$260 Cheap Flights from Port of Spain (POS) to Chicago (ORD)

View $260 flight on Sat, Nov 29, 2025Opens in a new window

Popular airlines from Piarco Intl. Airport (POS) to Chicago O'Hare Intl. Airport (ORD)

Cheap Flights from Port of Spain to Chicago (POS-ORD)

Prices were available within the past 7 days and start at $260 for one-way flights and $471 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Tue, Sep 23 - Sat, Sep 27
POS
Trinidad
ORD
Chicago
$471 Roundtrip, found 1 hour ago
$471
Roundtrip
found 1 hour ago
Select Air Canada flight, departing Tue, Sep 23 from Trinidad to Chicago, returning Sat, Sep 27, priced at $471 found 1 hour ago
Air Canada
Sat, Nov 1 - Wed, Nov 5
POS
Trinidad
ORD
Chicago
$485 Roundtrip, found 6 days ago
$485
Roundtrip
found 6 days ago
Select Air Canada flight, departing Sat, Nov 1 from Trinidad to Chicago, returning Wed, Nov 5, priced at $485 found 6 days ago
JetBlue Airways
Fri, Nov 7 - Wed, Nov 12
POS
Trinidad
ORD
Chicago
$487 Roundtrip, found 4 days ago
$487
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Fri, Nov 7 from Trinidad to Chicago, returning Wed, Nov 12, priced at $487 found 4 days ago
JetBlue Airways
Mon, Nov 3 - Sun, Nov 16
POS
Trinidad
ORD
Chicago
$488 Roundtrip, found 1 day ago
$488
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Mon, Nov 3 from Trinidad to Chicago, returning Sun, Nov 16, priced at $488 found 1 day ago
Air Canada
Sat, Sep 27 - Mon, Sep 29
POS
Trinidad
ORD
Chicago
$495 Roundtrip, found 5 days ago
$495
Roundtrip
found 5 days ago
Select Air Canada flight, departing Sat, Sep 27 from Trinidad to Chicago, returning Mon, Sep 29, priced at $495 found 5 days ago
Air Canada
Sat, Oct 25 - Sat, Nov 1
POS
Trinidad
ORD
Chicago
$497 Roundtrip, found 16 hours ago
$497
Roundtrip
found 16 hours ago
Select Air Canada flight, departing Sat, Oct 25 from Trinidad to Chicago, returning Sat, Nov 1, priced at $497 found 16 hours ago
JetBlue Airways
Tue, Oct 21 - Sat, Nov 1
POS
Trinidad
ORD
Chicago
$498 Roundtrip, found 6 days ago
$498
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Tue, Oct 21 from Trinidad to Chicago, returning Sat, Nov 1, priced at $498 found 6 days ago
Copa
Wed, Nov 12 - Mon, Nov 24
POS
Trinidad
ORD
Chicago
$499 Roundtrip, found 4 days ago
$499
Roundtrip
found 4 days ago
Select Copa flight, departing Wed, Nov 12 from Trinidad to Chicago, returning Mon, Nov 24, priced at $499 found 4 days ago
American Airlines
Fri, Oct 17 - Sun, Oct 19
POS
Trinidad
ORD
Chicago
$506 Roundtrip, found 13 hours ago
$506
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Fri, Oct 17 from Trinidad to Chicago, returning Sun, Oct 19, priced at $506 found 13 hours ago
United
Sun, Jan 11 - Thu, Jan 15
POS
Trinidad
ORD
Chicago
$514 Roundtrip, found 1 day ago
$514
Roundtrip
found 1 day ago
Select United flight, departing Sun, Jan 11 from Trinidad to Chicago, returning Thu, Jan 15, priced at $514 found 1 day ago

Find the cheapest month to fly from Piarco (POS) to Chicago (ORD)

September is typically the cheapest month to fly

From $473 - $769 per traveler.

Frequently asked questions

How much does a flight from Piarco Intl. Airport (POS) to O'Hare Intl. Airport (ORD) cost?
Get a cheap one-way flight from $260 or cheap return flight from $471 from Piarco Intl. Airport (POS) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Piarco Intl. Airport (POS) to O'Hare Intl. Airport (ORD)?
Flying in September can help you save, as it's the cheapest month for flights between POS and ORD. You'll often find the lowest fares during off-peak months.
What is the cheapest airline that flies from Piarco Intl. Airport (POS) to O'Hare Intl. Airport (ORD)?
To find the cheapest airline flying from POS to ORD, use Expedia's filter tool. Customize your search based on what's important to you, such as preferred carriers and ideal departure window. You can then sort your results by "Price (lowest to highest)" to see the cheapest fares upfront.
How many flights per day from Piarco Intl. Airport (POS) to O'Hare Intl. Airport (ORD)?
There aren't any daily direct flights from Piarco Intl. Airport (POS) to O'Hare Intl. Airport (ORD). But you can book flights with layovers. Filter your search results on Expedia to include one or more stops, and you'll be cruising above the clouds in no time at all.
What day of the week has the most flights from POS to ORD?
You'll typically find Tuesday the quietest day for flights, while Fridays tend to be the busiest.* However this can vary from season to season and during public holidays or peak travel times.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Piarco Intl. Airport (POS) to O'Hare Intl. Airport (ORD)?
To reach O'Hare Intl. Airport (ORD) on schedule, choose a flight that leaves from Piarco Intl. Airport (POS) before 3 PM. The chance of cancellations is 22% higher, on average, for departures after this hour.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Piarco Intl. Airport (POS) to O'Hare Intl. Airport (ORD) last-minute?
Booking your ticket from POS to ORD just before your getaway is typically more expensive. But if you're flexible with your schedule, you could snag a cheap last-minute fare.
Is it cheaper to book a POS to ORD flight and hotel package?
Compared with arranging flights and hotels separately, booking a POS to ORD flight and hotel package with Expedia could result in significant savings. Better still, having everything in one convenient place will take the hassle out of travel planning. Just secure your flights and choose from our wide range of stays, then tailor your trip with other add-ons like car rentals and activities.
Can I cancel or change the date of my flight from Piarco Intl. Airport (POS) to O'Hare Intl. Airport (ORD)?
If you booked your POS to ORD flight within the last 24 hours, you may be able to modify or cancel it without fees. Depending on the airline and the type of fare you purchased, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal for more details.

Travel information

Travel information

Origin airport
Piarco Intl.
Destination airport
O'Hare Intl.
Airlines serving
Air Canada, American Airlines, Copa, JetBlue Airways, United
Roundtrip price
$471
Distance
2697 mi

Book with confidence

Book with confidence

Port of Spain to Chicago Flights

The cheapest times to fly from Port of Spain to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Port of Spain to Chicago are during the month of September. You can find some of the cheapest flights from Port of Spain to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Port of Spain to Chicago

Sunday is one of the best days to book for cheap flights from Port of Spain to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Port of Spain to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Port of Spain to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $260 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Port of Spain to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Port of Spain to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Port of Spain to Chicago Flights

Explore a world of travel with Expedia

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*Available to One Key members.