HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
O'Hare Intl

$255+ Cheap flights from Port of Spain (POS) to O'Hare Intl (ORD)

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 5/26. Fares are subject to change and may not be available on all flights or dates of travel.
POS — ORD
May 12 — May 191
Mon 5/12
Mon 5/19
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Port of Spain to O'Hare Intl with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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

Discover tips and strategies to find the most affordable flight options for your journey from Port of Spain (POS) to O'Hare Intl (ORD). 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 May 7, 2025.

Most accurate provider

AranGrant
3 stars

Most trusted provider

AranGrant
3 stars

Round-trip from

$513
(Mytrip)

One-way from

$255
(Kiwi.com)

Popular in

April

Cheapest in

February

Average price

$662
Provider with most accurate pricing for Port of Spain Piarco Intl-Chicago O'Hare Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Port of Spain Piarco Intl-Chicago O'Hare Intl flights.
Search Deals
From Port of Spain Piarco Intl to Chicago O'Hare Intl
Search Deals
One-way flight from Port of Spain Piarco Intl to Chicago O'Hare Intl
Search Deals
Highest demand for flights based on searches. 22% potential increase in price ($200 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 10% potential price decrease ($70 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 2025
Search Deals

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

Cheapest flights from Port of Spain to O'Hare Intl
Explore the most affordable flight options available from Port of Spain to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 7, 2025.

This Mytrip deal was found by Cheapflights users on 5/6. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/2010:10 amPOS - ORD
1 stop23h 40mMultiple Airlines
Fri 6/2710:00 amORD - POS
1 stop14h 25mMultiple Airlines
Deal found 5/6$513
This Priceline deal was found by Cheapflights users on 5/7. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/302:25 amPOS - ORD
1 stop13h 40mAir Canada
Mon 6/93:50 pmORD - POS
1 stop8h 35mAir Canada
Deal found 5/7$523
This Copa Airlines deal was found by Cheapflights users on 5/7. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/23:44 amPOS - ORD
1 stop11h 03mCopa Airlines
Tue 6/103:07 pmORD - POS
1 stop9h 40mCopa Airlines
Deal found 5/7$551
This United Airlines deal was found by Cheapflights users on 5/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1912:30 amPOS - ORD
1 stop20h 25mUnited Airlines
Fri 6/279:50 pmORD - POS
1 stop24h 33mUnited Airlines
Deal found 5/6$561
This American Airlines deal was found by Cheapflights users on 5/7. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/27:09 amPOS - ORD
1 stop15h 01mAmerican Airlines
Wed 8/137:05 pmORD - POS
1 stop18h 19mAmerican Airlines
Deal found 5/7$563
This JetBlue deal was found by Cheapflights users on 5/7. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/109:22 amPOS - ORD
1 stop14h 06mJetBlue
Sun 7/136:00 amORD - POS
1 stop11h 24mJetBlue
Deal found 5/7$1,027

Cheapflights Fare Finder

Customize your flight search to find flights from Port of Spain to O'Hare Intl 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 May 7, 2025.
Use the filters below to find and compare flights from Port of Spain to Chicago O'Hare Intl Airport that are best for you.

