HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Trinidad and Tobago

$189+ Cheap flights from O'Hare Intl (ORD) 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 3/15. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — POS
Mar 5 — Mar 121
Thu 3/5
Thu 3/12
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from O'Hare Intl 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 O'Hare Intl to Trinidad and Tobago

Cheapest flights from O'Hare Intl to Trinidad and Tobago
Explore the most affordable flight options available from O'Hare Intl to Trinidad and Tobago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 3, 2026.

This Air Canada deal was found by Cheapflights users on 2/3. 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.
Mon 3/308:20 pm
ORD
-
POS
1 stop27h 00m
Air Canada
Sun 4/51:20 am
POS
-
ORD
1 stop12h 45m
Air Canada
Deal found 2/3$358
This Air Canada deal was found by Cheapflights users on 2/3. 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 2/278:00 am
ORD
-
POS
1 stop15h 20m
Air Canada
Thu 3/52:20 am
POS
-
ORD
1 stop17h 28m
Air Canada
Deal found 2/3$368
This Travelocity deal was found by Cheapflights users on 2/1. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/297:13 am
ORD
-
POS
2 stops16h 07m
Air Canada
Fri 4/31:20 am
POS
-
ORD
2 stops31h 40m
Air Canada
Deal found 2/1$375
This Air Canada deal was found by Cheapflights users on 2/2. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/1510:00 am
ORD
-
POS
1 stop13h 20m
Air Canada
Tue 3/171:20 am
POS
-
ORD
2 stops18h 32m
Air Canada
Deal found 2/2$398
This Orbitz deal was found by Cheapflights users on 2/1. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/410:00 am
ORD
-
POS
2 stops19h 17m
JetBlue
Sun 3/88:45 am
POS
-
ORD
2 stops25h 25m
JetBlue
Deal found 2/1$402
This Air Canada deal was found by Cheapflights users on 2/3. 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.
Mon 3/168:40 pm
ORD
-
POS
1 stop26h 40m
Air Canada
Thu 3/191:20 am
POS
-
ORD
1 stop12h 41m
Air Canada
Deal found 2/3$418
This Kiwi.com deal was found by Cheapflights users on 2/2. 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.
Wed 3/184:51 pm
ORD
-
POS
1 stop25h 04m
Multiple Airlines
Mon 3/239:10 am
POS
-
ORD
1 stop24h 15m
Multiple Airlines
Deal found 2/2$424
This Air Canada deal was found by Cheapflights users on 2/2. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/157:15 am
ORD
-
POS
2 stops16h 05m
Air Canada
Thu 3/191:20 am
POS
-
ORD
2 stops14h 35m
Air Canada
Deal found 2/2$425
This Mytrip deal was found by Cheapflights users on 2/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/125:05 am
ORD
-
TAB
2 stops24h 05m
Multiple Airlines
Tue 3/1710:20 pm
TAB
-
ORD
2 stops21h 11m
Multiple Airlines
Deal found 2/2$578

Find flight deals from O'Hare Intl to Trinidad and Tobago

Keep the following information in mind while searching for O'Hare Intl to Trinidad and Tobago flight deals. Data was last updated February 3, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$358
(Air Canada)

One-way from

$189
(Air Canada)

Popular in

December

Cheapest in

October

Average price

$902
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 O'Hare Intl to Trinidad and Tobago
Search Deals
One-way flight from Chicago O'Hare Intl to Trinidad and Tobago
Search Deals
Highest demand for flights based on searches. 36% potential increase in price ($449 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 17% potential price decrease ($117 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from O'Hare Intl 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 February 3, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Trinidad and Tobago that are best for you.

Fly from

O'Hare Intl

Fly to

Trinidad and Tobago

Route

Depart

Return

Price

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 3/28

8:40 pm-12:20 am

1 stop26h 40m

Port of Spain Piarco Intl

Fri 4/3

1:20 am-1:05 pm

1 stop12h 45m

$358

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 3/30

8:20 pm-12:20 am

1 stop27h 00m

Port of Spain Piarco Intl

Sun 4/5

1:20 am-1:05 pm

1 stop12h 45m

$358

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 3/29

8:40 am-12:20 am

2 stops14h 40m

Port of Spain Piarco Intl

Fri 4/3

1:20 am-1:05 pm

1 stop12h 45m

$361

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 2/27

8:00 am-1:20 am

1 stop15h 20m

Port of Spain Piarco Intl

Thu 3/5

2:20 am-5:48 pm

1 stop17h 28m

$368

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 3/15

10:00 am-12:20 am

1 stop13h 20m

Port of Spain Piarco Intl

Tue 3/17

1:20 am-6:52 pm

2 stops18h 32m

$398

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 3/16

8:40 pm-12:20 am

1 stop26h 40m

Port of Spain Piarco Intl

Thu 3/19

1:20 am-2:55 pm

2 stops14h 35m

$421

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 3/18

4:51 pm-6:55 pm

1 stop25h 04m

Port of Spain Piarco Intl

Mon 3/23

9:10 am-8:25 am

1 stop24h 15m

$424

ChicagoScarborough

ORD - TAB

ORDTAB

Chicago O'Hare Intl

Thu 3/12

5:05 am-6:10 am

2 stops24h 05m

Scarborough ANR Robinson Intl

Tue 3/17

10:20 pm-6:31 pm

2 stops21h 11m

$578

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 3/15

7:15 am-12:20 am

2 stops16h 05m

$189

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 3/15

4:51 pm-1:46 am

3 stops55h 55m

$272

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/2

Showing 1-10 of 12 results
1
2

Best time to book a flight from O'Hare Intl to Trinidad and Tobago

Have a flexible travel schedule? Discover the best time to fly to Trinidad and Tobago from O'Hare Intl 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 O'Hare Intl Airport to Trinidad and Tobago

What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Trinidad and Tobago?

