POS - ORD

$253 Find Cheap Flights from Port of Spain to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Port of Spain to Chicago departing on 6/8. 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 Chicago O'Hare Intl Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Port of Spain to Chicago, 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 Port of Spain to Chicago, as well as popular online travel agencies
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41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$528
Typical prices: $530-$376
Multiple Airlines
Mon 6/8Mon 6/15
POS - ORD • 1 stop
Cheapest one-way
$253
Multiple Airlines
Mon 6/8
POS - ORD • 1 stop
Top airlines
Cheapest • from $646 (round-trip)
Best reviews • 7.5 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Port of Spain and Chicago. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $582 (round-trip)
Shortest trip • 10h 40m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 43% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Flight Deals

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

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Port of Spain to Chicago 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 Port of Spain to Chicago

Mon, Jun 8 - Mon, Jun 15
Multiple Airlines Logo
10:10 am - 12:25 pm
POS
-
ORD
27h 15m
1 stop
Multiple Airlines Logo
1:50 pm - 6:55 pm
ORD
-
POS
52h 05m
2 stops
$528Multiple Airlines
Fri, May 15 - Wed, May 20
Multiple Airlines Logo
9:10 am - 11:56 pm
POS
-
ORD
15h 46m
1 stop
Multiple Airlines Logo
1:59 pm - 8:00 pm
ORD
-
POS
29h 01m
2 stops
$535Multiple Airlines
Thu, Jun 11 - Thu, Jun 18
Multiple Airlines Logo
10:10 am - 12:43 pm
POS
-
ORD
27h 33m
1 stop
Multiple Airlines Logo
5:10 am - 8:00 pm
ORD
-
POS
13h 50m
1 stop
$540Multiple Airlines
Mon, Jun 8 - Mon, Jun 15
Multiple Airlines Logo
10:10 am - 12:25 pm
POS
-
ORD
27h 15m
1 stop
Multiple Airlines Logo
5:05 am - 8:00 pm
ORD
-
POS
13h 55m
1 stop
$550Multiple Airlines
Thu, Jun 11 - Thu, Jun 18
Multiple Airlines Logo
9:10 am - 8:03 am
POS
-
ORD
23h 53m
2 stops
Multiple Airlines Logo
5:10 am - 8:00 pm
ORD
-
POS
13h 50m
1 stop
$556Multiple Airlines
Fri, May 29 - Fri, Jul 3
Multiple Airlines Logo
10:10 am - 11:15 pm
POS
-
ORD
14h 05m
1 stop
Multiple Airlines Logo
1:29 pm - 6:55 pm
ORD
-
POS
28h 26m
2 stops
$568Multiple Airlines
Thu, Jun 11 - Thu, Jun 18
Multiple Airlines Logo
10:10 am - 11:30 am
POS
-
ORD
26h 20m
3 stops
Multiple Airlines Logo
5:10 am - 8:00 pm
ORD
-
POS
13h 50m
1 stop
$587Multiple Airlines
Fri, Jun 12 - Fri, Jun 19
Multiple Airlines Logo
10:10 am - 11:15 pm
POS
-
ORD
14h 05m
1 stop
Multiple Airlines Logo
7:52 am - 8:00 pm
ORD
-
POS
11h 08m
1 stop
$601Multiple Airlines
Fri, May 22 - Tue, Jun 30
Multiple Airlines Logo
10:10 am - 12:37 pm
POS
-
ORD
27h 27m
1 stop
Multiple Airlines Logo
1:50 pm - 6:55 pm
ORD
-
POS
28h 05m
2 stops
$607Multiple Airlines
Fri, May 22 - Tue, Jun 30
Multiple Airlines Logo
10:10 am - 12:37 pm
POS
-
ORD
27h 27m
1 stop
Multiple Airlines Logo
1:50 pm - 6:55 pm
ORD
-
POS
28h 05m
2 stops
$612Multiple Airlines
Booking Insights

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

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

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

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

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Port of Spain to Chicago O'Hare Intl Airport, 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 Port of Spain to Chicago O'Hare Intl Airport is December, where tickets cost $375 (return) on average. On the other hand, the most expensive months are April and August, where the average cost of round-trip tickets is $1,481 and $829 respectively.

Good to know

Low seasonMarch
Cheapest flight$253
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 4% increase in price.
Flight from Port of Spain to Chicago

When to book flights from Port of Spain to Chicago

Are your dates flexible? Find out the best times to travel from Port of Spain to Chicago 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 Port of Spain to Chicago flights

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

    In the last 3 days, the lowest price for a flight from Port of Spain to Chicago O'Hare Intl Airport was $253 for a one-way ticket and $528 for a round-trip.

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

    A passport is required to fly from Port of Spain to Chicago.

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

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

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

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

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

    The two airlines most popular with KAYAK users for flights from Port of Spain to Chicago are Copa Airlines and United Airlines. With an average price for the route of $563 and an overall rating of 7.5, Copa Airlines is the most popular choice. United Airlines is also a great choice for the route, with an average price of $720 and an overall rating of 7.4.

