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O'Hare Intl

$248+ 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 12/12. Fares are subject to change and may not be available on all flights or dates of travel.
POS — ORD
Dec 5 — Dec 121
Fri 12/5
Fri 12/12
1 adult, Economy
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Find 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 November 5, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/4. 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.
Sat 12/69:10 amPOS - ORD
1 stop11h 26mMultiple Airlines
Sat 12/135:40 amORD - POS
2 stops12h 40mMultiple Airlines
Deal found 11/4$561
This United Airlines deal was found by Cheapflights users on 11/4. 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.
Fri 12/51:30 amPOS - ORD
1 stop23h 26mUnited Airlines
Sat 12/138:49 amORD - POS
1 stop13h 34mUnited Airlines
Deal found 11/4$572
This United Airlines deal was found by Cheapflights users on 11/5. 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 11/221:30 amPOS - ORD
1 stop11h 26mUnited Airlines
Sun 11/308:50 amORD - POS
1 stop13h 33mUnited Airlines
Deal found 11/5$667
This Mytrip deal was found by Cheapflights users on 11/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/189:10 amPOS - ORD
1 stop9h 50mMultiple Airlines
Thu 12/257:57 pmORD - POS
2 stops22h 03mMultiple Airlines
Deal found 11/3$669
This United Airlines deal was found by Cheapflights users on 11/4. 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.
Thu 12/182:20 amPOS - ORD
1 stop11h 45mUnited Airlines
Fri 12/268:54 amORD - POS
1 stop13h 29mUnited Airlines
Deal found 11/4$721

Cheap 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 November 5, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$463
(Priceline)

One-way from

$248
(Trip.com)

Popular in

April

Cheapest in

June

Average price

$586
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
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One-way flight from Port of Spain Piarco Intl to Chicago O'Hare Intl
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Highest demand for flights based on searches. 23% potential increase in price ($206 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 11% potential price decrease ($72 potential savings vs. average RT price).
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Average for round-trip flights in November 2025
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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 November 5, 2025.
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

Fri 2/13

2:20 am-6:52 pm

2 stops18h 32m

Chicago O'Hare Intl

Tue 2/17

7:15 am-1:20 am

2 stops16h 05m

$463

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 1/13

2:20 am-6:51 pm

2 stops18h 31m

Chicago O'Hare Intl

Tue 1/20

7:15 am-1:20 am

2 stops16h 05m

$463

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 2/26

2:20 am-6:52 pm

2 stops42h 32m

Chicago O'Hare Intl

Tue 3/3

2:00 pm-1:20 am

1 stop9h 20m

$483

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sat 12/6

9:10 am-6:36 pm

1 stop11h 26m

Chicago O'Hare Intl

Sat 12/13

5:40 am-8:20 pm

2 stops12h 40m

$561

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 1/14

2:16 pm-12:24 am

1 stop12h 08m

Chicago O'Hare Intl

Tue 1/20

7:35 am-1:44 am

1 stop16h 09m

$562

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Sat 2/14

4:47 pm-12:36 am

1 stop9h 49m

Chicago O'Hare Intl

Tue 2/17

9:08 pm-3:30 pm

2 stops16h 22m

$579

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 2/27

2:16 pm-12:04 am

1 stop11h 48m

Chicago O'Hare Intl

Tue 3/3

7:34 am-1:15 pm

1 stop27h 41m

$610

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 12/12

9:10 am-6:36 pm

1 stop11h 26m

$248

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 12/12

5:42 pm-9:52 pm

1 stop30h 10m

$290

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 12/11

1:30 am-10:56 pm

1 stop23h 26m

$313

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/3

Showing 1-10 of 13 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 November.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*3 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Port of Spain-Chicago O'Hare Intl Airport flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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.

Cheapflights Insights

Everything you need to know about your flight from Port of Spain to Chicago O'Hare Intl Airport

What is the cheapest month to book a flight from Port of Spain to Chicago O'Hare Intl Airport?

Currently, December is the cheapest month in which you can book a flight from Port of Spain to Chicago O'Hare Intl Airport (average of $304). Flying from Port of Spain to Chicago O'Hare Intl Airport in April is currently the most expensive (average of $632). 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 POS to ORD?

Find hourly flight availability from Port of Spain to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 5, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 19% on flights from Port of Spain to Chicago O'Hare Intl Airport by exploring options for tickets at noon.

How much does it cost to fly round-trip from Port of Spain to Chicago O'Hare Intl Airport?

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 November 5, 2025.
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
7.6
Good
1,561 reviews

Comfort

7.4

Crew

8.1

Food

6.9

Entertainment

6.8

Overall

7.6

Boarding

7.8

Reviews

1 / 20
4.0
Okay

Juan Pablo,Sep 2025

PTY - VVI

not a good expirience, the plane was packed, the seats wear very unconftrable, coudent conect with the entratainmente service on the plane, the onboarding was in charge of a very angry lady i really had a unplesent trip
Copa Airlines
7.6
Good
1,561 reviews
Copa Airlines
7.6
Good
1,561 reviews

Comfort

7.4

Crew

8.1

Food

6.9

Entertainment

6.8

Overall

7.6

Boarding

7.8

Reviews

1 / 20
4.0
Okay

Juan Pablo,Sep 2025

PTY - VVI

not a good expirience, the plane was packed, the seats wear very unconftrable, coudent conect with the entratainmente service on the plane, the onboarding was in charge of a very angry lady i really had a unplesent trip
United Airlines
7.4
Good
9,001 reviews
Copa Airlines
7.6
Good
1,561 reviews

Comfort

7.4

Crew

8.1

Food

6.9

Entertainment

6.8

Overall

7.6

Boarding

7.8

Reviews

1 / 20
4.0
Okay

Juan Pablo,Sep 2025

PTY - VVI

not a good expirience, the plane was packed, the seats wear very unconftrable, coudent conect with the entratainmente service on the plane, the onboarding was in charge of a very angry lady i really had a unplesent trip
American Airlines
7.2
Good
11,039 reviews
Copa Airlines
7.6
Good
1,561 reviews

Comfort

7.4

Crew

8.1

Food

6.9

Entertainment

6.8

Overall

7.6

Boarding

7.8

Reviews

1 / 20
4.0
Okay

Juan Pablo,Sep 2025

PTY - VVI

not a good expirience, the plane was packed, the seats wear very unconftrable, coudent conect with the entratainmente service on the plane, the onboarding was in charge of a very angry lady i really had a unplesent trip

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 32m. 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 $299. Other airlines that can offer you cheap pricing are United Airlines, from $559, and American Airlines, from $562. Copa 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.

  • What is the cheapest month to book a flight from Port of Spain to Chicago O'Hare Intl Airport?

    Currently, December is the cheapest month in which you can book a flight from Port of Spain to Chicago O'Hare Intl Airport (average of $304). Flying from Port of Spain to Chicago O'Hare Intl Airport in April is currently the most expensive (average of $632). 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 Chicago O'Hare Intl Airport?

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

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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 November 5, 2025.
AirlineCheapestAverageFlexibilityOn-time
Copa AirlinesCheapest$299Average$542FlexibilityNo cancel feeOn-time70%
United AirlinesCheapest$559Average$579FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$562Average$676FlexibilityNo cancel feeOn-time71%

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