HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$341+ Cheap flights from Trinidad to Chicago (CHI)

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 2/2. Fares are subject to change and may not be available on all flights or dates of travel.
POS — CHI
Nov 12 — Nov 191
Tue 11/12
Tue 11/19
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Trinidad to Chicago with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Find flight deals from Trinidad to Chicago

Cheapest flights from Trinidad to Chicago
Explore the most affordable flight options available from Trinidad to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 7, 2024.

This United Airlines deal was found by Cheapflights users on 11/7. 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.
Tue 12/242:20 amPOS - ORD
1 stop11h 18mUnited Airlines
Tue 12/316:00 amORD - POS
1 stop16h 23mUnited Airlines
Deal found 11/7$561
This Mytrip deal was found by Cheapflights users on 11/6. 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.
Sat 12/217:40 amPOS - ORD
3 stops14h 33mMultiple Airlines
Sat 12/288:55 pmORD - POS
2 stops19h 30mMultiple Airlines
Deal found 11/6$660
This American Airlines deal was found by Cheapflights users on 11/7. 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 12/257:05 amPOS - ORD
1 stop29h 16mAmerican Airlines
Tue 12/316:55 pmORD - POS
1 stop18h 47mAmerican Airlines
Deal found 11/7$724

Find flights from Trinidad to Chicago within your budget

Customize your flight search to find flights from Trinidad 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 2,537,365 searches. Data last updated November 7, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 2/2

5:50 pm-10:16 pm

2 stops30h 26m

Chicago O'Hare Intl

Fri 2/7

8:12 pm-4:29 pm

2 stops42h 17m

$341

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 12/6

3:38 am-7:07 pm

2 stops17h 29m

Chicago O'Hare Intl

Sat 12/14

1:00 pm-4:32 pm

1 stop25h 32m

$530

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 12/24

2:20 am-11:38 am

1 stop11h 18m

Chicago O'Hare Intl

Tue 12/31

6:00 am-12:23 am

1 stop16h 23m

$561

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 2/2

4:35 pm-8:59 am

1 stop18h 24m

Chicago O'Hare Intl

Fri 2/7

8:12 am-11:14 pm

2 stops13h 02m

$566

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sat 12/7

4:20 pm-10:33 am

2 stops20h 13m

Chicago O'Hare Intl

Sat 12/14

2:50 pm-3:04 pm

2 stops22h 14m

$686

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 4/17

4:01 am-12:21 am

1 stop21h 20m

Chicago O'Hare Intl

Tue 4/22

7:56 am-1:16 pm

1 stop28h 20m

$740

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 4/16

12:30 am-9:25 am

1 stop9h 55m

Chicago O'Hare Intl

Tue 4/22

9:30 pm-7:50 pm

3 stops21h 20m

$865

Flights are sorted by cheapest first

Deals found on 11/6

Best time to book a flight from Trinidad to Chicago

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

Travel insights for flights from Trinidad to Chicago

Get recent, data-driven insights about flights from Trinidad to Chicago including ideal travel times, pricing trends, and more.

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

Currently, September is the cheapest month in which you can book a flight from Trinidad to Chicago (average of $232). Flying from Trinidad to Chicago in June is currently the most expensive (average of $308). 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 LAZ to CHI?

Find hourly flight availability from Trinidad 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 November 7, 2024.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Trinidad 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 November 7, 2024.
Caribbean Airlines
8.1
Very good
162 reviews

Entertainment

6.6

Overall

8.1

Comfort

7.8

Boarding

8.1

Crew

8.4

Food

6.7

Reviews

1 / 8

The flight attendants on my flight needs training on how to speak to people.

Caribbean Airlines
8.1
Very good
162 reviews
Caribbean Airlines
8.1
Very good
162 reviews

Entertainment

6.6

Overall

8.1

Comfort

7.8

Boarding

8.1

Crew

8.4

Food

6.7

Reviews

1 / 8

The flight attendants on my flight needs training on how to speak to people.

Copa Airlines
7.8
Good
1,850 reviews
Caribbean Airlines
8.1
Very good
162 reviews

Entertainment

6.6

Overall

8.1

Comfort

7.8

Boarding

8.1

Crew

8.4

Food

6.7

Reviews

1 / 8

The flight attendants on my flight needs training on how to speak to people.

United Airlines
7.4
Good
9,206 reviews
Caribbean Airlines
8.1
Very good
162 reviews

Entertainment

6.6

Overall

8.1

Comfort

7.8

Boarding

8.1

Crew

8.4

Food

6.7

Reviews

1 / 8

The flight attendants on my flight needs training on how to speak to people.

American Airlines
7.2
Good
10,000 reviews
Caribbean Airlines
8.1
Very good
162 reviews

Entertainment

6.6

Overall

8.1

Comfort

7.8

Boarding

8.1

Crew

8.4

Food

6.7

Reviews

1 / 8

The flight attendants on my flight needs training on how to speak to people.

British Airways
6.7
Okay
6,840 reviews
Caribbean Airlines
8.1
Very good
162 reviews

Entertainment

6.6

Overall

8.1

Comfort

7.8

Boarding

8.1

Crew

8.4

Food

6.7

Reviews

1 / 8

The flight attendants on my flight needs training on how to speak to people.

Related info for your journey

Find useful and relevant information for your journey from Trinidad 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 to Chicago that include hotel bookings?

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

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

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

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

    Yes. Cheapflights offers flight deals from Trinidad 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 to Chicago?

    Currently, September is the cheapest month in which you can book a flight from Trinidad to Chicago (average of $232). Flying from Trinidad to Chicago in June is currently the most expensive (average of $308). 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 Trinidad to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
Port of Spain to O'Hare Intl flights
Port of Spain to St. Louis flights

Top 2 airlines flying from Trinidad to Chicago

Discover the top 2 airlines that operate flights from Trinidad 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 2,537,365 searches. Data last updated November 7, 2024.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$505Average$671FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$556Average$634FlexibilityNo cancel feeOn-time71%
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.
View all available airlines