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Port of Spain

$185+ 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 4/3. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — POS
Mar 25 — Apr 11
Wed 3/25
Wed 4/1
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 February 23, 2026.

This Travelocity deal was found by Cheapflights users on 2/23. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/16:22 pm
ORD
-
POS
2 stops52h 53m
Air Canada
Fri 6/51:25 am
POS
-
ORD
2 stops18h 22m
Air Canada
Deal found 2/23$308
This Orbitz deal was found by Cheapflights users on 2/22. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/229:55 am
ORD
-
POS
1 stop13h 20m
Air Canada
Sun 5/241:25 am
POS
-
ORD
2 stops18h 22m
Air Canada
Deal found 2/22$358
This Priceline deal was found by Cheapflights users on 2/19. 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.
Mon 3/308:20 pm
ORD
-
POS
1 stop27h 00m
Air Canada
Sun 4/51:20 am
POS
-
ORD
2 stops18h 33m
Air Canada
Deal found 2/19$363
This Priceline deal was found by Cheapflights users on 2/23. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/248:40 am
ORD
-
POS
2 stops14h 40m
Air Canada
Sun 4/261:20 am
POS
-
ORD
2 stops18h 33m
Air Canada
Deal found 2/23$366
This Air Canada deal was found by Cheapflights users on 2/19. 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 2/216:04 pm
ORD
-
POS
2 stops29h 16m
Air Canada
Fri 2/272:20 am
POS
-
ORD
1 stop18h 20m
Air Canada
Deal found 2/19$378
This Mytrip deal was found by Cheapflights users on 2/22. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/306:01 pm
ORD
-
POS
3 stops29h 19m
Multiple Airlines
Sun 4/51:20 am
POS
-
ORD
1 stop17h 30m
Multiple Airlines
Deal found 2/22$401
This Expedia deal was found by Cheapflights users on 2/20. 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 3/146:25 pm
ORD
-
POS
1 stop28h 55m
Air Canada
Tue 3/171:20 am
POS
-
ORD
1 stop21h 44m
Air Canada
Deal found 2/20$408

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 February 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$358
(Orbitz)

One-way from

$185
(Air Canada)

Popular in

January

Cheapest in

November

Average price

$669
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. 21% potential increase in price ($187 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($42 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 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 February 23, 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

O'Hare Intl

Fly to

Port of Spain

Route

Depart

Return

Price

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

$363

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 3/28

9:15 pm-12:20 am

1 stop26h 05m

Port of Spain Piarco Intl

Fri 4/3

1:20 am-9:50 am

1 stop9h 30m

$363

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 4/17

8:40 am-12:20 am

2 stops14h 40m

Port of Spain Piarco Intl

Sun 4/19

1:20 am-2:55 pm

2 stops14h 35m

$425

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 3/15

6:04 pm-12:20 am

2 stops53h 16m

Port of Spain Piarco Intl

Thu 3/19

1:20 am-8:00 am

2 stops31h 40m

$438

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 6/1

8:45 am-12:15 am

2 stops14h 30m

Port of Spain Piarco Intl

Fri 6/5

1:25 am-6:47 pm

2 stops18h 22m

$466

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 5/3

3:52 pm-6:55 pm

1 stop26h 03m

Port of Spain Piarco Intl

Sun 5/17

9:10 am-11:59 pm

1 stop15h 49m

$484

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 3/29

9:50 am-12:20 am

1 stop13h 30m

Port of Spain Piarco Intl

Tue 3/31

2:40 pm-8:05 am

2 stops18h 25m

$499

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 3/13

6:04 pm-12:20 am

2 stops53h 16m

Port of Spain Piarco Intl

Tue 3/17

1:20 am-8:00 am

2 stops31h 40m

$508

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 3/5

6:51 pm-1:20 am

2 stops28h 29m

Port of Spain Piarco Intl

Tue 3/10

9:10 am-7:11 pm

3 stops35h 01m

$522

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

Fri 3/20

1:20 am-3:10 pm

1 stop14h 50m

$528

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

Showing 1-10 of 17 results
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 February.
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 $435). Flying from Chicago O'Hare Intl Airport to Port of Spain in January is currently the most expensive (average of $687). 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 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 February 23, 2026.
Get a feel of what it's like to fly with United Airlines, American Airlines, and Air Canada 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.
United Airlines
7.4
Good
9,342 reviews

Crew

8.1

Boarding

7.7

Comfort

7.3

Overall

7.4

Food

6.6

Entertainment

7.1

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
9,342 reviews
United Airlines
7.4
Good
9,342 reviews

Crew

8.1

Boarding

7.7

Comfort

7.3

Overall

7.4

Food

6.6

Entertainment

7.1

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
11,339 reviews
United Airlines
7.4
Good
9,342 reviews

Crew

8.1

Boarding

7.7

Comfort

7.3

Overall

7.4

Food

6.6

Entertainment

7.1

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
10,739 reviews
United Airlines
7.4
Good
9,342 reviews

Crew

8.1

Boarding

7.7

Comfort

7.3

Overall

7.4

Food

6.6

Entertainment

7.1

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 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 3 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 27h. 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 $432. Additional round-trip tickets that might be worth considering are offered by American Airlines and United Airlines, with the lowest prices starting at $548 and $548, respectively. You may be able to fly from Chicago O'Hare Intl Airport to Port of Spain for 35% 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 $435). Flying from Chicago O'Hare Intl Airport to Port of Spain in January is currently the most expensive (average of $687). 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.

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

Discover the top 3 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 February 23, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$432Average$556FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$548Average$688FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$548Average$628FlexibilityNo cancel feeOn-time69%

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