
$251 Cheap American Airlines flights from Chicago to Port of Spain (ORD to POS)
Find The Best Day To Fly from Chicago to Port of Spain
Amazing American Airlines ORD to POS Flight Deals
The cheapest flights to Piarco Intl. found within the past 7 days were $540 round trip and $251 one way. Prices and availability subject to change. Additional terms may apply.
POS From ORD Economy Coach Packages on Similar Airlines



Frequently asked questions
Discover our best American Airlines flight from Chicago ORD to Port of Spain POS
To find the best deals on flights to Chicago from Port of Spain with American Airlines, just enter your travel dates, filter by American Airlines, and hit search. You’ll find flights to choose from and can sort by price, flight duration, and arrival or departure time.
Return flights from Chicago ORD to Port of Spain POS with American Airlines
If you’re planning a round trip, booking return flights with American Airlines is usually the most cost-effective option. With airfares ranging from $540 to $549, it’s easy to find a flight that suits your budget. Prices and availability subject to change. Additional terms may apply.
Book one-way American Airlines flights from Chicago ORD to Port of Spain POS
A one-way ticket gives you much greater flexibility—allowing you to choose your return date, destination, and time whenever you’re ready. By booking in advance you can find great deals on one-way tickets too. Right now, a one-way American Airlines flight from Chicago to Port of Spain costs from $251. Prices and availability subject to change. Additional terms may apply.
The easy way to find cheap flights to Port of Spain POS from Chicago ORD with American Airlines
To find a cheap American Airlines flight from Chicago ORD to Port of Spain POS, sort your search results by price or filter by budget. Thanks to Travelocity’s Price Match Promise, if you find a better airfare deal anywhere else within 24 hours, we’ll credit or refund the difference.
How to find our best airfare deals on American Airlines flights from Chicago ORD to Port of Spain POS
If you’re looking for cheap flights, it helps to be flexible when it comes to your travel dates. You’ll usually find lower cost tickets when you travel during quieter months such as March, or if you book a flight with a stopover.
Find nonstop flights from Chicago ORD to Port of Spain POS with American Airlines
If you’re keen to be on Port of Spain soil fast, don’t waste time with a stopover—filter your search results to show direct American Airlines flights only. The journey takes around hour(s) min(s) – so you’ll be there before you know it.
Flexible airline tickets for American Airlines flights from Chicago ORD to Port of Spain POS
Make sure you’re not out of pocket if plans change by choosing a flexible ticket with penalty-free amendment and cancellation options. Use our ‘no change fee’ filter to see which flights have this option.
There are a lot of reasons to book your flights to Port of Spain POS from Chicago ORD with American Airlines on Travelocity
At Travelocity our vast and up-to-the-minute inventory puts all of our best flight deals in one place. So, whether you’re traveling on business or jetting off with friends and family, you can trust Travelocity to get you there.
Airport code | Country | Airport name | Number of flights |
|---|---|---|---|
| DFW | USA | Dallas-Fort Worth Intl. | 599 |
| CLT | USA | Charlotte-Douglas Intl. | 536 |
| ORD | USA | O'Hare Intl. | 317 |
| PHL | USA | Philadelphia Intl. | 247 |
| MIA | USA | Miami Intl. | 193 |
| DCA | USA | Ronald Reagan Washington National | 152 |
| PHX | USA | Sky Harbor Intl. | 141 |
| LAX | USA | Los Angeles Intl. | 81 |
| LGA | USA | LaGuardia | 72 |
| BOS | USA | Logan Intl. | 57 |
Travelers ❤️ these 🏨 after their flight to Port of Spain

Regent Star Hotel
We stayed at the Regent Star overnight for a layover and we had a very pleasant experience. The shuttle to the from the airport was very convenient, the breakfast was good, and they allowed us a late checkout which was wonderful. The bed was a little firmer than we like, but we had a good night of ...
Reviewed on Sep 6, 2025

Airport Suites Hotel
good stay for overnight transits
Reviewed on Oct 22, 2025

Holiday Inn Express Hotel & Suites Trincity Trinidad Airport by IHG
Room was clean, staff was amazing, everyone but Noel from transport, he was rude and unreliable. Wifi was good, pool was perfect, buffet breakfast was delicious. Offere traditional foods and ethnic. Perfect blend. Location was geat, close to tons of food options as well as the mall.
Reviewed on Oct 25, 2025
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