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

    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 Port of Spain to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Port of Spain 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 Port of Spain to Chicago?

    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 Chicago with an airline and back to Port of Spain with another airline. Booking your flights between Port of Spain and ORD 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 Port of Spain to Chicago?

    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 Chicago from Port of Spain up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • Which airlines provide the cheapest flights from Port of Spain to Chicago?

    In the past 3 days, the cheapest round-trip tickets from Port of Spain to Chicago were found on Air Canada ($646) and Copa Airlines ($678).

Reviews of the top 4 airlines serving from Port of Spain to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Port of Spain to Chicago. 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 Port of Spain to Chicago? 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.
7.5
Copa AirlinesOverall score based on 1578 reviews
6.8Entertainment
6.8Food
7.4Comfort
8.1Crew
7.8Boarding
Airline reviews

I was flying business class, and the French fellow passengers were super noisy. It was not a comfortable flight. And the crew was not helpful.

2.0 MediocreFiruz, Apr 2026
MEX - PTY
Read more Copa Airlines reviews

I was flying business class, and the French fellow passengers were super noisy. It was not a comfortable flight. And the crew was not helpful.

Entire experience from check in to landing was amazing the flight crew was excellent and friendly. Seats were comfortable.

Do not book it’s a scam! They stole $1200 from me

Flight got delayed; had to go through security three times.

A lot things happened in this trip.The fly should be less stress.

There should be a warning regarding the quality of the aircraft on the website as we reserve the tickets. There was no TV or any type of screen onboard. The wifi they offer is good for nothing. Traveling 9 hours straight with kids and no type of entetainment was horrible. I wish I had been informed prior so I could buy a ticket with another airline. The food was a joke too. A very tiny portion per passenger. They also charged $100 per checked bag. With United I used to pay $60. So, fair to say that I wont be flying Copa anymore. Their aircraft was super old, outdated, no entertainment, with nearly no onboard food.

The flight was good overall. Everything went smoothly, although the landing was a bit rough. Still, it was a pleasant experience

Some of the Air hostesses are not that friendly. Need improvement

As always, Copa Airlines is great to fly on. The flights are always on time, the staff are pleasant and helpful and it's always a wonderful flying experience.

We had a great flight just wished they had a tv so we can see a movie that would of made my trip excellent.

Flight crew was super friendly and helpful. Food was frequent and honestly pretty good. Plenty of on-board entertainment. Economy seats are super cramped for such a long flight, but the crew allowed people to get up and stretch, and kids could wander with their parents, so we all made it work. Overall a very good experience.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Starlink is great Crew was polite Business class didn’t get a welcome drink just water and snacks were ok

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

very average service no complimentary alcoholics drinks unlike other airlines such as Porter airlines No decent seats available during check-in time the day before

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Very comfortable flight, snacks and drinks were good, good communication from crew. Could have used a little more information on timing of boarding for group 5

It was good, the staff was great, and the food, was as usual, tea and biscuit. Bathroom was clean, and the plane was clean as well.

Very good I can’t complain one bit. Thank you American Airlines for making my flight enjoyable and safe!

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

I'm not sure American is capable of on-time arrivals and departures. When you land at ORD, you almost always get held on the tarmac because your gate is still occupied. I may have missed my connection, but that ended up up being significantly delayed as well. Once again, I finally got home well after midnight.

Didn't make it back on American Airlines due to a maintenance issue. The communication and updates were terrible. I ended up returning on Aero Mexico which had a much nicer aircraft with a large entertainment screen with movies and shows AND they had a nice inflight meal. That was a treat after being delayed 26 hours! I think some additional flight miles, or something should be offered for that long of a delay ---it was not pleasant at all---very physical and emotional experience.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

The staff are very, very professional. It's what flying should feel like.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

Delays with no explanation. It could have been handled better.

Flight itself was not bad at all. However: my checked bag (checked in Calgary) did not make it onto this flight as I found out after I landed at EWR. I still don't have it but it appears that it is on its way to me.

Flight and attendance were very good we had 2 hour delay that took the shine of it

After 3 hours of delays, they ended up cancelling my flight. And although I could purchase one-way tickets to get to my destination, they would not offer me these flights as compensation for the cancelled flight, and I didn't end up making it home until 13 hours after I was originally supposed to arrive. It made for an extremely strenuous end to an otherwise good trip.

Be careful about the bad policy and when purchasing seats

Very disappointed with premier lounge. Food selection very poor, both coffee machines out of order. For the price you charge for an upgrade, the seats don’t fully recline, movie selection is old. Not very good value. Asian airlines are light years ahead at a more affordable price.

The seat design in the premium economy section leaves virtually no room under the seat to store a bag or purse. Other than that, it was a great flight. Arrived early.

The flight was delayed, but not for weather. We landed over 3hrs later than planned.

The stag were helpful, kind and liked the passengers. The plane was pristinely clean! Great flight!

My flight was delayed more than once, but Air Canada updated us regularly. Friends on other airlines had much worse experiences.

My ticket did not exist when I got to the airport. I had to book another flight and was still charged by Kayak

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

Information on your arrival and departure airports