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O'Hare Intl

$210+ Cheap flights from Port of Spain (POS) to O'Hare Intl (ORD)

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 4/2. Fares are subject to change and may not be available on all flights or dates of travel.
POS — ORD
Mar 18 — Mar 251
Wed 3/18
Wed 3/25
1 adult, Economy
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Cheap flight deals from Port of Spain to O'Hare Intl

Cheapest flights from Port of Spain to O'Hare Intl
Explore the most affordable flight options available from Port of Spain to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 16, 2026.

This Priceline deal was found by Cheapflights users on 2/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/311:20 am
POS
-
ORD
2 stops18h 33m
Air Canada
Wed 4/89:15 pm
ORD
-
POS
1 stop26h 05m
Air Canada
Deal found 2/15$359
This Booking.com deal was found by Cheapflights users on 2/15. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/81:20 am
POS
-
ORD
2 stops34h 58m
Air Canada
Tue 4/72:00 pm
ORD
-
POS
1 stop9h 20m
Air Canada
Deal found 2/15$362
This Mytrip deal was found by Cheapflights users on 2/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/21:20 am
POS
-
ORD
1 stop14h 55m
Air Canada
Thu 5/288:20 pm
ORD
-
POS
1 stop26h 55m
Air Canada
Deal found 2/12$401
This Air Canada deal was found by Cheapflights users on 2/14. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/241:20 am
POS
-
ORD
2 stops42h 32m
Air Canada
Sat 4/119:15 pm
ORD
-
POS
1 stop26h 05m
Air Canada
Deal found 2/14$420
This Mytrip deal was found by Cheapflights users on 2/15. 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 3/311:20 am
POS
-
ORD
1 stop12h 45m
Multiple Airlines
Wed 4/87:31 pm
ORD
-
POS
3 stops27h 49m
Multiple Airlines
Deal found 2/15$434
This Mytrip deal was found by Cheapflights users on 2/13. 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.
Sun 3/291:20 am
POS
-
ORD
2 stops34h 33m
Air Canada
Sat 4/186:40 pm
ORD
-
POS
1 stop28h 40m
Air Canada
Deal found 2/13$477
This Air Canada deal was found by Cheapflights users on 2/13. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/291:20 am
POS
-
ORD
1 stop12h 45m
Air Canada
Fri 4/178:40 am
ORD
-
POS
2 stops14h 40m
Air Canada
Deal found 2/13$527
This Mytrip deal was found by Cheapflights users on 2/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/21:20 am
POS
-
ORD
1 stop14h 55m
Multiple Airlines
Thu 5/286:34 pm
ORD
-
POS
3 stops28h 41m
Multiple Airlines
Deal found 2/12$542

Find flight deals from Port of Spain to O'Hare Intl

Discover tips and strategies to find the most affordable flight options for your journey from Port of Spain (POS) to O'Hare Intl (ORD). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated February 16, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$359
(Priceline)

One-way from

$210
(Mytrip)

Popular in

April

Cheapest in

December

Average price

$506
Provider with most accurate pricing for Port of Spain Piarco Intl-Chicago O'Hare Intl flight deals.
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Provider most trusted by Cheapflights users for Port of Spain Piarco Intl-Chicago O'Hare Intl flights.
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From Port of Spain Piarco Intl to Chicago O'Hare Intl
Search Deals
One-way flight from Port of Spain Piarco Intl to Chicago O'Hare Intl
Search Deals
Highest demand for flights based on searches. 40% potential increase in price ($445 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 14% potential price decrease ($83 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 Port of Spain to O'Hare Intl 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 16, 2026.
Use the filters below to find and compare flights from Port of Spain to Chicago O'Hare Intl Airport that are best for you.

Fly from

Port of Spain

Fly to

O'Hare Intl

Route

Depart

Return

Price

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 3/31

1:20 am-6:53 pm

2 stops18h 33m

Chicago O'Hare Intl

Wed 4/8

9:15 pm-12:20 am

1 stop26h 05m

$359

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 3/8

1:20 am-7:45 pm

1 stop19h 25m

Chicago O'Hare Intl

Tue 4/7

7:55 am-12:20 am

1 stop15h 25m

$359

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 3/24

1:20 am-6:52 pm

2 stops42h 32m

Chicago O'Hare Intl

Sat 4/11

9:15 pm-12:20 am

1 stop26h 05m

$420

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 3/31

1:20 am-1:05 pm

1 stop12h 45m

Chicago O'Hare Intl

Wed 4/8

7:31 pm-12:20 am

3 stops27h 49m

$434

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 3/29

1:20 am-10:53 am

2 stops34h 33m

Chicago O'Hare Intl

Sat 4/18

6:40 pm-12:20 am

1 stop28h 40m

$477

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 3/29

1:20 am-1:05 pm

1 stop12h 45m

Chicago O'Hare Intl

Fri 4/17

8:40 am-12:20 am

2 stops14h 40m

$527

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 4/2

1:20 am-3:15 pm

1 stop14h 55m

Chicago O'Hare Intl

Thu 5/28

6:34 pm-12:15 am

3 stops28h 41m

$542

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 3/29

1:20 am-8:01 am

3 stops31h 41m

Chicago O'Hare Intl

Sat 4/18

6:40 pm-12:20 am

1 stop28h 40m

$553

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sun 3/29

1:20 am-8:01 am

3 stops31h 41m

Chicago O'Hare Intl

Fri 4/17

7:55 am-12:20 am

1 stop15h 25m

$553

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 4/2

1:20 am-3:15 pm

1 stop14h 55m

$210

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/12

Showing 1-10 of 16 results
1
2

Compare providers for flights from Port of Spain to O'Hare Intl

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Port of Spain to O'Hare Intl in February.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*2 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Port of Spain-Chicago O'Hare Intl Airport flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Port of Spain-Chicago O'Hare Intl Airport flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Port of Spain-Chicago O'Hare Intl Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Port of Spain-Chicago O'Hare Intl Airport flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Port of Spain-Chicago O'Hare Intl Airport flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Port of Spain to O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from Port of Spain 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.