Fly from

Port of Spain

Fly to

O'Hare Intl

Route

Depart

Return

Price

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 6/20

10:10 am-8:50 am

1 stop23h 40m

Chicago O'Hare Intl

Fri 6/27

10:00 am-1:25 am

1 stop14h 25m

$513

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Fri 5/30

2:25 am-3:05 pm

1 stop13h 40m

Chicago O'Hare Intl

Mon 6/9

3:50 pm-1:25 am

1 stop8h 35m

$523

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Mon 6/2

3:44 am-1:47 pm

1 stop11h 03m

Chicago O'Hare Intl

Tue 6/10

3:07 pm-1:47 am

1 stop9h 40m

$551

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 6/19

12:30 am-7:55 pm

1 stop20h 25m

Chicago O'Hare Intl

Fri 6/27

9:50 pm-11:23 pm

1 stop24h 33m

$561

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Wed 7/2

7:09 am-9:10 pm

1 stop15h 01m

Chicago O'Hare Intl

Wed 8/13

7:05 pm-2:24 pm

1 stop18h 19m

$563

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 7/10

9:22 am-10:28 pm

1 stop14h 06m

Chicago O'Hare Intl

Sun 7/13

6:00 am-6:24 pm

1 stop11h 24m

$1,027

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Mon 5/26

3:44 am-5:41 pm

2 stops38h 57m

$255

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Mon 5/26

2:25 am-10:54 am

1 stop9h 29m

$288

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Tue 7/8

3:48 am-1:42 pm

1 stop10h 54m

$299

Port of SpainChicago

POS - ORD

POSORD

Port of Spain Piarco Intl

Thu 6/19

12:30 am-5:10 pm

1 stop17h 40m

$308

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/6

Showing 1-10 of 11 results
1
2

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

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 Port of Spain to O'Hare Intl in May.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*2 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
AranGrantPrice Accuracy3 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 Port of Spain-Chicago O'Hare Intl Airport flights, users find the pricing of AranGrant to be most consistent on Cheapflights vs. AranGrant Users can find the same prices on Port of Spain-Chicago O'Hare Intl Airport flight deals on Cheapflights vs. AranGrant >95% of the time. Price accuracy is based on data collected from Port of Spain-Chicago O'Hare Intl Airport flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Port of Spain-Chicago O'Hare Intl Airport flights, Cheapflights users trust AranGrant the most. AranGrant 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 Port of Spain-Chicago O'Hare Intl Airport 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 Port of Spain to O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from Port of Spain 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 Port of Spain to Chicago O'Hare Intl Airport

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

Currently, August is the cheapest month in which you can book a flight from Port of Spain to Chicago O'Hare Intl Airport (average of $245). Flying from Port of Spain to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $321). 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 POS to ORD?

Find hourly flight availability from Port of Spain to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated May 7, 2025.

Unlike at noon, when flights are generally more expensive, you can save up to 6% on flights from Port of Spain to Chicago O'Hare Intl Airport by exploring options for tickets in the morning.

Rainfall in O'Hare Intl by month

Plan your trip to O'Hare Intl by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago O'Hare Intl Airport ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago O'Hare Intl Airport when rainfall is around 1.7 in.

Temperature in O'Hare Intl by month

Plan your trip to O'Hare Intl by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago O'Hare Intl Airport, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing O'Hare Intl

Get insights into the airlines that provide service to O'Hare Intl. 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 O'Hare Intl. Reviews last updated May 7, 2025.
Copa Airlines
7.5
Good
1,418 reviews

Overall

7.5

Boarding

7.8

Entertainment

6.8

Food

6.8

Comfort

7.4

Crew

8.1

Reviews

1 / 20
4.0
Okay

Anonymous,Mar 2025

PTY - JFK

There was no chance for me to choose a seat even if I were willing to pay extra for it when I was doing the check-in on line. My seats were the last row on the plane and they didn't have enough food to give me. I had to eat what was left after everybody else had their choice of food. This is unacceptable. Everyone should have a choice. I paid money just like everybody else. Never had this happened on any other airlines even if my seats were last row on the plane.
Copa Airlines
7.5
Good
1,418 reviews
Copa Airlines
7.5
Good
1,418 reviews

Overall

7.5

Boarding

7.8

Entertainment

6.8

Food

6.8

Comfort

7.4

Crew

8.1

Reviews

1 / 20
4.0
Okay

Anonymous,Mar 2025

PTY - JFK

There was no chance for me to choose a seat even if I were willing to pay extra for it when I was doing the check-in on line. My seats were the last row on the plane and they didn't have enough food to give me. I had to eat what was left after everybody else had their choice of food. This is unacceptable. Everyone should have a choice. I paid money just like everybody else. Never had this happened on any other airlines even if my seats were last row on the plane.
United Airlines
7.4
Good
8,710 reviews
Copa Airlines
7.5
Good
1,418 reviews

