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$304+ Cheap flights from Trinidad and Tobago to Chicago (CHI)

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.
POS — CHI
Apr 30 — May 71
Wed 4/30
Wed 5/7
1 adult, Economy
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Cheap flight deals from Trinidad and Tobago to Chicago

Keep the following information in mind while searching for Trinidad and Tobago to Chicago flight deals. Data was last updated April 25, 2025.

Round-trip from

$478
(Kiwi.com)

One-way from

$304
(Justfly.com)
From Trinidad and Tobago to Chicago (CHI)
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One-way flight from Trinidad and Tobago to Chicago (CHI)
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Find flight deals from Trinidad and Tobago to Chicago

Cheapest flights from Trinidad and Tobago to Chicago
Explore the most affordable flight options available from Trinidad and Tobago to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 25, 2025.

This Kiwi.com deal was found by Cheapflights users on 4/24. 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 5/1210:10 amPOS - ORD
1 stop23h 40mMultiple Airlines
Wed 5/149:55 amORD - POS
1 stop32h 00mMultiple Airlines
Deal found 4/24$478
This Priceline deal was found by Cheapflights users on 4/24. 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.
Fri 9/52:25 amPOS - ORD
1 stop13h 39mAir Canada
Sun 9/142:00 pmORD - POS
1 stop10h 25mAir Canada
Deal found 4/24$544
This Copa Airlines deal was found by Cheapflights users on 4/25. 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.
Tue 7/13:48 amPOS - ORD
1 stop10h 54mCopa Airlines
Wed 8/133:07 pmORD - POS
1 stop9h 41mCopa Airlines
Deal found 4/25$551
This United Airlines deal was found by Cheapflights users on 4/24. 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.
Mon 5/1912:30 amPOS - ORD
1 stop10h 41mUnited Airlines
Tue 6/37:10 amORD - POS
1 stop15h 13mUnited Airlines
Deal found 4/24$559
This American Airlines deal was found by Cheapflights users on 4/25. 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.
Wed 7/27:09 amPOS - ORD
1 stop15h 01mAmerican Airlines
Wed 8/139:55 amORD - POS
1 stop10h 35mAmerican Airlines
Deal found 4/25$563

Cheapflights Fare Finder

Customize your flight search to find flights from Trinidad and Tobago to Chicago 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 April 25, 2025.
Use the filters below to find and compare flights from Trinidad and Tobago to Chicago that are best for you.

Fly from

Trinidad and Tobago

Fly to

Chicago

Route

Depart

Return

Price

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Mon 5/12

10:10 am-8:50 am

1 stop23h 40m

Chicago O'Hare Intl

Wed 5/14

9:55 am-6:55 pm

1 stop32h 00m

$478

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 9/5

2:25 am-6:41 pm

2 stops17h 16m

Chicago O'Hare Intl

Sun 9/14

10:40 am-1:25 am

2 stops13h 45m

$544

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 7/1

3:48 am-1:42 pm

1 stop10h 54m

Chicago O'Hare Intl

Wed 8/13

7:54 am-1:48 am

1 stop16h 54m

$551

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Mon 5/19

12:30 am-10:11 am

1 stop10h 41m

Chicago O'Hare Intl

Tue 6/3

7:10 am-11:23 pm

1 stop15h 13m

$559

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 7/2

7:09 am-9:10 pm

1 stop15h 01m

Chicago O'Hare Intl

Wed 8/13

9:55 am-9:30 pm

1 stop10h 35m

$563

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 5/4

2:25 am-6:54 pm

2 stops41h 29m

$304

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 5/4

9:10 am-6:29 pm

2 stops34h 19m

$355

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 5/2

12:30 am-5:10 pm

1 stop17h 40m

$445

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sat 5/3

3:10 pm-8:49 am

2 stops18h 39m

$455

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/25

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

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

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

Currently, August is the cheapest month in which you can book a flight from Trinidad and Tobago to Chicago (average of $245). Flying from Trinidad and Tobago to Chicago in March is currently the most expensive (average of $321). 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 TT to CHI?

