POS - ORD

$282 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 4/16. 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, 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$453
Typical prices: $525-$570
JetBlue
Mon 3/9Mon 3/16
POS - ORD • 1 stop
Cheapest one-way
$282
Multiple Airlines
Thu 4/16
POS - ORD • 1 stop
Top airlines
Air Canada
Cheapest • from $478 (round-trip)
Copa Airlines
Best reviews • 7.6 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
December
Cheapest • 42% price drop
July
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, Mar 9 - Mon, Mar 16
JetBlue Logo
8:05 am - 11:00 pm
POS
-
ORD
15h 55m
1 stop
JetBlue Logo
6:45 am - 1:36 pm
ORD
-
POS
29h 51m
1 stop
$453JetBlue
Mon, Mar 9 - Mon, Mar 16
Multiple Airlines Logo
9:10 am - 9:39 am
POS
-
ORD
25h 29m
1 stop
Multiple Airlines Logo
4:51 pm - 6:55 pm
ORD
-
POS
25h 04m
1 stop
$468Multiple Airlines
Tue, Mar 10 - Wed, Mar 18
Air Canada Logo
1:20 am - 1:01 pm
POS
-
ORD
12h 41m
1 stop
Air Canada Logo
8:40 pm - 12:20 am
ORD
-
POS
26h 40m
1 stop
$478Air Canada
Mon, Mar 9 - Mon, Mar 16
Multiple Airlines Logo
9:10 am - 9:39 am
POS
-
ORD
25h 29m
1 stop
Multiple Airlines Logo
6:16 pm - 6:55 pm
ORD
-
POS
47h 39m
2 stops
$489Multiple Airlines
Mon, Mar 9 - Mon, Mar 16
Multiple Airlines Logo
9:10 am - 9:39 am
POS
-
ORD
25h 29m
1 stop
Multiple Airlines Logo
6:16 pm - 6:55 pm
ORD
-
POS
47h 39m
2 stops
$497Multiple Airlines
Sun, Mar 8 - Mon, Mar 16
Air Canada Logo
1:20 am - 6:52 pm
POS
-
ORD
42h 32m
2 stops
Air Canada Logo
6:04 pm - 12:20 am
ORD
-
POS
29h 16m
2 stops
$532Air Canada
Sun, Mar 8 - Mon, Mar 16
Air Canada Logo
1:20 am - 8:10 pm
POS
-
ORD
19h 50m
2 stops
Air Canada Logo
6:04 pm - 12:20 am
ORD
-
POS
29h 16m
2 stops
$535Air Canada
Tue, May 5 - Sun, May 10
Copa Airlines Logo
3:49 am - 2:06 pm
POS
-
ORD
11h 17m
1 stop
Copa Airlines Logo
8:02 am - 1:46 am
ORD
-
POS
16h 44m
1 stop
$574Copa Airlines
Wed, Mar 11 - Wed, Mar 18
Multiple Airlines Logo
9:10 am - 4:55 pm
POS
-
ORD
32h 45m
3 stops
Multiple Airlines Logo
3:55 pm - 12:20 am
ORD
-
POS
31h 25m
1 stop
$581Multiple Airlines
Tue, Mar 10 - Wed, Mar 18
Multiple Airlines Logo
1:20 am - 9:10 am
POS
-
ORD
32h 50m
3 stops
Multiple Airlines Logo
6:01 pm - 12:20 am
ORD
-
POS
29h 19m
2 stops
$601Multiple 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 March.

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 $1,475 and $829 respectively.

Good to know

Low seasonMay
Cheapest flight$282
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly and prices are also 10% lower on average.
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 $282 for a one-way ticket and $468 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 $542 and an overall rating of 7.6, Copa Airlines is the most popular choice. United Airlines is also a great choice for the route, with an average price of $579 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.

Reviews of the top 3 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.
7.6
Copa AirlinesOverall score based on 1558 reviews
7.4Comfort
6.8Entertainment
7.8Boarding
8.1Crew
6.8Food
Airline reviews

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

6.0 GoodIrma, Jan 2026
PTY - MIA
Read more Copa Airlines reviews

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.

horrible service, food was an embarrassment, no charging for cellphones, stay away

the food served was an embarrassment. No connection for charging the cellphone... What a crappy airline.

Great experience with a crew always thinking in the passenger

Had to go through security at the gate again. Had to take off shoes and go through the whole thing again even though we have global entry. They asked us to check in items bought at duty free during our layover and since we checked our luggage at the original departure airport, they forced us to check in a small backpack. None of this ever happened with other airlines. In addition, no vegetarian food option and no snacks during a 7 hr flight. Luggage limits are unusually small. This is unacceptable. Will NEVER fly Copa again and will tell friends and family to avoid this airline.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

I so appreciate the crew members on each flight of United. They are outstanding.

Reliable, nice crew, I fly often on that flight and I like it all.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

The staff was nice, however boarding taking 2 hours. That’s insane. Overall very bad experience, a lot of turbulence and when landed in Chicago was horrible. I don’t think I’ll flight with UA again.

An international flight on an apron is pretty unusual in my 40 years of traveling. Departure delay. Luggage despite over an hour connection did not make it to the flight. Actually still in Germany. My luggage was not moved until I reached my final destination despite knowing it to be left in Germany upon my arrival in Chicago. The service left me a little off, both going and returning from Europe. Light on in the cabin even during a night flight and lots of traffic no matter what. Maybe passengers want more service? As a frequent traveler i just want to be able to sleep, the food will be better at the destination anyway. So since the cabin crew woke me up I asked for a cocktail, I did not get the best response although sitting in row 20 premium economy. I usually fly premium economy or business and my 2 flight to Europe in 2025 with United both had luggage delays and other minor issues. American flights to Australia, Canada and Europe went smoothly and Premium plus feels very much like business light. Is United Club becoming a waste and Silver/Gold levels another waste??

They did the one thing that really matters - got to Chicago early.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

Little warm on the plane and delayed for an hour

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

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.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Flight, food and crew were all good, friendly and very satisfactory.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

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

Information on your arrival and departure airports