Reviews of airlines servicing O'Hare Intl

Get insights into the airlines that provide service to O'Hare Intl. 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 O'Hare Intl. Reviews last updated February 16, 2026.
See what other customers who have flown with Copa Airlines, United Airlines, and American Airlines from Port of Spain to Chicago O'Hare Intl Airport have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Copa Airlines
7.5
Good
1,555 reviews

Overall

7.5

Boarding

7.8

Entertainment

6.8

Crew

8.1

Food

6.8

Comfort

7.4

Reviews

1 / 20
2.0
Mediocre

Juan,Dec 2025

EZE - PTY

The outbound flight from Boston was awful. The handicapped services were the worst i have ever seen. NEVER AGAIN. THIS WAS NOT WORTH ANYWHERE NEAR $4K.
Copa Airlines
7.5
Good
1,555 reviews
Copa Airlines
7.5
Good
1,555 reviews

Overall

7.5

Boarding

7.8

Entertainment

6.8

Crew

8.1

Food

6.8

Comfort

7.4

Reviews

1 / 20
2.0
Mediocre

Juan,Dec 2025

EZE - PTY

The outbound flight from Boston was awful. The handicapped services were the worst i have ever seen. NEVER AGAIN. THIS WAS NOT WORTH ANYWHERE NEAR $4K.
United Airlines
7.4
Good
9,299 reviews
Copa Airlines
7.5
Good
1,555 reviews

Overall

7.5

Boarding

7.8

Entertainment

6.8

Crew

8.1

Food

6.8

Comfort

7.4

Reviews

1 / 20
2.0
Mediocre

Juan,Dec 2025

EZE - PTY

The outbound flight from Boston was awful. The handicapped services were the worst i have ever seen. NEVER AGAIN. THIS WAS NOT WORTH ANYWHERE NEAR $4K.
American Airlines
7.2
Good
11,291 reviews
Copa Airlines
7.5
Good
1,555 reviews

Overall

7.5

Boarding

7.8

Entertainment

6.8

Crew

8.1

Food

6.8

Comfort

7.4

Reviews

1 / 20
2.0
Mediocre

Juan,Dec 2025

EZE - PTY

The outbound flight from Boston was awful. The handicapped services were the worst i have ever seen. NEVER AGAIN. THIS WAS NOT WORTH ANYWHERE NEAR $4K.

Related info for your journey

Find useful and relevant information for your journey from Port of Spain to O'Hare Intl. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Port of Spain to Chicago O'Hare Intl?

    Port of Spain Piarco Intl (POS), located 12.6 mi from the city center, is the airport you fly out of when you book flights from Port of Spain to Chicago O'Hare Intl. 3 airlines have flights from Piarco Intl to Chicago O'Hare Intl on a regular basis. Booking flights from Port of Spain Piarco Intl to Chicago O'Hare Intl should not be difficult; the airport handles an average of 0 outbound flights to Chicago O'Hare Intl per day.

  • How long is the flight from Port of Spain to Chicago O'Hare Intl Airport?

    There are many flights that can get you from Port of Spain to Chicago O'Hare Intl Airport in 18h 33m. Fly via Air Canada to get the fastest option. The distance from Port of Spain to Chicago O'Hare Intl Airport is about 2697 mi.

  • What are the cheapest airlines flying from Port of Spain to Chicago O'Hare Intl Airport round-trip?

    Cheapflights users have booked flights from Port of Spain to Chicago O'Hare Intl Airport round-trip from $290. Other airlines that can offer you cheap pricing are Copa Airlines, from $299, and American Airlines, from $562. United Airlines is 56% cheaper than the average price of flights available within the next 90 days to this destination.

  • Can I find deals for flights from Port of Spain to O'Hare Intl that include hotel bookings?

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

  • How can I find direct flights from Port of Spain to O'Hare Intl?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Port of Spain to O'Hare Intl.

  • Can I find deals for business class flights from Port of Spain to O'Hare Intl?

    Yes. Cheapflights offers flight deals from Port of Spain to O'Hare Intl by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Chicago O'Hare Intl Airport?

Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locations
Schaumburg
Rosemont
Naperville
Gurnee
Elgin
Hoffman Estates
Beloit
Delavan
Oak Brook
Des Plaines
Downers Grove
Elk Grove Village
Skokie
Libertyville
Lake Geneva
Waukegan
Bridgeview
Kenosha
Warrenville
Aurora

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Top 3 airlines flying from Port of Spain to O'Hare Intl

Discover the top 3 airlines that operate flights from Port of Spain to O'Hare Intl. 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 16, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$290Average$706FlexibilityNo cancel feeOn-time69%
Copa AirlinesCheapest$299Average$374FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$562Average$698FlexibilityNo cancel feeOn-time71%

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