Currently, November is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Trinidad and Tobago (average of $435). Flying from Chicago O'Hare Intl Airport to Trinidad and Tobago in April is currently the most expensive (average of $628). 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 February 3, 2026.
See what other customers who have flown with United Airlines, American Airlines, and Air Canada from Chicago O'Hare Intl Airport to Trinidad and Tobago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,236 reviews

Overall

7.4

Boarding

7.7

Entertainment

7.1

Crew

8.1

Food

6.6

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
United Airlines
7.4
Good
9,236 reviews
United Airlines
7.4
Good
9,236 reviews

Overall

7.4

Boarding

7.7

Entertainment

7.1

Crew

8.1

Food

6.6

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
American Airlines
7.2
Good
11,218 reviews
United Airlines
7.4
Good
9,236 reviews

Overall

7.4

Boarding

7.7

Entertainment

7.1

Crew

8.1

Food

6.6

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
Air Canada
7.1
Good
10,684 reviews
United Airlines
7.4
Good
9,236 reviews

Overall

7.4

Boarding

7.7

Entertainment

7.1

Crew

8.1

Food

6.6

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 O'Hare Intl 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 O'Hare Intl Airport to Trinidad and Tobago?

    Air Canada can get you from Chicago O'Hare Intl Airport to Trinidad and Tobago in just under 26h 40m. Your travel time can differ by up to . The distance between Chicago O'Hare Intl Airport and Trinidad and Tobago is about 2697 mi.

  • Can I find deals for flights from O'Hare Intl to Trinidad and Tobago that include hotel bookings?

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

  • How can I find direct flights from O'Hare Intl 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 O'Hare Intl to Trinidad and Tobago.

  • Can I find deals for business class flights from O'Hare Intl to Trinidad and Tobago?

    Yes. Cheapflights offers flight deals from O'Hare Intl 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 O'Hare Intl Airport to Trinidad and Tobago?

    Currently, November is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Trinidad and Tobago (average of $435). Flying from Chicago O'Hare Intl Airport to Trinidad and Tobago in April is currently the most expensive (average of $628). 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 O'Hare Intl to Trinidad and Tobago

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Luis Munoz Marin Intl flights
O'Hare Intl to Punta Cana flights
Midway to Luis Munoz Marin Intl flights
O'Hare Intl to Oranjestad flights
O'Hare Intl to Saint Thomas Island flights
O'Hare Intl to Nassau flights
O'Hare Intl to Montego Bay flights
Midway to Punta Cana flights
O'Hare Intl to Providenciales flights
O'Hare Intl to George Town flights
O'Hare Intl to Simpson Bay flights
Midway to Oranjestad flights
Midway to Nassau flights
O'Hare Intl to Willemstad flights
O'Hare Intl to Santo Domingo flights
Midway to Montego Bay flights
Midway to Saint Thomas Island flights
O'Hare Intl to Castries flights
O'Hare Intl to Christiansted flights
O'Hare Intl to Bridgetown flights
O'Hare Intl to Aguadilla flights
Midway to Santo Domingo flights
O'Hare Intl to St. John's flights
Midway to Providenciales flights
O'Hare Intl to Ponce flights
Midway to Simpson Bay flights
O'Hare Intl to Road Town flights
O'Hare Intl to Santiago de los Caballeros flights
Midway to George Town flights
O'Hare Intl to Puerto Plata flights
O'Hare Intl to Georgetown flights
O'Hare Intl to Port of Spain flights
O'Hare Intl to Kingston flights
Midway to Castries flights
O'Hare Intl to St. George's flights
O'Hare Intl to Kralendijk flights
O'Hare Intl to Castries flights
O'Hare Intl to The Valley flights
O'Hare Intl to Basseterre flights
O'Hare Intl to Marsh Harbour flights
O'Hare Intl to Freeport flights
Midway to Kingston flights
O'Hare Intl to Gustavia flights
O'Hare Intl to Gregory Town flights
O'Hare Intl to Havana flights
Midway to Georgetown flights
Midway to St. John's flights
O'Hare Intl to Fort-de-France flights
O'Hare Intl to Kingstown flights

Top 3 airlines flying from O'Hare Intl to Trinidad and Tobago

Discover the top 3 airlines that operate flights from O'Hare Intl 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 February 3, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$432Average$556FlexibilityNo cancel feeOn-time67%
United AirlinesCheapest$501Average$628FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$528Average$669FlexibilityNo 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.
Site
©2026 Cheapflights