Find hourly flight availability from Trinidad and Tobago to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 25, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Trinidad and Tobago to Chicago as you normally would.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated April 25, 2025.
Copa Airlines
7.6
Good
1,411 reviews

Crew

8.1

Boarding

7.8

Entertainment

6.8

Comfort

7.4

Overall

7.6

Food

6.8

Reviews

1 / 20
4.0
Okay

Anonymous,Mar 2025

PTY - JFK

There was no chance for me to choose a seat even if I were willing to pay extra for it when I was doing the check-in on line. My seats were the last row on the plane and they didn't have enough food to give me. I had to eat what was left after everybody else had their choice of food. This is unacceptable. Everyone should have a choice. I paid money just like everybody else. Never had this happened on any other airlines even if my seats were last row on the plane.
Copa Airlines
7.6
Good
1,411 reviews
Copa Airlines
7.6
Good
1,411 reviews

Crew

8.1

Boarding

7.8

Entertainment

6.8

Comfort

7.4

Overall

7.6

Food

6.8

Reviews

1 / 20
4.0
Okay

Anonymous,Mar 2025

PTY - JFK

There was no chance for me to choose a seat even if I were willing to pay extra for it when I was doing the check-in on line. My seats were the last row on the plane and they didn't have enough food to give me. I had to eat what was left after everybody else had their choice of food. This is unacceptable. Everyone should have a choice. I paid money just like everybody else. Never had this happened on any other airlines even if my seats were last row on the plane.
United Airlines
7.4
Good
8,685 reviews
Copa Airlines
7.6
Good
1,411 reviews

Crew

8.1

Boarding

7.8

Entertainment

6.8

Comfort

7.4

Overall

7.6

Food

6.8

Reviews

1 / 20
4.0
Okay

Anonymous,Mar 2025

PTY - JFK

There was no chance for me to choose a seat even if I were willing to pay extra for it when I was doing the check-in on line. My seats were the last row on the plane and they didn't have enough food to give me. I had to eat what was left after everybody else had their choice of food. This is unacceptable. Everyone should have a choice. I paid money just like everybody else. Never had this happened on any other airlines even if my seats were last row on the plane.
American Airlines
7.2
Good
10,000 reviews
Copa Airlines
7.6
Good
1,411 reviews

Crew

8.1

Boarding

7.8

Entertainment

6.8

Comfort

7.4

Overall

7.6

Food

6.8

Reviews

1 / 20
4.0
Okay

Anonymous,Mar 2025

PTY - JFK

There was no chance for me to choose a seat even if I were willing to pay extra for it when I was doing the check-in on line. My seats were the last row on the plane and they didn't have enough food to give me. I had to eat what was left after everybody else had their choice of food. This is unacceptable. Everyone should have a choice. I paid money just like everybody else. Never had this happened on any other airlines even if my seats were last row on the plane.
Air Canada
7.0
Good
9,210 reviews
Copa Airlines
7.6
Good
1,411 reviews

Crew

8.1

Boarding

7.8

Entertainment

6.8

Comfort

7.4

Overall

7.6

Food

6.8

Reviews

1 / 20
4.0
Okay

Anonymous,Mar 2025

PTY - JFK

There was no chance for me to choose a seat even if I were willing to pay extra for it when I was doing the check-in on line. My seats were the last row on the plane and they didn't have enough food to give me. I had to eat what was left after everybody else had their choice of food. This is unacceptable. Everyone should have a choice. I paid money just like everybody else. Never had this happened on any other airlines even if my seats were last row on the plane.

Related info for your journey

Find useful and relevant information for your journey from Trinidad and Tobago to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines to fly from Trinidad and Tobago to Chicago one-way?

    The cheapest airline one-way is Air Canada, with whom users have recently found tickets for as low as $304. However, be on the lookout for offers from United Airlines and American Airlines, as they are both options that can get you from Trinidad and Tobago to Chicago for a low price.

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

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

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

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

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

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

    Currently, August is the cheapest month in which you can book a flight from Trinidad and Tobago to Chicago (average of $245). Flying from Trinidad and Tobago to Chicago in March is currently the most expensive (average of $321). 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

Traveling to a place near Trinidad and Tobago?

Book flights to Trinidad and Tobago if you plan to visit one of these locations
Merrillville
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
Chesterton

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Top 2 airlines flying from Trinidad and Tobago to Chicago

Discover the top 2 airlines that operate flights from Trinidad and Tobago to Chicago. 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 April 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$493Average$613FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$561Average$663FlexibilityNo cancel feeOn-time71%

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