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$188+ Cheap flights from Trinidad 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 3/2. Fares are subject to change and may not be available on all flights or dates of travel.
POS — CHI
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
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Cheap flight deals from Trinidad to Chicago

Keep the following information in mind while searching for Trinidad to Chicago flight deals. Data was last updated February 20, 2025.

Round-trip from

$434
(Kiwi.com)

One-way from

$188
(Kiwi.com)

Popular in

October

Cheapest in

April
From Trinidad to Chicago (CHI)
Search Deals
One-way flight from Trinidad to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($35 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($38 potential savings vs. average RT price).
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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 February 20, 2025.

This Kiwi.com deal was found by Cheapflights users on 2/19. 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 3/1111:10 amPOS - ORD
1 stop24h 26mMultiple Airlines
Mon 3/178:46 pmORD - POS
2 stops27h 55mMultiple Airlines
Deal found 2/19$434
This Copa Airlines deal was found by Cheapflights users on 2/19. 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.
Wed 3/193:39 amPOS - ORD
1 stop11h 03mCopa Airlines
Tue 3/253:09 pmORD - POS
1 stop9h 32mCopa Airlines
Deal found 2/19$551
This United Airlines deal was found by Cheapflights users on 2/20. 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.
Sat 6/2812:30 amPOS - ORD
1 stop32h 26mUnited Airlines
Mon 8/1110:00 pmORD - POS
1 stop24h 23mUnited Airlines
Deal found 2/20$573
This American Airlines deal was found by Cheapflights users on 2/19. 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.
Tue 5/203:05 pmPOS - ORD
1 stop18h 55mAmerican Airlines
Tue 6/37:16 pmORD - POS
1 stop17h 49mAmerican Airlines
Deal found 2/19$619
This Air Canada deal was found by Cheapflights users on 2/20. 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.
Sun 6/292:25 amPOS - ORD
2 stops32h 29mAir Canada
Mon 8/118:40 amORD - POS
2 stops15h 45mAir Canada
Deal found 2/20$819

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 2,558,603 searches. Data last updated February 20, 2025.

Fly from

Trinidad

Fly to

Chicago

Route

Depart

Return

Price

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 3/11

11:10 am-10:36 am

1 stop24h 26m

Chicago O'Hare Intl

Mon 3/17

8:46 pm-1:41 am

2 stops27h 55m

$434

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 3/19

3:39 am-1:42 pm

1 stop11h 03m

Chicago O'Hare Intl

Tue 3/25

3:09 pm-1:41 am

1 stop9h 32m

$551

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sat 6/28

12:30 am-7:56 am

1 stop32h 26m

Chicago O'Hare Intl

Tue 8/12

9:30 am-11:23 pm

1 stop12h 53m

$573

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 5/20

3:05 pm-9:00 am

1 stop18h 55m

Chicago O'Hare Intl

Tue 6/3

7:16 pm-2:05 pm

1 stop17h 49m

$619

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 6/29

2:25 am-9:54 am

2 stops32h 29m

Chicago O'Hare Intl

Mon 8/11

8:40 am-1:25 am

2 stops15h 45m

$819

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 3/2

7:06 pm-12:37 pm

2 stops43h 31m

$188

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Mon 3/17

3:15 pm-12:20 am

1 stop10h 05m

$359

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 3/7

3:39 am-12:42 pm

1 stop11h 03m

$391

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 2/28

9:59 pm-10:47 am

1 stop14h 48m

$394

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sat 3/15

12:30 am-9:24 pm

1 stop21h 54m

$402

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/20

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, August is the cheapest month in which you can book a flight from Trinidad to Chicago (average of $245). Flying from Trinidad 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 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 February 20, 2025.

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 February 20, 2025.
Copa Airlines
7.6
Good
1,510 reviews

Entertainment

6.9

Overall

7.6

Food

6.9

Crew

8.1

Boarding

7.8

Comfort

7.4

Reviews

1 / 20

4.0
Okay

Anonymous,Jan 2025

PTY - ORD

Our first flight was good. The return flight is a different story. I picked and paid for seat 11D and then checked in with that same seat assignment. When I boarded the plain I somehow had lost that seat and was stuck in a middle seat that I was not happy with for a 5 hour flight. The food was terrible - I could not even eat the chicken and "cheese" sandwich it was so bad. The difference in the two flights was amazing - the one from the Chicago to Panama City was great - seating and food. The return flight was very different.

