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Port of Spain

$182+ 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 2/28. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — POS
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
1 adult, Economy
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Cheap 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 January 8, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$371
(Expedia)

One-way from

$182
(Kiwi.com)

Popular in

December

Cheapest in

November

Average price

$528
Provider with most accurate pricing for Chicago O'Hare Intl-Port of Spain Piarco Intl flight deals.
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Provider most trusted by Cheapflights users for Chicago O'Hare Intl-Port of Spain Piarco Intl flights.
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From Chicago O'Hare Intl to Port of Spain Piarco Intl
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One-way flight from Chicago O'Hare Intl to Port of Spain Piarco Intl
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High demand for flights, 7% potential price rise
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Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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Find 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 January 8, 2026.

This Expedia deal was found by Cheapflights users on 1/7. 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.
Thu 3/510:00 amORD - POS
2 stops19h 17mJetBlue
Mon 3/98:05 amPOS - ORD
2 stops26h 04mJetBlue
Deal found 1/7$371
This Air Canada deal was found by Cheapflights users on 1/8. 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 1/268:45 pmORD - POS
1 stop26h 35mAir Canada
Sun 2/12:20 amPOS - ORD
1 stop12h 41mAir Canada
Deal found 1/8$417
This Air Canada deal was found by Cheapflights users on 1/6. 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.
Wed 1/218:45 pmORD - POS
1 stop26h 35mAir Canada
Fri 1/232:20 amPOS - ORD
1 stop19h 25mAir Canada
Deal found 1/6$427
This Air Canada deal was found by Cheapflights users on 1/7. 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 1/108:30 pmORD - POS
1 stop26h 50mAir Canada
Tue 1/132:20 amPOS - ORD
2 stops14h 35mAir Canada
Deal found 1/7$436
This Expedia deal was found by Cheapflights users on 1/7. 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.
Sun 1/258:00 amORD - POS
1 stop15h 20mMultiple Airlines
Sun 2/18:20 amPOS - ORD
2 stops35h 23mMultiple Airlines
Deal found 1/7$440
This Expedia deal was found by Cheapflights users on 1/7. 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.
Sun 1/257:45 amORD - POS
2 stops33h 26mJetBlue
Sun 2/18:20 amPOS - ORD
2 stops35h 23mJetBlue
Deal found 1/7$444
This FlightHub deal was found by Cheapflights users on 1/6. 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.
Sun 3/228:00 amORD - POS
1 stop15h 20mMultiple Airlines
Mon 3/233:26 pmPOS - ORD
2 stops19h 39mMultiple Airlines
Deal found 1/6$446
This Air Canada deal was found by Cheapflights users on 1/7. 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.
Thu 3/1210:00 amORD - POS
1 stop13h 20mAir Canada
Tue 3/171:20 amPOS - ORD
1 stop12h 41mAir Canada
Deal found 1/7$447

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 January 8, 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 1/26

8:45 pm-1:20 am

1 stop26h 35m

Port of Spain Piarco Intl

Sun 2/1

2:20 am-1:01 pm

1 stop12h 41m

$417

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 3/21

8:40 pm-12:20 am

1 stop26h 40m

Port of Spain Piarco Intl

Fri 3/27

1:20 am-2:55 pm

2 stops14h 35m

$421

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 1/21

8:45 pm-1:20 am

1 stop26h 35m

Port of Spain Piarco Intl

Fri 1/23

2:20 am-7:45 pm

1 stop19h 25m

$427

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 1/25

8:00 am-1:20 am

1 stop15h 20m

Port of Spain Piarco Intl

Sun 2/1

8:20 am-5:43 pm

2 stops35h 23m

$441

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 1/25

7:45 am-7:11 pm

2 stops33h 26m

Port of Spain Piarco Intl

Sun 2/1

8:20 am-5:43 pm

2 stops35h 23m

$444

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 3/22

8:00 am-12:20 am

1 stop15h 20m

Port of Spain Piarco Intl

Mon 3/23

3:26 pm-10:05 am

2 stops19h 39m

$446

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 3/13

10:00 am-12:20 am

1 stop13h 20m

Port of Spain Piarco Intl

Tue 3/17

1:20 am-3:10 pm

1 stop14h 50m

$447

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 3/12

2:00 pm-12:20 am

1 stop9h 20m

Port of Spain Piarco Intl

Tue 3/17

1:20 am-2:55 pm

2 stops14h 35m

$451

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 2/28

12:06 pm-8:00 pm

1 stop29h 54m

$182

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 2/27

10:00 am-1:20 am

1 stop13h 20m

$185

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/6

Showing 1-10 of 15 results
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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 January.
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 Chicago O'Hare Intl Airport-Port of Spain flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Chicago O'Hare Intl Airport-Port of Spain flight deals on Cheapflights vs. eDreams >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 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 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 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 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 January 8, 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
9,139 reviews

Crew

8.1

Overall

7.4

Food

6.6

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

IAD - TYS

It was a short flight on a small express plane, so no time for amenities. Quickly on, quickly off. No complaints.
United Airlines
7.4
Good
9,139 reviews
United Airlines
7.4
Good
9,139 reviews

Crew

8.1

Overall

7.4

Food

6.6

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

IAD - TYS

It was a short flight on a small express plane, so no time for amenities. Quickly on, quickly off. No complaints.
American Airlines
7.2
Good
11,095 reviews
United Airlines
7.4
Good
9,139 reviews

Crew

8.1

Overall

7.4

Food

6.6

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

IAD - TYS

It was a short flight on a small express plane, so no time for amenities. Quickly on, quickly off. No complaints.
Air Canada
7.1
Good
10,603 reviews
United Airlines
7.4
Good
9,139 reviews

Crew

8.1

Overall

7.4

Food

6.6

Boarding

7.7

Entertainment

7.1

Comfort

7.3

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

IAD - TYS

It was a short flight on a small express plane, so no time for amenities. Quickly on, quickly off. No complaints.

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 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 $432. Additional round-trip tickets that might be worth considering are offered by United Airlines and American Airlines, with the lowest prices starting at $501 and $528, respectively. You may be able to fly from Chicago O'Hare Intl Airport to Port of Spain for 30% 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 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

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Alternative routes for O'Hare Intl to Port of Spain

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Scarborough flights

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 January 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$432Average$556FlexibilityNo cancel feeOn-time67%
American AirlinesCheapest$528Average$637FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$548Average$628FlexibilityNo cancel feeOn-time69%

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