri 11/21

2:00 pm-1:10 am

1 stop9h 10m

Port of Spain Piarco Intl

Fri 11/28

2:15 am-3:10 pm

1 stop14h 55m

$423

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 2/2

8:15 pm-1:10 am

1 stop26h 55m

Port of Spain Piarco Intl

Sun 2/8

2:15 am-3:10 pm

1 stop14h 55m

$423

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-3:10 pm

1 stop14h 55m

$423

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 3/6

7:15 am-1:10 am

2 stops15h 55m

Port of Spain Piarco Intl

Thu 3/12

1:15 am-8:05 am

2 stops31h 50m

$433

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 10/22

7:43 pm-1:46 am

2 stops29h 03m

Port of Spain Piarco Intl

Sun 10/26

6:25 pm-9:22 am

1 stop15h 57m

$493

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 11/21

7:15 am-1:10 am

2 stops15h 55m

Port of Spain Piarco Intl

Thu 11/27

2:15 am-1:01 pm

1 stop12h 46m

$523

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 10/6

3:07 pm-1:46 am

1 stop9h 39m

Port of Spain Piarco Intl

Wed 10/8

2:40 pm-12:21 am

1 stop10h 41m

$532

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 1/5

10:35 am-12:23 am

1 stop11h 48m

Port of Spain Piarco Intl

Mon 1/12

1:30 am-7:50 pm

1 stop20h 20m

$548

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 12/4

7:35 am-12:23 am

1 stop14h 48m

Port of Spain Piarco Intl

Wed 12/10

1:30 am-2:41 pm

1 stop15h 11m

$548

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 10/22

7:10 am-11:23 pm

1 stop15h 13m

Port of Spain Piarco Intl

Sat 10/25

12:30 am-10:53 am

1 stop11h 23m

$548

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/14

Showing 1-10 of 20 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, October 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 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 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 September 16, 2025.

When flying from Chicago to Trinidad and Tobago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 September 16, 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
8,924 reviews

Comfort

7.3

Food

6.6

Crew

8.1

Boarding

7.7

Overall

7.4

Entertainment

7.1

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
8,924 reviews
United Airlines
7.4
Good
8,924 reviews

Comfort

7.3

Food

6.6

Crew

8.1

Boarding

7.7

Overall

7.4

Entertainment

7.1

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
8,924 reviews

Comfort

7.3

Food

6.6

Crew

8.1

Boarding

7.7

Overall

7.4

Entertainment

7.1

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 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 9h 10m. 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, October 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 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

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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$480Average$622FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$487Average$566FlexibilityNo cancel feeOn-time71%
Air CanadaCheapest$516Average$556FlexibilityNo cancel feeOn-time67%

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