ORD - POS

$205 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 2/15. 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
$358
Overall average: $669
Air Canada
Fri 2/27Thu 3/5
ORD - POS • 1 stop
Cheapest one-way
$205
Typical prices: $213-$291
Air Canada
Sun 2/15
ORD - POS • 1 stop
Top airlines
Air Canada
Cheapest • from $358 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
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

Fri, Feb 27 - Thu, Mar 5
Air Canada Logo
2:00 pm - 1:20 am
ORD
-
POS
9h 20m
1 stop
Air Canada Logo
2:20 am - 3:10 pm
POS
-
ORD
14h 50m
1 stop
$358Air Canada
Fri, Feb 27 - Thu, Mar 5
Air Canada Logo
2:00 pm - 1:20 am
ORD
-
POS
9h 20m
1 stop
Air Canada Logo
2:20 am - 6:52 pm
POS
-
ORD
42h 32m
2 stops
$368Air Canada
Sun, Mar 8 - Mon, Mar 16
Multiple Airlines Logo
5:15 am - 8:00 pm
ORD
-
POS
13h 45m
1 stop
Multiple Airlines Logo
10:10 am - 7:46 pm
POS
-
ORD
10h 36m
1 stop
$437Multiple Airlines
Wed, Mar 4 - Thu, Mar 12
Multiple Airlines Logo
10:00 am - 7:17 am
ORD
-
POS
19h 17m
2 stops
Multiple Airlines Logo
1:20 am - 7:45 pm
POS
-
ORD
19h 25m
1 stop
$446Multiple Airlines
Sun, Mar 8 - Mon, Mar 16
Multiple Airlines Logo
8:00 am - 12:20 am
ORD
-
POS
15h 20m
1 stop
Multiple Airlines Logo
3:26 pm - 10:10 am
POS
-
ORD
19h 44m
2 stops
$451Multiple Airlines
Wed, Mar 4 - Thu, Mar 12
Air Canada Logo
8:40 pm - 1:20 am
ORD
-
POS
26h 40m
1 stop
Air Canada Logo
1:20 am - 3:10 pm
POS
-
ORD
14h 50m
1 stop
$458Air Canada
Wed, May 6 - Sun, May 10
Air Canada Logo
8:45 am - 12:15 am
ORD
-
POS
14h 30m
2 stops
Air Canada Logo
1:25 am - 1:25 pm
POS
-
ORD
13h 00m
1 stop
$461Air Canada
Wed, Mar 4 - Tue, Mar 10
Air Canada Logo
8:40 pm - 1:20 am
ORD
-
POS
26h 40m
1 stop
Air Canada Logo
1:20 am - 6:52 pm
POS
-
ORD
18h 32m
2 stops
$463Air Canada
Wed, May 6 - Sun, May 10
Air Canada Logo
8:45 am - 12:15 am
ORD
-
POS
14h 30m
2 stops
Air Canada Logo
1:25 am - 6:53 pm
POS
-
ORD
18h 28m
2 stops
$466Air Canada
Wed, Mar 4 - Tue, Mar 10
Air Canada Logo
6:04 pm - 1:20 am
ORD
-
POS
29h 16m
2 stops
Air Canada Logo
1:20 am - 6:52 pm
POS
-
ORD
42h 32m
2 stops
$468Air 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.

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 $767 and $753 respectively.

Good to know

Low seasonApril
Cheapest flight$205
Best time to beat the crowds but there is an average 21% increase in price.
Most popular time to fly with an average 7% 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 $205 for a one-way ticket and $358 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 $641 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 9214 reviews
8.1Crew
7.3Comfort
7.1Entertainment
7.7Boarding
6.6Food
Airline reviews

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

8.0 ExcellentAnonymous, Jan 2026
ORD - TPA
Read more United Airlines reviews

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Not United Airlines' fault. It's ORL airport's fault.

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

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.

The aircraft had several problems - from excess fuel to non operational ac. Two hours of delay in Chicago could have been avoided with proper planning and aircraft maintenance.

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

We were upgraded to First Class and it was a great flight

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

My carry on baggage was damaged. Entire trip, I had to carry the baggage. When complained to the boarding crew, they got mad at me and still asked me to valet check in the cabin baggage. Rude boarding crew!!!

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

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.

The plane was delayed substantially due to a mechanical problem, that being said, the airline was very fair with providing a meal coupon for us. I would rather arrive late on a mechanically sound plane than the alternative. The food served in the plane was just awful, however and I recommend a new catering company.

I waiting for 2 hrs to retrieve my luggage. Didn't get home till 3am.

The flight left late and I didn’t get a glass of bubbly upon boarding (which I’m used to when booking business class on other flights), but otherwise it was a pleasant flight with lovely, helpful crew members and I enjoyed my meal.

Flight cancellations, delays, mass confusion and disorganization! That’s Air Canada for you, nothing new. I would have chosen a different airline if it were an option, and Air Canada continues to prove they don’t care about their customers.

everything was fine. but paying for 1 piece of check-in luggage and denying passengers to board with carry-on luggage which by air line's standards does not fit is not acceptable. when one travels for a longer time one needs to have some essentials

Couldn't fit knees, only 1 toilet working, didn't get anything to drink cause the stewards were not able to get to us

Flight was canceled for a reason they knew hours before but did not mention. Next the gate chnage from 37 to 38 at least 10 times. Ridiculous.

The flight from SFO to YVR was delayed and my bag did not make it to my next flight from YVR to SYD. It took almost 3 days after I landed to get my bag and when I got it, it was filled with dust

Our biggest complaint about Air Canada is that if you don’t like your seat during check-in, there’s a fee to move elsewhere. On our flight from YUL to FFL, we were charged to change seats—just regular seats. What’s maddening is that the plane wasn’t even full; there were even a few people sleeping in the middle row sections (entire rows, completely empty), using them as beds. In my opinion, charging passengers for seat changes is a cash grab by Air Canada. They are definitely not the airline they were back in the day. I suppose they need to gouge the consumer now that they pay their attendants while on ground. One out of 10.

Nothing specific. Cabin temperature was too high for some reason.

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

Information on your arrival and departure airports