Copa Airlines
7.6
Good
1,510 reviews
Copa Airlines
7.6
Good
1,510 reviews

Entertainment

6.9

Overall

7.6

Food

6.9

Crew

8.1

Boarding

7.8

Comfort

7.4

Reviews

1 / 20

4.0
Okay

Anonymous,Jan 2025

PTY - ORD

Our first flight was good. The return flight is a different story. I picked and paid for seat 11D and then checked in with that same seat assignment. When I boarded the plain I somehow had lost that seat and was stuck in a middle seat that I was not happy with for a 5 hour flight. The food was terrible - I could not even eat the chicken and "cheese" sandwich it was so bad. The difference in the two flights was amazing - the one from the Chicago to Panama City was great - seating and food. The return flight was very different.

JetBlue
7.4
Good
3,070 reviews
Copa Airlines
7.6
Good
1,510 reviews

Entertainment

6.9

Overall

7.6

Food

6.9

Crew

8.1

Boarding

7.8

Comfort

7.4

Reviews

1 / 20

4.0
Okay

Anonymous,Jan 2025

PTY - ORD

Our first flight was good. The return flight is a different story. I picked and paid for seat 11D and then checked in with that same seat assignment. When I boarded the plain I somehow had lost that seat and was stuck in a middle seat that I was not happy with for a 5 hour flight. The food was terrible - I could not even eat the chicken and "cheese" sandwich it was so bad. The difference in the two flights was amazing - the one from the Chicago to Panama City was great - seating and food. The return flight was very different.

United Airlines
7.4
Good
8,766 reviews
Copa Airlines
7.6
Good
1,510 reviews

Entertainment

6.9

Overall

7.6

Food

6.9

Crew

8.1

Boarding

7.8

Comfort

7.4

Reviews

1 / 20

4.0
Okay

Anonymous,Jan 2025

PTY - ORD

Our first flight was good. The return flight is a different story. I picked and paid for seat 11D and then checked in with that same seat assignment. When I boarded the plain I somehow had lost that seat and was stuck in a middle seat that I was not happy with for a 5 hour flight. The food was terrible - I could not even eat the chicken and "cheese" sandwich it was so bad. The difference in the two flights was amazing - the one from the Chicago to Panama City was great - seating and food. The return flight was very different.

American Airlines
7.2
Good
10,000 reviews
Copa Airlines
7.6
Good
1,510 reviews

Entertainment

6.9

Overall

7.6

Food

6.9

Crew

8.1

Boarding

7.8

Comfort

7.4

Reviews

1 / 20

4.0
Okay

Anonymous,Jan 2025

PTY - ORD

Our first flight was good. The return flight is a different story. I picked and paid for seat 11D and then checked in with that same seat assignment. When I boarded the plain I somehow had lost that seat and was stuck in a middle seat that I was not happy with for a 5 hour flight. The food was terrible - I could not even eat the chicken and "cheese" sandwich it was so bad. The difference in the two flights was amazing - the one from the Chicago to Panama City was great - seating and food. The return flight was very different.

Air Canada
7.0
Good
8,748 reviews
Copa Airlines
7.6
Good
1,510 reviews

Entertainment

6.9

Overall

7.6

Food

6.9

Crew

8.1

Boarding

7.8

Comfort

7.4

Reviews

1 / 20

4.0
Okay

Anonymous,Jan 2025

PTY - ORD

Our first flight was good. The return flight is a different story. I picked and paid for seat 11D and then checked in with that same seat assignment. When I boarded the plain I somehow had lost that seat and was stuck in a middle seat that I was not happy with for a 5 hour flight. The food was terrible - I could not even eat the chicken and "cheese" sandwich it was so bad. The difference in the two flights was amazing - the one from the Chicago to Panama City was great - seating and food. The return flight was very different.

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.

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

    One-way options have recently been found by users for as low as $359 on American Airlines. Other airlines that offer cheap prices include Copa Airlines from $391 and JetBlue from $394 one-way.

  • 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, August is the cheapest month in which you can book a flight from Trinidad to Chicago (average of $245). Flying from Trinidad 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?

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

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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 2,558,603 searches. Data last updated February 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$505Average$627FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$556Average$646FlexibilityNo cancel feeOn-time71%
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