Trinidad and Tobago

$174+ Cheap flights from Chicago (CHI) to Trinidad and Tobago

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 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — POS
Apr 17 — Apr 241
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Chicago to Trinidad and Tobago 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 and Tobago

Cheapest flights from Chicago to Trinidad and Tobago
Explore the most affordable flight options available from Chicago to Trinidad and Tobago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 18, 2026.

This Copa Airlines deal was found by Cheapflights users on 3/15. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/163:22 pm
ORD
-
POS
1 stop9h 24m
Copa Airlines
Wed 3/182:16 pm
POS
-
ORD
1 stop11h 48m
Copa Airlines
Deal found 3/15$384
This Expedia deal was found by Cheapflights users on 3/12. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/99:50 am
ORD
-
POS
1 stop13h 30m
Air Canada
Sun 4/121:20 am
POS
-
ORD
1 stop17h 30m
Air Canada
Deal found 3/12$388
This Expedia deal was found by Cheapflights users on 3/16. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/154:15 pm
ORD
-
POS
1 stop31h 05m
Air Canada
Tue 4/211:20 am
POS
-
ORD
2 stops19h 45m
Air Canada
Deal found 3/16$391
This Air Canada deal was found by Cheapflights users on 3/15. 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.
Tue 4/72:00 pm
ORD
-
POS
1 stop9h 20m
Air Canada
Sun 4/121:20 am
POS
-
ORD
2 stops18h 38m
Air Canada
Deal found 3/15$393
This FlightHub deal was found by Cheapflights users on 3/15. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/86:21 pm
ORD
-
POS
2 stops28h 59m
Air Canada
Sun 4/121:20 am
POS
-
ORD
2 stops31h 38m
Air Canada
Deal found 3/15$398
This Expedia deal was found by Cheapflights users on 3/15. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/46:40 pm
ORD
-
POS
1 stop28h 40m
Air Canada
Sun 4/121:20 am
POS
-
ORD
1 stop17h 30m
Air Canada
Deal found 3/15$413
This FlightHub deal was found by Cheapflights users on 3/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/66:01 pm
ORD
-
POS
2 stops29h 19m
Air Canada
Thu 4/91:20 am
POS
-
ORD
1 stop31h 43m
Air Canada
Deal found 3/14$426
This Gotogate deal was found by Cheapflights users on 3/17. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/176:04 pm
ORD
-
POS
2 stops53h 16m
Air Canada
Sun 3/221:20 am
POS
-
ORD
1 stop19h 25m
Air Canada
Deal found 3/17$478
This Mytrip deal was found by Cheapflights users on 3/15. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/72:00 pm
ORD
-
POS
1 stop9h 20m
Multiple Airlines
Sun 4/121:20 am
POS
-
ORD
3 stops24h 02m
Multiple Airlines
Deal found 3/15$486
This FlightHub deal was found by Cheapflights users on 3/14. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:00 am
ORD
-
POS
2 stops33h 13m
JetBlue
Sun 5/35:38 pm
POS
-
ORD
2 stops28h 58m
JetBlue
Deal found 3/14$489
This Mytrip deal was found by Cheapflights users on 3/13. 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.
Tue 4/286:40 pm
ORD
-
TAB
2 stops22h 50m
Multiple Airlines
Tue 5/511:45 am
TAB
-
ORD
2 stops22h 20m
Multiple Airlines
Deal found 3/13$1,134
This Flightnetwork deal was found by Cheapflights users on 3/17. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/54:37 pm
ORD
-
TAB
2 stops15h 33m
Multiple Airlines
Tue 6/99:55 am
TAB
-
ORD
2 stops24h 10m
Multiple Airlines
Deal found 3/17$1,637

Find flight deals from Chicago to Trinidad and Tobago

Keep the following information in mind while searching for Chicago to Trinidad and Tobago flight deals. Data was last updated March 18, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$384
(Copa Airlines)

One-way from

$174
(Booking.com)

Popular in

December

Cheapest in

February

Average price

$596
Provider with most accurate pricing for Chicago (CHI)-Port of Spain Piarco Intl flight deals.
Provider most trusted by Cheapflights users for Chicago (CHI)-Port of Spain Piarco Intl flights.
From Chicago (CHI) to Trinidad and Tobago
One-way flight from Chicago (CHI) to Trinidad and Tobago
Highest demand for flights based on searches. 35% potential increase in price ($385 potential increase over avg. RT price).
Cheapest flight prices on average. 15% potential price decrease ($92 potential savings vs. average RT price).
Average for round-trip flights in March 2026

