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Port of Spain

$306+ 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 1/5. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — POS
Aug 23 — Aug 301
Sat 8/23
Sat 8/30
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 August 18, 2025.

Round-trip from

$441
(Kiwi.com)

One-way from

$306
(United Airlines)

Popular in

December

Cheapest in

January

Average price

$645
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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Highest demand for flights based on searches. 2% potential increase in price ($15 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($19 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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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 August 18, 2025.

This Kiwi.com deal was found by Cheapflights users on 8/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2110:27 amORD - POS
1 stop16h 48mMultiple Airlines
Sun 9/286:25 pmPOS - ORD
1 stop15h 53mMultiple Airlines
Deal found 8/14$441
This Kiwi.com deal was found by Cheapflights users on 8/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/256:44 pmORD - POS
1 stop24h 16mMultiple Airlines
Thu 10/26:25 pmPOS - ORD
1 stop15h 53mMultiple Airlines
Deal found 8/15$461
This Kiwi.com deal was found by Cheapflights users on 8/16. 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.
Fri 9/1910:27 amORD - POS
1 stop31h 28mMultiple Airlines
Mon 9/2910:10 amPOS - ORD
1 stop13h 38mMultiple Airlines
Deal found 8/16$463
This Kiwi.com deal was found by Cheapflights users on 8/15. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/195:05 amORD - POS
1 stop13h 55mMultiple Airlines
Sun 10/2610:10 amPOS - ORD
1 stop9h 14mMultiple Airlines
Deal found 8/15$507
This Kiwi.com deal was found by Cheapflights users on 8/17. 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 10/2210:27 amORD - POS
1 stop31h 28mMultiple Airlines
Sun 10/266:25 pmPOS - ORD
1 stop15h 57mMultiple Airlines
Deal found 8/17$516
This Kiwi.com deal was found by Cheapflights users on 8/17. 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.
Tue 10/143:12 pmORD - POS
2 stops29h 08mMultiple Airlines
Wed 10/299:10 amPOS - ORD
1 stop25h 12mMultiple Airlines
Deal found 8/17$518
This Air Canada deal was found by Cheapflights users on 8/16. 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.
Fri 9/192:00 pmORD - POS
1 stop10h 20mAir Canada
Sun 9/282:25 amPOS - ORD
1 stop9h 28mAir Canada
Deal found 8/16$523

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 August 18, 2025.
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

Sun 9/21

10:27 am-4:15 am

1 stop16h 48m

Port of Spain Piarco Intl

Sun 9/28

6:25 pm-9:18 am

1 stop15h 53m

$441

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Thu 9/25

6:44 pm-8:00 pm

1 stop24h 16m

Port of Spain Piarco Intl

Thu 10/2

6:25 pm-9:18 am

1 stop15h 53m

$461

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 9/19

10:27 am-6:55 pm

1 stop31h 28m

Port of Spain Piarco Intl

Mon 9/29

10:10 am-10:48 pm

1 stop13h 38m

$463

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 10/22

7:29 pm-1:46 am

2 stops29h 17m

Port of Spain Piarco Intl

Sun 10/26

6:25 pm-9:22 am

1 stop15h 57m

$498

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 10/19

5:05 am-8:00 pm

1 stop13h 55m

Port of Spain Piarco Intl

Sun 10/26

10:10 am-6:24 pm

1 stop9h 14m

$507

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 1/5

8:54 am-12:23 am

1 stop13h 29m

$306

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 12/17

8:15 pm-1:10 am

1 stop26h 55m

$388

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 12/24

9:23 pm-12:23 am

1 stop25h 00m

$465

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 12/17

7:00 am-10:15 pm

1 stop13h 15m

$553

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 2/11

2:22 pm-1:44 am

1 stop9h 22m

$640

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/15

Showing 1-10 of 11 results
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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, October 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 December is currently the most expensive (average of $710). 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 ORD to POS?

Find hourly flight availability from O'Hare Intl to Port of Spain. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 18, 2025.

It’s optimal to fly from Chicago O'Hare Intl Airport to Port of Spain in the afternoon. By choosing this option you can save up to 42% on the cost of your flight, compared to a flight in the evening.

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 August 18, 2025.
Get a feel of what it's like to fly with United Airlines and American 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.
United Airlines
7.4
Good
8,925 reviews

Food

6.6

Comfort

7.3

Boarding

7.7

Crew

8.1

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??
United Airlines
7.4
Good
8,925 reviews
United Airlines
7.4
Good
8,925 reviews

Food

6.6

Comfort

7.3

Boarding

7.7

Crew

8.1

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??
American Airlines
7.2
Good
10,000 reviews
United Airlines
7.4
Good
8,925 reviews

Food

6.6

Comfort

7.3

Boarding

7.7

Crew

8.1

Entertainment

7.1

Overall

7.4

Reviews

1 / 20
4.0
Okay

Thomas,Mar 2025

SFO - TPE

When I asked for an extra snack, I got an unhappy look from the stewardess. Geez, does one extra snack really affect the bottom line??

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 2 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.

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

    Flying on United Airlines is currently your cheapest option to Port of Spain, with prices starting at $480. Another option worth looking into is American Airlines, starting at $487 round trip. You may be able to fly from Chicago O'Hare Intl Airport to Port of Spain for 24% 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, October 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 December is currently the most expensive (average of $710). 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 2 airlines flying from O'Hare Intl to Port of Spain

Discover the top 2 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 August 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$480Average$626FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$487Average$610FlexibilityNo cancel feeOn-time71%

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