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Port of Spain

$249+ Cheap flights from O'Hare Intl (ORD) to Port of Spain (POS)

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 8/30. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — POS
May 27 — Jun 31
Wed 5/27
Wed 6/3
1 adult, Economy
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Cheap flight deals from O'Hare Intl to Port of Spain

Cheapest flights from O'Hare Intl to Port of Spain
Explore the most affordable flight options available from O'Hare Intl to Port of Spain. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 27, 2026.

This Trip.com deal was found by Cheapflights users on 4/23. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/254:15 pm
ORD
-
POS
1 stop31h 05m
Air Canada
Thu 4/301:25 am
POS
-
ORD
1 stop19h 15m
Air Canada
Deal found 4/23$499
This Kiwi.com deal was found by Cheapflights users on 4/26. 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 6/187:52 am
ORD
-
POS
1 stop11h 08m
Multiple Airlines
Mon 6/2210:10 am
POS
-
ORD
1 stop30h 17m
Multiple Airlines
Deal found 4/26$507
This Travelocity deal was found by Cheapflights users on 4/22. 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 4/267:55 am
ORD
-
POS
1 stop15h 25m
Air Canada
Sun 5/31:25 am
POS
-
ORD
1 stop14h 30m
Air Canada
Deal found 4/22$517
This Air Canada deal was found by Cheapflights users on 4/25. 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.
Sat 4/259:20 pm
ORD
-
POS
1 stop26h 00m
Air Canada
Fri 5/11:25 am
POS
-
ORD
1 stop13h 00m
Air Canada
Deal found 4/25$522
This Kiwi.com deal was found by Cheapflights users on 4/24. 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 5/285:05 am
ORD
-
POS
1 stop13h 55m
Multiple Airlines
Sun 5/3110:10 am
POS
-
ORD
1 stop27h 27m
Multiple Airlines
Deal found 4/24$533
This Kiwi.com deal was found by Cheapflights users on 4/26. 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 6/101:50 pm
ORD
-
POS
2 stops28h 05m
Multiple Airlines
Wed 6/179:10 am
POS
-
ORD
1 stop27h 53m
Multiple Airlines
Deal found 4/26$542
This FlightHub deal was found by Cheapflights users on 4/26. 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.
Thu 6/186:22 pm
ORD
-
POS
2 stops28h 53m
Air Canada
Sun 6/211:25 am
POS
-
ORD
2 stops18h 22m
Air Canada
Deal found 4/26$556
This Mytrip deal was found by Cheapflights users on 4/24. 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.
Fri 5/12:15 pm
ORD
-
POS
1 stop9h 00m
Multiple Airlines
Fri 5/159:10 am
POS
-
ORD
1 stop15h 46m
Multiple Airlines
Deal found 4/24$557

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

Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) to Port of Spain (POS). 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 April 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$507
(Kiwi.com)

One-way from

$249
(Orbitz)

Popular in

April

Cheapest in

November

Average price

$794
Provider with most accurate pricing for Chicago O'Hare Intl-Port of Spain Piarco Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago O'Hare Intl-Port of Spain Piarco Intl flights.
Search Deals
From Chicago O'Hare Intl to Port of Spain Piarco Intl
Search Deals
One-way flight from Chicago O'Hare Intl to Port of Spain Piarco Intl
Search Deals
Highest demand for flights based on searches. 6% potential increase in price ($43 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from O'Hare Intl to Port of Spain 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 April 27, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Port of Spain that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 5/28

5:05 am-8:00 pm

1 stop13h 55m

Port of Spain Piarco Intl

Sun 5/31

10:10 am-12:37 pm

1 stop27h 27m

$533

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Tue 8/25

8:40 pm-12:15 am

1 stop26h 35m

Port of Spain Piarco Intl

Mon 8/31

1:25 am-1:22 pm

1 stop12h 57m

$576

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 5/25

8:05 am-8:00 pm

1 stop10h 55m

Port of Spain Piarco Intl

Sun 5/31

10:10 am-7:55 am

2 stops22h 45m

$589

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 6/15

1:50 pm-6:55 pm

2 stops52h 05m

Port of Spain Piarco Intl

Wed 6/24

9:10 am-12:03 pm

1 stop27h 53m

$592

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 5/21

8:35 pm-12:15 am

1 stop26h 40m

Port of Spain Piarco Intl

Mon 5/25

1:25 am-1:25 pm

1 stop13h 00m

$610

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 6/10

8:51 am-11:23 pm

1 stop13h 32m

Port of Spain Piarco Intl

Tue 6/16

12:30 am-10:20 am

1 stop10h 50m

$630

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 6/21

1:00 am-1:16 pm

1 stop11h 16m

Port of Spain Piarco Intl

Sun 6/28

3:49 am-2:06 pm

1 stop11h 17m

$633
Quickest round-trip

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 6/18

3:21 pm-1:46 am

1 stop9h 25m

Port of Spain Piarco Intl

Sat 6/20

3:49 am-2:06 pm

1 stop11h 17m

$633
Cheapest one-way
Quickest one-way

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 8/30

2:15 pm-12:15 am

1 stop9h 00m

$249

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 5/2

8:35 pm-12:15 am

1 stop26h 40m

$254

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/25

Showing 1-10 of 12 resultsSorted by cheapest first
1
2

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

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 O'Hare Intl to Port of Spain in April.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy2 starsTrust Score*2 stars
JustAirTicketPrice Accuracy-Trust Score*1 star

