Chicago

$267+ 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 5/2. Fares are subject to change and may not be available on all flights or dates of travel.
POS — CHI
abr. 8 — abr. 151
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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 abril 3, 2025.

Round-trip from

$485
(Kiwi.com)

One-way from

$267
(Mytrip)
From Trinidad and Tobago to Chicago (CHI)
One-way flight from Trinidad and Tobago to Chicago (CHI)

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 abril 3, 2025.

This Kiwi.com deal was found by Cheapflights users on 4/2. 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.
jue. 6/510:10 amPOS - ORD
1 stop14h 55mMultiple Airlines
sáb. 6/79:55 amORD - POS
1 stop32h 00mMultiple Airlines
Deal found 4/2$485
This Air Canada deal was found by Cheapflights users on 4/1. 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.
lun. 6/22:25 amPOS - ORD
2 stops30h 34mAir Canada
mié. 6/46:15 pmORD - POS
2 stops54h 10mAir Canada
Deal found 4/1$538
This United Airlines deal was found by Cheapflights users on 4/1. 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.
vie. 5/3012:30 amPOS - ORD
1 stop10h 25mUnited Airlines
mié. 6/49:40 pmORD - POS
1 stop24h 43mUnited Airlines
Deal found 4/1$561
This American Airlines deal was found by Cheapflights users on 4/2. 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.
mar. 5/203:05 pmPOS - ORD
1 stop18h 55mAmerican Airlines
mar. 6/35:00 amORD - POS
1 stop8h 05mAmerican Airlines
Deal found 4/2$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 abril 3, 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

jue. 6/5

10:10 am-12:05 am

1 stop14h 55m

Chicago O'Hare Intl

sáb. 6/7

9:55 am-6:55 pm

1 stop32h 00m

$485

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

lun. 6/2

2:25 am-7:59 am

2 stops30h 34m

Chicago O'Hare Intl

mié. 6/4

6:15 pm-1:25 am

2 stops54h 10m

$538

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

vie. 5/30

12:30 am-9:55 am

1 stop10h 25m

Chicago O'Hare Intl

mar. 6/3

8:10 pm-11:23 pm

1 stop26h 13m

$561

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

mar. 5/20

3:05 pm-9:00 am

1 stop18h 55m

Chicago O'Hare Intl

mar. 6/3

5:00 am-2:05 pm

1 stop8h 05m

$563

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

vie. 5/2

10:10 am-9:24 am

1 stop24h 14m

$267

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

jue. 5/1

12:30 am-12:15 am

1 stop24h 45m

$308

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/2

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 abril 3, 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 abril 3, 2025.
Read through reviews of airlines operating flights from Trinidad and Tobago to Chicago, such as United Airlines, American Airlines and Air Canada. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Food

6.6

Comfort

7.3

Crew

8.1

Boarding

7.7

Overall

7.4

Entertainment

7.0

Reviews

1 / 20
4.0
Okay

Patti,Feb 2025

FCO - EWR

The food was inedible! We are in the food business and aren’t sure who got this contract. But prisoners eat better. The food was so bad. I ate just a small amount and it made me nauseous. Everything is over microwaved too. And what is with the options? Vegan and vegetarian, but no keto or carnivore? I get that may be more expensive. But I’d gladly pay if it even was an option. But it’s not. There are many fresh options that could have been offered that don’t have to be heated too!

Food

6.6

Comfort

7.3

Crew

8.1

Boarding

7.7

Overall

7.4

Entertainment

7.0

Reviews

1 / 20
4.0
Okay

Patti,Feb 2025

FCO - EWR

The food was inedible! We are in the food business and aren’t sure who got this contract. But prisoners eat better. The food was so bad. I ate just a small amount and it made me nauseous. Everything is over microwaved too. And what is with the options? Vegan and vegetarian, but no keto or carnivore? I get that may be more expensive. But I’d gladly pay if it even was an option. But it’s not. There are many fresh options that could have been offered that don’t have to be heated too!

Food

6.6

Comfort

7.3

Crew

8.1

Boarding

7.7

Overall

7.4

Entertainment

7.0

Reviews

1 / 20
4.0
Okay

Patti,Feb 2025

FCO - EWR

The food was inedible! We are in the food business and aren’t sure who got this contract. But prisoners eat better. The food was so bad. I ate just a small amount and it made me nauseous. Everything is over microwaved too. And what is with the options? Vegan and vegetarian, but no keto or carnivore? I get that may be more expensive. But I’d gladly pay if it even was an option. But it’s not. There are many fresh options that could have been offered that don’t have to be heated too!

Food

6.6

Comfort

7.3

Crew

8.1

Boarding

7.7

Overall

7.4

Entertainment

7.0

Reviews

1 / 20
4.0
Okay

Patti,Feb 2025

FCO - EWR

The food was inedible! We are in the food business and aren’t sure who got this contract. But prisoners eat better. The food was so bad. I ate just a small amount and it made me nauseous. Everything is over microwaved too. And what is with the options? Vegan and vegetarian, but no keto or carnivore? I get that may be more expensive. But I’d gladly pay if it even was an option. But it’s not. There are many fresh options that could have been offered that don’t have to be heated too!

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.
  • 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
New Buffalo
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 abril 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$493Average$603FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$561Average$663FlexibilityNo cancel feeOn-time71%

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