Overall

7.5

Boarding

7.8

Entertainment

6.8

Food

6.8

Comfort

7.4

Crew

8.1

Reviews

1 / 20
4.0
Okay

Anonymous,Mar 2025

PTY - JFK

There was no chance for me to choose a seat even if I were willing to pay extra for it when I was doing the check-in on line. My seats were the last row on the plane and they didn't have enough food to give me. I had to eat what was left after everybody else had their choice of food. This is unacceptable. Everyone should have a choice. I paid money just like everybody else. Never had this happened on any other airlines even if my seats were last row on the plane.
JetBlue
7.3
Good
2,922 reviews
Copa Airlines
7.5
Good
1,418 reviews

Overall

7.5

Boarding

7.8

Entertainment

6.8

Food

6.8

Comfort

7.4

Crew

8.1

Reviews

1 / 20
4.0
Okay

Anonymous,Mar 2025

PTY - JFK

There was no chance for me to choose a seat even if I were willing to pay extra for it when I was doing the check-in on line. My seats were the last row on the plane and they didn't have enough food to give me. I had to eat what was left after everybody else had their choice of food. This is unacceptable. Everyone should have a choice. I paid money just like everybody else. Never had this happened on any other airlines even if my seats were last row on the plane.
American Airlines
7.2
Good
10,000 reviews
Copa Airlines
7.5
Good
1,418 reviews

Overall

7.5

Boarding

7.8

Entertainment

6.8

Food

6.8

Comfort

7.4

Crew

8.1

Reviews

1 / 20
4.0
Okay

Anonymous,Mar 2025

PTY - JFK

There was no chance for me to choose a seat even if I were willing to pay extra for it when I was doing the check-in on line. My seats were the last row on the plane and they didn't have enough food to give me. I had to eat what was left after everybody else had their choice of food. This is unacceptable. Everyone should have a choice. I paid money just like everybody else. Never had this happened on any other airlines even if my seats were last row on the plane.
Air Canada
7.0
Good
9,282 reviews
Copa Airlines
7.5
Good
1,418 reviews

Overall

7.5

Boarding

7.8

Entertainment

6.8

Food

6.8

Comfort

7.4

Crew

8.1

Reviews

1 / 20
4.0
Okay

Anonymous,Mar 2025

PTY - JFK

There was no chance for me to choose a seat even if I were willing to pay extra for it when I was doing the check-in on line. My seats were the last row on the plane and they didn't have enough food to give me. I had to eat what was left after everybody else had their choice of food. This is unacceptable. Everyone should have a choice. I paid money just like everybody else. Never had this happened on any other airlines even if my seats were last row on the plane.

Related info for your journey

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

    Port of Spain Piarco Intl (POS), located 12.6 mi from the city center, is the airport you fly out of when you book flights from Port of Spain to Chicago O'Hare Intl. 2 airlines have flights from Piarco Intl to Chicago O'Hare Intl on a regular basis. Booking flights from Port of Spain Piarco Intl to Chicago O'Hare Intl should not be difficult; the airport handles an average of 0 outbound flights to Chicago O'Hare Intl per day.

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

    Cheapflights users have booked flights from Port of Spain to Chicago O'Hare Intl Airport round-trip from $523. Other airlines that can offer you cheap pricing are Copa Airlines, from $551, and United Airlines, from $561. Air Canada is 26% cheaper than the average price of flights available within the next 90 days to this destination.

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

    To fly one-way, consider booking your trip with Air Canada, which is currently one of the cheapest options available, starting at $288. Copa Airlines flights start at $299 while deals on United Airlines start at $308 one-way.

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

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

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

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Port of Spain to O'Hare Intl.

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

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

    Currently, August is the cheapest month in which you can book a flight from Port of Spain to Chicago O'Hare Intl Airport (average of $245). Flying from Port of Spain to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $321). 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

Traveling to a place near Port of Spain?

Book flights to Port of Spain if you plan to visit one of these locations
Schaumburg
Hoffman Estates
Rosemont
Racine
Beloit
Skokie
Naperville
Elgin
Kenosha
Rockford
Tinley Park
Arlington Heights
Orland Park
Joliet
Merrillville
Northbrook
Glenview
Des Plaines
Lake Geneva
Waukegan

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.

Top 2 airlines flying from Port of Spain to O'Hare Intl

Discover the top 2 airlines that operate flights from Port of Spain to O'Hare Intl. 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 May 7, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$493Average$608FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$561Average$662FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.