ORD - POS

$198 Find Cheap Flights from Chicago to Port of Spain

This is the cheapest one-way 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 5/9. 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, 0 bags

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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Everything you should know

Cheapest round-trip
$400
Typical prices: $573-$856
JetBlue
Thu 2/26Tue 3/3
ORD - POS • 2 stops
Cheapest one-way
$198
Air Canada
Sat 5/9
ORD - POS • 1 stop
When to travel
November
Cheapest • 29% price drop
February
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Port of Spain!
Flight Deals
Booking Insights
Flight 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

Thu, Feb 26 - Tue, Mar 3
JetBlue Logo
10:00 am - 7:17 am
ORD
-
POS
19h 17m2 stops
JetBlue Logo
9:05 am - 9:10 am
POS
-
ORD
26h 05m2 stops
$400JetBlue
Thu, Jan 15 - Sun, Jan 18
Multiple Airlines Logo
5:15 am - 8:00 pm
ORD
-
POS
12h 45m1 stop
Multiple Airlines Logo
10:10 am - 8:57 pm
POS
-
ORD
12h 47m1 stop
$431Multiple Airlines
Wed, Jan 14 - Mon, Jan 19
Multiple Airlines Logo
9:23 am - 6:55 pm
ORD
-
POS
31h 32m1 stop
Multiple Airlines Logo
9:10 am - 8:18 am
POS
-
ORD
25h 08m1 stop
$434Multiple Airlines
Fri, Jan 30 - Fri, Feb 6
Multiple Airlines Logo
7:20 am - 8:00 pm
ORD
-
POS
10h 40m1 stop
Multiple Airlines Logo
10:10 am - 7:38 pm
POS
-
ORD
11h 28m1 stop
$435Multiple Airlines
Thu, Jan 15 - Mon, Jan 19
Multiple Airlines Logo
5:15 am - 8:00 pm
ORD
-
POS
12h 45m1 stop
Multiple Airlines Logo
9:10 am - 8:18 am
POS
-
ORD
25h 08m1 stop
$439Multiple Airlines
Wed, Jan 14 - Sun, Jan 18
Multiple Airlines Logo
9:23 am - 6:55 pm
ORD
-
POS
31h 32m1 stop
Multiple Airlines Logo
10:10 am - 8:57 pm
POS
-
ORD
12h 47m1 stop
$440Multiple Airlines
Fri, Feb 6 - Tue, Feb 10
Air Canada Logo
2:00 pm - 1:20 am
ORD
-
POS
9h 20m1 stop
Air Canada Logo
2:20 am - 3:10 pm
POS
-
ORD
14h 50m1 stop
$443Air Canada
Thu, Feb 26 - Tue, Mar 3
JetBlue Logo
12:41 pm - 7:17 am
ORD
-
POS
16h 36m1 stop
JetBlue Logo
9:05 am - 9:10 am
POS
-
ORD
26h 05m2 stops
$445JetBlue
Fri, Jan 30 - Fri, Feb 6
Multiple Airlines Logo
7:15 am - 1:20 am
ORD
-
POS
16h 05m2 stops
Multiple Airlines Logo
8:30 am - 5:44 pm
POS
-
ORD
35h 14m2 stops
$446Multiple Airlines
Thu, Jan 15 - Fri, Jan 16
Air Canada Logo
7:15 am - 1:20 am
ORD
-
POS
16h 05m2 stops
Air Canada Logo
2:20 am - 6:55 pm
POS
-
ORD
18h 35m2 stops
$447Air Canada
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.

How much is a round-trip flight from Chicago O'Hare Intl Airport to Port of Spain?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago O'Hare Intl Airport to Port of Spain departing in February.

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 November, where tickets cost $443 (return) on average. On the other hand, the most expensive months are December and April, where the average cost of round-trip tickets is $822 and $753 respectively.

Good to know

Low seasonApril
Cheapest flight$198
Best time to beat the crowds but there is an average 21% increase in price.
Most popular time to fly with an average 5% increase in price.
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 $198 for a one-way ticket and $400 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?

    Star Alliance, and oneworld 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 $634 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 3 airlines serving 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 9094 reviews
6.6Food
7.7Boarding
7.3Comfort
7.1Entertainment
8.1Crew
Airline reviews

The movies offered were great. Staff were very pleasant and very efficient.

10.0 ExcellentAnonymous, Dec 2025
ORD - HND
Read more United Airlines reviews

The movies offered were great. Staff were very pleasant and very efficient.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very nice flight love the small aircraft. We had a wonderful flight attendant. Nice to see someone that really enjoys her job. Don't have her name but had a southern accent.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Seats in waiting area and on plane hard as rock. Fast internet on the flight was great! Crew was kind.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

Other than a way way too cold cabinets for the entire flight, all was great

One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

My wife and I love to travel, so we fly a lot. We've already logged 381,075 miles and with practically every major airline. But this flight was very disappointing. It started off well, with no delays and a new plane. But when lunchtime approached, all that good impression was ruined. Instead of white tablecloths, we were offered small, dark placemats, which, as it turned out, were perfectly adequate for the food. All the food offered—and my wife and I only took fish, and the meat—was not just bad, it was downright disgusting and not heated enough. The same applies to the appetizers. This was the first time in many years of traveling that we've been offered such disgusting food.

Lost luggage stuck no clothes and no word after 2 days leaving on cruise no stuff or clothes

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

It was just fine. I managed to make all my connection too sbut had trouble in Munich with no wheel chair and trouble trying to get help from the airport people to get to the other terminal for my flight. Finally a wonderful lady Amelia, helped me to make my flight connection Timon with zero time to spare.

Over 40 years ago my AC return flight was canceled, during this last summer the same thing happened. AC denied everything Canadian like paying for accommodations and basic necessities. So why would I ever want to fly AC again? This last flight my wife took the return flight had problems and left late, so I guess they are getting better. However I have no faith in this airline so I drove to this last destination! I'll never fly AC again!!!

Great check in process in LA and good service The check in process as well as at the gate is way better in the US versus canada 🇨🇦

Super experience. Earlier than schedule departure and arrival. Baggage handling was very good

Allow me to book extra bag check in as free though I packed in 1 luggage but that was 7 LBS overweight so make another bag to free check in.

I would like to get my money back. I flight was 4 hours late on the way to detroit, And same on my way back to Brussels they cancelled my flight and give me an other ticket and i had to wait 5 hours.

All attendents were very efficient, pleasant and happy. Everything went smoothly. The seats could have been wider. There could have been more free food instead of just one small bar.

My seat was one of those that couldn't recline, but the problem was that it was abnormally upright, so the headrest actually made the seat concave, which was uncomfortable and hard on my lower back. I had to ball my jacket up and use it as lumbar support. goodness I had it with me.

Boarding was so so after zone 3 was called all other zones went in

I liked a lot , the flight attendant so nice ,the seat very comfortable I enjoyed the flight , I will do it again with Air Canada,

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

Information on your arrival and departure airports