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Trinidad and Tobago

$455+ Cheap flights from Chicago (CHI) to Trinidad and Tobago

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — POS
ago. 5 — ago. 121
mar. 8/5
mar. 8/12
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 julio 31, 2025.

Round-trip from

$455
(Kiwi.com)

Popular in

February

Cheapest in

January

Average price

$735
From Chicago (CHI) to Trinidad and Tobago
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($163 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 9% potential price decrease ($62 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals

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 julio 31, 2025.

This Kiwi.com deal was found by Cheapflights users on 7/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/1610:27 amORD - POS
1 stop31h 28mMultiple Airlines
vie. 9/269:10 amPOS - ORD
1 stop25h 08mMultiple Airlines
Deal found 7/30$455
This Copa Airlines deal was found by Cheapflights users on 7/30. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/193:07 pmORD - POS
1 stop9h 39mCopa Airlines
dom. 9/283:51 amPOS - ORD
1 stop10h 50mCopa Airlines
Deal found 7/30$526
This Air Canada deal was found by Cheapflights users on 7/30. 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.
mar. 11/1110:00 amORD - POS
1 stop13h 15mAir Canada
vie. 11/212:15 amPOS - ORD
1 stop12h 46mAir Canada
Deal found 7/30$537
This American Airlines deal was found by Cheapflights users on 7/31. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/85:00 amORD - POS
1 stop8h 25mAmerican Airlines
mar. 8/197:00 amPOS - ORD
1 stop16h 41mAmerican Airlines
Deal found 7/31$548
This Mytrip deal was found by Cheapflights users on 7/31. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 9/1410:27 amORD - TAB
2 stops24h 13mMultiple Airlines
dom. 9/219:15 amTAB - ORD
2 stops25h 03mMultiple Airlines
Deal found 7/31$548
This United Airlines deal was found by Cheapflights users on 7/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/2212:45 pmORD - POS
1 stop9h 38mUnited Airlines
sáb. 10/2512:30 amPOS - ORD
1 stop20h 26mUnited Airlines
Deal found 7/31$658

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 julio 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

mar. 9/16

10:27 am-6:55 pm

1 stop31h 28m

Port of Spain Piarco Intl

vie. 9/26

9:10 am-9:18 am

1 stop25h 08m

$455

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

vie. 9/19

3:07 pm-1:46 am

1 stop9h 39m

Port of Spain Piarco Intl

dom. 9/28

3:51 am-1:41 pm

1 stop10h 50m

$526

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

mar. 11/11

10:00 am-1:15 am

1 stop13h 15m

Port of Spain Piarco Intl

vie. 11/21

2:15 am-1:01 pm

1 stop12h 46m

$537

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

vie. 9/19

7:15 pm-2:16 pm

1 stop18h 01m

Port of Spain Piarco Intl

lun. 9/29

3:25 pm-11:49 pm

1 stop9h 24m

$548

ChicagoScarborough

ORD - TAB

ORDTAB

Chicago O'Hare Intl

dom. 9/14

10:27 am-11:40 am

2 stops24h 13m

Scarborough ANR Robinson Intl

dom. 9/21

9:15 am-9:18 am

2 stops25h 03m

$548

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

mié. 10/22

12:45 pm-11:23 pm

1 stop9h 38m

Port of Spain Piarco Intl

sáb. 10/25

12:30 am-7:56 pm

1 stop20h 26m

$658

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

mar. 11/25

8:35 pm-4:28 pm

2 stops17h 53m

Port of Spain Piarco Intl

dom. 11/30

5:53 pm-10:45 pm

1 stop30h 52m

$866

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

mié. 12/17

11:57 am-10:15 pm

1 stop8h 18m

$553

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

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 julio 31, 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 julio 31, 2025.
Read through reviews of airlines operating flights from Chicago to Trinidad and Tobago, such as Copa Airlines, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Copa Airlines
7.5
Good
1,493 reviews

Comfort

7.4

Overall

7.5

Boarding

7.8

Food

6.8

Crew

8.1

Entertainment

6.8

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
1,493 reviews
Copa Airlines
7.5
Good
1,493 reviews

Comfort

7.4

Overall

7.5

Boarding

7.8

Food

6.8

Crew

8.1

Entertainment

6.8

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
8,900 reviews
Copa Airlines
7.5
Good
1,493 reviews

Comfort

7.4

Overall

7.5

Boarding

7.8

Food

6.8

Crew

8.1

Entertainment

6.8

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
1,493 reviews

Comfort

7.4

Overall

7.5

Boarding

7.8

Food

6.8

Crew

8.1

Entertainment

6.8

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
9,851 reviews
Copa Airlines
7.5
Good
1,493 reviews

Comfort

7.4

Overall

7.5

Boarding

7.8

Food

6.8

Crew

8.1

Entertainment

6.8

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 and Tobago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • 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 2 airlines flying from Chicago to Trinidad and Tobago

Discover the top 2 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 julio 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$480Average$628FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$487Average$605FlexibilityNo cancel feeOn-time71%

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