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Trinidad and Tobago 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 March 18, 2026.
Use the filters below to find and compare flights from Chicago to Trinidad and Tobago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 4/28

3:05 pm-1:40 am

1 stop9h 35m

Port of Spain Piarco Intl

Mon 5/4

3:49 am-2:06 pm

1 stop11h 17m

$508

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 5/10

3:21 pm-1:46 am

1 stop9h 25m

Port of Spain Piarco Intl

Wed 5/20

2:22 pm-1:15 am

1 stop11h 53m

$508

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 4/9

8:40 am-12:20 am

2 stops14h 40m

Port of Spain Piarco Intl

Sun 4/12

1:20 am-6:58 pm

2 stops18h 38m

$546

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 5/1

6:00 am-4:13 pm

2 stops33h 13m

Port of Spain Piarco Intl

Sun 5/3

5:38 pm-7:41 am

1 stop15h 03m

$552

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 5/29

2:15 pm-12:15 am

1 stop9h 00m

Port of Spain Piarco Intl

Sun 5/31

1:25 am-1:25 pm

1 stop13h 00m

$574

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 4/9

6:01 pm-12:20 am

3 stops29h 19m

Port of Spain Piarco Intl

Sun 4/12

1:20 am-12:22 am

2 stops24h 02m

$576

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 6/11

8:20 pm-12:15 am

1 stop26h 55m

Port of Spain Piarco Intl

Wed 6/17

1:25 am-1:22 pm

1 stop12h 57m

$584

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 3/30

6:21 pm-12:20 am

2 stops28h 59m

Port of Spain Piarco Intl

Sun 4/5

1:20 am-10:53 am

2 stops34h 33m

$601

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 5/14

8:20 pm-12:15 am

1 stop26h 55m

Port of Spain Piarco Intl

Wed 5/20

1:25 am-1:25 pm

1 stop13h 00m

$604

ChicagoScarborough

ORD - TAB

ORDTAB

Chicago O'Hare Intl

Tue 4/28

6:40 pm-6:30 pm

2 stops22h 50m

Scarborough ANR Robinson Intl

Tue 5/5

11:45 am-9:05 am

2 stops22h 20m

$1,134

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/16

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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

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

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

Currently, June is the cheapest month in which you can book a flight from Chicago to Trinidad and Tobago (average of $376). Flying from Chicago to Trinidad and Tobago in January is currently the most expensive (average of $638). 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.

Reviews of airlines servicing Trinidad and Tobago

Get insights into the airlines that provide service to Trinidad and Tobago. 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 and Tobago. Reviews last updated March 18, 2026.
Read through reviews of airlines operating flights from Chicago to Trinidad and Tobago, such as United Airlines,American Airlines, andAir Canada. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Entertainment

7.1

Food

6.6

Boarding

7.7

Overall

7.4

Crew

8.1

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

Entertainment

7.1

Food

6.6

Boarding

7.7

Overall

7.4

Crew

8.1

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

Entertainment

7.1

Food

6.6

Boarding

7.7

Overall

7.4

Crew

8.1

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

Entertainment

7.1

Food

6.6

Boarding

7.7

Overall

7.4

Crew

8.1

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

Related info for your journey

Find useful and relevant information for your journey from Chicago to Trinidad and Tobago. 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 and Tobago?

    Departing from Chicago to Trinidad and Tobago will take you 9h 35m. The distance between Chicago and Trinidad and Tobago is about 2697 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

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

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

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

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

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

    Currently, June is the cheapest month in which you can book a flight from Chicago to Trinidad and Tobago (average of $376). Flying from Chicago to Trinidad and Tobago in January is currently the most expensive (average of $638). 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.

Top 4 airlines flying from Chicago to Trinidad and Tobago

Discover the top 4 airlines that operate flights from Chicago to Trinidad and Tobago. 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 March 18, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$392Average$516FlexibilityNo cancel feeOn-time67%
Copa AirlinesCheapest$472Average$567FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$548Average$688FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$548Average$628FlexibilityNo cancel feeOn-time69%

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.