ORD - POS

$455 Find Cheap Flights from Chicago to Port of Spain

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Port of Spain departing on 9/16. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Port of Spain

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Port of Spain, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Port of Spain, as well as popular online travel agencies
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Flights Deals

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

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Port of Spain that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Port of Spain

Tue, Sep 16 - Fri, Sep 26
 Logo
10:27 am - 6:55 pmORD-POS
31h 28m1 stop
 Logo
9:10 am - 9:18 amPOS-ORD
25h 08m1 stop
Wed, Oct 22 - Sun, Oct 26
 Logo
5:05 am - 1:46 amORD-POS
19h 41m2 stops
 Logo
6:25 pm - 9:18 amPOS-ORD
15h 53m1 stop
Fri, Sep 19 - Sun, Sep 28
Copa Airlines Logo
3:07 pm - 1:46 amORD-POS
9h 39m1 stop
Copa Airlines Logo
3:51 am - 1:41 pmPOS-ORD
10h 50m1 stop
$526Copa Airlines
Find Deal
Tue, Nov 11 - Fri, Nov 21
Air Canada Logo
10:00 am - 1:15 amORD-POS
13h 15m1 stop
Air Canada Logo
2:15 am - 1:01 pmPOS-ORD
12h 46m1 stop
$537Air Canada
Find Deal
Fri, Sep 19 - Sun, Sep 28
Air Canada Logo
10:40 am - 1:20 amORD-POS
13h 40m2 stops
Air Canada Logo
2:25 am - 6:54 pmPOS-ORD
17h 29m2 stops
$542Air Canada
Find Deal
Fri, Sep 19 - Mon, Sep 29
American Airlines Logo
7:15 pm - 2:16 pmORD-POS
18h 01m1 stop
American Airlines Logo
3:25 pm - 11:49 pmPOS-ORD
9h 24m1 stop
$548American Airlines
Find Deal
Wed, Oct 22 - Sun, Oct 26
American Airlines Logo
5:00 am - 2:25 pmORD-POS
8h 25m1 stop
American Airlines Logo
7:00 am - 10:35 pmPOS-ORD
16h 35m1 stop
$553American Airlines
Find Deal
Wed, Oct 22 - Sat, Oct 25
Copa Airlines Logo
7:53 am - 1:46 amORD-POS
16h 53m1 stop
Copa Airlines Logo
3:51 am - 1:41 pmPOS-ORD
10h 50m1 stop
$564Copa Airlines
Find Deal
Wed, Oct 22 - Sat, Oct 25
United Airlines Logo
12:45 pm - 11:23 pmORD-POS
9h 38m1 stop
United Airlines Logo
12:30 am - 7:56 pmPOS-ORD
20h 26m1 stop
$658United Airlines
Find Deal
Tue, Nov 25 - Sat, Nov 29
United Airlines Logo
12:45 pm - 12:23 amORD-POS
9h 38m1 stop
United Airlines Logo
1:30 am - 12:15 amPOS-ORD
24h 45m1 stop
$669United Airlines
Find Deal
Booking Insights

KAYAK's insights & trends for Chicago to Port of Spain flights

Get data-powered insights and trends into flights from Chicago to Port of Spain to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Chicago to Port of Spain?

The average price of all round-trip flights from Chicago O'Hare Intl Airport to Port of Spain clicked on KAYAK for each day over the last 12 months.

For Chicago to Port of Spain, Sunday is the cheapest day to fly on average and Monday is the most expensive. Flying from Port of Spain back to Chicago, the best deals are generally found on Thursday, with Wednesday being the most expensive.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to Port of Spain, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago O'Hare Intl Airport to Port of Spain is January, where tickets cost $528 (return) on average. On the other hand, the most expensive months are December and April, where the average cost of round-trip tickets is $928 and $777 respectively.

Good to know

Low seasonSeptember
Cheapest flight$455
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly and prices are also 2% lower on average.
Flight from Chicago to Port of Spain

When to book flights from Chicago to Port of Spain

Are your dates flexible? Find out the best times to travel from Chicago to Port of Spain based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago to Port of Spain flights

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

    In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Port of Spain was $553 for a one-way ticket and $455 for a round-trip.

  • Do I need a passport to fly between Chicago and Port of Spain?

    Yes

  • Which airports will I be using when flying from Chicago to Port of Spain?

    When flying out of Chicago you will be using Chicago O'Hare Intl. You will be landing at Port of Spain, also known as Port of Spain Piarco Intl.

  • Which aircraft models fly most regularly from Chicago to Port of Spain?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago to Port of Spain?

    oneworld, and Star Alliance are the airline alliances operating flights between Chicago and Port of Spain, with Star Alliance being the most commonly used for this route.

  • Which is the best airline for flights from Chicago to Port of Spain, United Airlines or American Airlines?

    The two airlines most popular with KAYAK users for flights from Chicago to Port of Spain are United Airlines and American Airlines. With an average price for the route of $628 and an overall rating of 7.4, United Airlines is the most popular choice. American Airlines is also a great choice for the route, with an average price of $605 and an overall rating of 7.2.

  • How does KAYAK find such low prices on flights from Chicago to Port of Spain?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Port of Spain.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Port of Spain?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Port of Spain from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Port of Spain?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Port of Spain with an airline and back to Chicago with another airline. Booking your flights between Chicago and POS can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Port of Spain?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Port of Spain from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Chicago to Port of Spain

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Port of Spain. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Port of Spain? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 8896 reviews
7.3Comfort
7.7Boarding
8.1Crew
7.1Entertainment
6.6Food
Airline reviews

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

10.0 ExcellentAnita, Jul 2025ORD - CMH
Read more United Airlines reviews

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

Everything you need to know for your flight from Chicago to Port of Spain

Information on your arrival and departure airports

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