HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Trinidad

$193+ Cheap flights from Chicago (CHI) to Trinidad

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 1/21. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — POS
Nov 15 — Nov 221
Sat 11/15
Sat 11/22
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Trinidad 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.

Cheap flight deals from Chicago to Trinidad

Keep the following information in mind while searching for Chicago to Trinidad flight deals. Data was last updated October 16, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$433
(Air Canada)

One-way from

$193
(Air Canada)

Popular in

December

Cheapest in

January

Average price

$575
Provider with most accurate pricing for Chicago (CHI)-Port of Spain Piarco Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago (CHI)-Port of Spain Piarco Intl flights.
Search Deals
From Chicago (CHI) to Trinidad
Search Deals
One-way flight from Chicago (CHI) to Trinidad
Search Deals
Highest demand for flights based on searches. 17% potential increase in price ($146 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 11% potential price decrease ($73 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

Find flight deals from Chicago to Trinidad

Cheapest flights from Chicago to Trinidad
Explore the most affordable flight options available from Chicago to Trinidad. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 16, 2025.

This Air Canada deal was found by Cheapflights users on 10/15. 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.
Thu 11/207:05 amORD - POS
2 stops16h 05mAir Canada
Fri 11/282:15 amPOS - ORD
1 stop12h 46mAir Canada
Deal found 10/15$433
This Air Canada deal was found by Cheapflights users on 10/15. 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 10/192:00 pmORD - POS
1 stop10h 20mAir Canada
Mon 10/202:25 amPOS - ORD
2 stops17h 29mAir Canada
Deal found 10/15$438
This Air Canada deal was found by Cheapflights users on 10/15. 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.
Fri 11/216:05 pmORD - POS
2 stops53h 05mAir Canada
Fri 11/282:15 amPOS - ORD
1 stop14h 55mAir Canada
Deal found 10/15$443
This Mytrip deal was found by Cheapflights users on 10/14. 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 11/298:15 pmORD - POS
1 stop26h 55mMultiple Airlines
Sat 12/69:10 amPOS - ORD
1 stop11h 26mMultiple Airlines
Deal found 10/14$460
This Kiwi.com deal was found by Cheapflights users on 10/14. 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.
Thu 11/1312:17 pmORD - POS
1 stop14h 58mMultiple Airlines
Mon 11/172:26 pmPOS - ORD
2 stops24h 19mMultiple Airlines
Deal found 10/14$466
This Kiwi.com deal was found by Cheapflights users on 10/15. 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.
Fri 11/1412:17 pmORD - POS
1 stop28h 38mMultiple Airlines
Fri 11/219:10 amPOS - ORD
1 stop27h 25mMultiple Airlines
Deal found 10/15$474
This Air Canada deal was found by Cheapflights users on 10/15. 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.
Fri 11/1410:00 amORD - POS
1 stop13h 10mAir Canada
Thu 11/202:15 amPOS - ORD
1 stop14h 55mAir Canada
Deal found 10/15$483

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Trinidad 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 October 16, 2025.
Use the filters below to find and compare flights from Chicago to Trinidad that are best for you.

Fly from

Chicago

Fly to

Trinidad

Route

Depart

Return

Price

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 3/28

8:15 pm-12:15 am

1 stop27h 00m

Port of Spain Piarco Intl

Fri 4/3

1:15 am-1:00 pm

1 stop12h 45m

$433

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 11/20

7:05 am-1:10 am

2 stops16h 05m

Port of Spain Piarco Intl

Fri 11/28

2:15 am-3:10 pm

1 stop14h 55m

$433

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 11/22

8:15 pm-1:10 am

1 stop26h 55m

Port of Spain Piarco Intl

Fri 11/28

2:15 am-3:10 pm

1 stop14h 55m

$433

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 2/3

7:15 am-1:10 am

2 stops15h 55m

Port of Spain Piarco Intl

Tue 2/10

2:15 am-8:00 pm

2 stops19h 45m

$443

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 11/13

12:17 pm-5:15 am

1 stop14h 58m

Port of Spain Piarco Intl

Mon 11/17

2:26 pm-12:45 pm

2 stops24h 19m

$466

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 2/2

3:55 pm-1:10 am

1 stop31h 15m

Port of Spain Piarco Intl

Thu 2/5

2:15 am-6:55 pm

2 stops18h 40m

$493

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 3/14

8:53 am-11:23 pm

1 stop13h 30m

Port of Spain Piarco Intl

Fri 3/20

12:30 am-10:07 am

1 stop10h 37m

$549

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 1/21

8:15 pm-1:10 am

1 stop26h 55m

$193

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 1/21

8:41 am-6:55 pm

3 stops32h 14m

$290

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 12/17

9:45 am-11:59 pm

1 stop12h 14m

$391

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/14

Best time to book a flight from Chicago to Trinidad

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

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

Currently, October is the cheapest month in which you can book a flight from Chicago to Trinidad (average of $449). Flying from Chicago to Trinidad in July is currently the most expensive (average of $613). 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 LAZ?

Find hourly flight availability from Chicago to Trinidad. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated October 16, 2025.

One of the essential ways to save on airfare from Chicago to Trinidad is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight in the afternoon could potentially save you up to 43% on airfare.

Reviews of airlines servicing Trinidad

Get insights into the airlines that provide service to Trinidad. 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. Reviews last updated October 16, 2025.
Peruse reviews from past customers who have flown with United Airlines and American Airlines from Chicago to Trinidad to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
8,978 reviews

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Crew

8.1

Overall

7.4

Food

6.6

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.
United Airlines
7.4
Good
8,978 reviews
United Airlines
7.4
Good
8,978 reviews

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Crew

8.1

Overall

7.4

Food

6.6

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.
American Airlines
7.2
Good
11,045 reviews
United Airlines
7.4
Good
8,978 reviews

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Crew

8.1

Overall

7.4

Food

6.6

Reviews

1 / 20
4.0
Okay

Tim,Sep 2025

IAD - GSP

This was pretty bad. It’s chaos at the Dulles boarding gates for the small regional jets because they use one gate to board 3-4 flights at a time. So, it’s difficult knowing where and when to go. There is little space for any size of carrry-on, so most had to gate check their bags. However, the worst of it was that our single flight attendant fell asleep before we took off and the pilot couldn’t do so until she responded to his messages. My wife had to wake her up! So we were a little late leaving. Not to be thwarted, the flight attendant fell asleep right after take off and there was no sight of her during the flight. When the aircraft touched down, a tray of unsecured canned drinks came crashing onto the aisle up front. I can only assume someone didn’t do what they were supposed to. The pilot was great, but I’m sure he must not be happy with this crew member.

Related info for your journey

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

  • How long is the flight from Chicago to Trinidad?

    There are many flights that can get you from Chicago to Trinidad in 27h. Fly via Air Canada to get the fastest option. Airlines will cover a distance of 2697 mi.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Chicago to Trinidad 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?

    Currently, October is the cheapest month in which you can book a flight from Chicago to Trinidad (average of $449). Flying from Chicago to Trinidad in July is currently the most expensive (average of $613). 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

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

Top 3 airlines flying from Chicago to Trinidad

Discover the top 3 airlines that operate flights from Chicago to Trinidad. 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 October 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$432Average$556FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$480Average$627FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$487Average$581FlexibilityNo 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.