*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 Chicago O'Hare Intl Airport-Port of Spain flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago O'Hare Intl Airport-Port of Spain flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago O'Hare Intl Airport-Port of Spain flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago O'Hare Intl Airport-Port of Spain 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 Chicago O'Hare Intl Airport-Port of Spain 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 O'Hare Intl to Port of Spain

Have a flexible travel schedule? Discover the best time to fly to Port of Spain 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 Port of Spain

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

Currently, November is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Port of Spain (average of $443). Flying from Chicago O'Hare Intl Airport to Port of Spain in April is currently the most expensive (average of $794). 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.

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

Reviews of airlines servicing Port of Spain

Get insights into the airlines that provide service to Port of Spain. 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 Port of Spain. Reviews last updated April 27, 2026.
Get a feel of what it's like to fly with Copa Airlines,United Airlines, andAmerican Airlines from Chicago O'Hare Intl Airport to Port of Spain by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Copa Airlines
7.5
Good
1,580 reviews

Comfort

7.4

Overall

7.5

Food

6.8

Boarding

7.8

Entertainment

6.8

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Apr 2026

LIM - PTY

Fast boarding, polite and helpful staff. Lowest cost across all airlines
Copa Airlines
7.5
Good
1,580 reviews
Copa Airlines
7.5
Good
1,580 reviews

Comfort

7.4

Overall

7.5

Food

6.8

Boarding

7.8

Entertainment

6.8

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Apr 2026

LIM - PTY

Fast boarding, polite and helpful staff. Lowest cost across all airlines
United Airlines
7.4
Good
9,669 reviews
Copa Airlines
7.5
Good
1,580 reviews

Comfort

7.4

Overall

7.5

Food

6.8

Boarding

7.8

Entertainment

6.8

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Apr 2026

LIM - PTY

Fast boarding, polite and helpful staff. Lowest cost across all airlines
American Airlines
7.1
Good
11,668 reviews
Copa Airlines
7.5
Good
1,580 reviews

Comfort

7.4

Overall

7.5

Food

6.8

Boarding

7.8

Entertainment

6.8

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Apr 2026

LIM - PTY

Fast boarding, polite and helpful staff. Lowest cost across all airlines
Air Canada
7.1
Good
10,974 reviews
Copa Airlines
7.5
Good
1,580 reviews

Comfort

7.4

Overall

7.5

Food

6.8

Boarding

7.8

Entertainment

6.8

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Apr 2026

LIM - PTY

Fast boarding, polite and helpful staff. Lowest cost across all airlines

Related info for your journey

Find useful and relevant information for your journey from O'Hare Intl to Port of Spain. 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 into for flights to Port of Spain from Chicago O'Hare Intl?

    Port of Spain Piarco Intl (POS) is the airport you will fly into if you book a flight from Chicago O'Hare Intl to Port of Spain. You should not have trouble finding flights to Piarco Intl from Chicago O'Hare Intl; the airport handles an average of 0 inbound flights from Chicago O'Hare Intl per day. You should also have plenty of airline options to choose from since 4 airlines have flights to the Port of Spain airport from Chicago O'Hare Intl. It is only a 12.6 mi journey from Piarco Intl (POS) to Port of Spain’s city center.

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

    Departing from Chicago O'Hare Intl Airport to Port of Spain will take you 26h 35m. The distance from Chicago O'Hare Intl Airport to Port of Spain is about 2697 mi.

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

    Flying on Air Canada is currently your cheapest option to Port of Spain, with prices starting at $392. Additional round-trip tickets that might be worth considering are offered by Copa Airlines and American Airlines, with the lowest prices starting at $472 and $548, respectively. You may be able to fly from Chicago O'Hare Intl Airport to Port of Spain for 37% less than the average price by searching for these airlines.

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

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

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

    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 Port of Spain.

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

    Yes. Cheapflights offers flight deals from O'Hare Intl to Port of Spain 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 Port of Spain?

    Currently, November is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Port of Spain (average of $443). Flying from Chicago O'Hare Intl Airport to Port of Spain in April is currently the most expensive (average of $794). 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

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Complete your trip

Complete your trip to Port of Spain by adding a car rental and/or hotel reservation to your travel itinerary.
Port of Spain car rentals
Port of Spain Piarco Intl Airport car rentals
Scarborough ANR Robinson Intl Airport car rentals

Top 4 airlines flying from O'Hare Intl to Port of Spain

Discover the top 4 airlines that operate flights from O'Hare Intl to Port of Spain. 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 April 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$392Average$516FlexibilityNo cancel feeOn-time67%
Copa AirlinesCheapest$472Average$597FlexibilityNo cancel feeOn-time70%
American AirlinesCheapest$548Average$688FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$548Average$629FlexibilityNo cancel feeOn-time69%

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