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Port of Spain

$235+ 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 7/25. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — POS
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 June 12, 2025.

Round-trip from

$503
(Booking.com)

One-way from

$235
(Air Canada)

Popular in

December

Cheapest in

January

Average price

$566
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. 1% potential increase in price ($12 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This Booking.com deal was found by Cheapflights users on 6/11. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/268:25 pmORD - POS
1 stop27h 55mAir Canada
Fri 8/12:20 amPOS - ORD
2 stops17h 33mAir Canada
Deal found 6/11$503
This Copa Airlines deal was found by Cheapflights users on 6/10. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/223:07 pmORD - POS
1 stop9h 41mCopa Airlines
Sun 10/264:01 amPOS - ORD
1 stop10h 41mCopa Airlines
Deal found 6/10$511
This JetBlue deal was found by Cheapflights users on 6/11. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/266:16 amORD - POS
1 stop10h 48mJetBlue
Sat 8/28:50 amPOS - ORD
1 stop14h 38mJetBlue
Deal found 6/11$523
This American Airlines deal was found by Cheapflights users on 6/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/145:00 amORD - POS
1 stop8h 00mAmerican Airlines
Tue 8/267:00 amPOS - ORD
1 stop11h 55mAmerican Airlines
Deal found 6/12$548
This Booking.com deal was found by Cheapflights users on 6/12. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/129:55 amORD - POS
1 stop14h 30mMultiple Airlines
Fri 9/1910:10 amPOS - ORD
1 stop29h 24mMultiple Airlines
Deal found 6/12$565
This Trip.com deal was found by Cheapflights users on 6/12. 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.
Fri 9/128:45 amORD - POS
1 stop13h 38mUnited Airlines
Thu 9/1812:30 amPOS - ORD
1 stop20h 28mUnited Airlines
Deal found 6/12$620

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 June 12, 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

Sat 7/26

8:25 pm-1:20 am

1 stop27h 55m

Port of Spain Piarco Intl

Fri 8/1

2:20 am-6:53 pm

2 stops17h 33m

$503

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Wed 10/22

3:07 pm-1:48 am

1 stop9h 41m

Port of Spain Piarco Intl

Sun 10/26

4:01 am-1:42 pm

1 stop10h 41m

$511

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sat 7/26

6:16 am-6:04 pm

1 stop10h 48m

Port of Spain Piarco Intl

Sat 8/2

8:50 am-10:28 pm

1 stop14h 38m

$523

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Mon 7/14

5:00 am-2:00 pm

1 stop8h 00m

Port of Spain Piarco Intl

Tue 8/26

7:00 am-5:55 pm

1 stop11h 55m

$548

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 9/12

9:55 am-1:25 am

1 stop14h 30m

Port of Spain Piarco Intl

Fri 9/19

10:10 am-2:34 pm

1 stop29h 24m

$565

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 9/12

8:45 am-11:23 pm

1 stop13h 38m

Port of Spain Piarco Intl

Thu 9/18

12:30 am-7:58 pm

1 stop20h 28m

$620

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 7/25

3:50 pm-1:20 am

1 stop8h 30m

$235

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 7/27

6:16 am-6:04 pm

1 stop10h 48m

$347

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Fri 7/25

4:37 pm-2:30 pm

3 stops20h 53m

$351

ChicagoPort of Spain

ORD - POS

ORDPOS

Chicago O'Hare Intl

Sun 7/27

4:45 pm-11:23 pm

2 stops29h 38m

$1,269

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/11

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 June 12, 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.

Rainfall in Port of Spain by month

Plan your trip to Port of Spain by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Port of Spain ranges from 1.2 - 9.8 inches per month. June is typically the wettest month, when rainfall can reach 9.8 in. March is typically the driest time to visit Port of Spain when rainfall is around 1.2 in.

Temperature in Port of Spain by month

Plan your trip to Port of Spain by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Port of Spain, use this chart to help with planning. For those seeking warmer temperatures, April is the ideal time of year to visit, when temperatures reach an average of 80.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).

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 June 12, 2025.
To help decide which airline to fly from Chicago to Port of Spain, see what other customers have to say about Copa Airlines, United Airlines and JetBlue. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Copa Airlines
7.5
Good
1,451 reviews

Food

6.8

Boarding

7.8

Crew

8.1

Entertainment

6.8

Comfort

7.4

Overall

7.5

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.
Copa Airlines
7.5
Good
1,451 reviews
Copa Airlines
7.5
Good
1,451 reviews

Food

6.8

Boarding

7.8

Crew

8.1

Entertainment

6.8

Comfort

7.4

Overall

7.5

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.
United Airlines
7.4
Good
8,790 reviews
Copa Airlines
7.5
Good
1,451 reviews

Food

6.8

Boarding

7.8

Crew

8.1

Entertainment

6.8

Comfort

7.4

Overall

7.5

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.
JetBlue
7.3
Good
2,925 reviews
Copa Airlines
7.5
Good
1,451 reviews

Food

6.8

Boarding

7.8

Crew

8.1

Entertainment

6.8

Comfort

7.4

Overall

7.5

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.
American Airlines
7.2
Good
10,000 reviews
Copa Airlines
7.5
Good
1,451 reviews

Food

6.8

Boarding

7.8

Crew

8.1

Entertainment

6.8

Comfort

7.4

Overall

7.5

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.
Air Canada
7.1
Good
9,531 reviews
Copa Airlines
7.5
Good
1,451 reviews

Food

6.8

Boarding

7.8

Crew

8.1

Entertainment

6.8

Comfort

7.4

Overall

7.5

Reviews

1 / 20
4.0
Okay

Paul,Jun 2025

PTY - MIA

The boarding process was terrible. No one followed the group numbers. Everyone got up and stood in the tiles upon landing. People kept getting up during the meal and beverage service to go the bathrooms, the crew had to go back and forth in the isles, the service took forever.

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 Air Canada is currently your cheapest option to Port of Spain, with prices starting at $503. Additional round-trip tickets that might be worth considering are offered by JetBlue and American Airlines, with the lowest prices starting at $523 and $548, respectively. You may be able to fly from Chicago O'Hare Intl Airport to Port of Spain for 22% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Chicago O'Hare Intl Airport to Port of Spain one-way?

    For one-way options, check prices for Air Canada. According to our data, you can fly for as low as $235. Users have also found prices from $347 and $1,269 on JetBlue and United Airlines, respectively.

  • 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$480Average$628FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$487Average$634FlexibilityNo cancel feeOn-time71%

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