POS - ORD

$322 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 12/25. 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 24% 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
$440
Overall average: $579
Air Canada
Tue 1/20Fri 1/23
POS - ORD • 1 stop
Cheapest one-way
$322
Air Canada
Thu 12/25
POS - ORD • 1 stop
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

Tue, Jan 20 - Fri, Jan 23
Air Canada Logo
2:20 am - 3:10 pm
POS
-
ORD
14h 50m1 stop
Air Canada Logo
10:00 am - 1:20 am
ORD
-
POS
13h 20m1 stop
$440Air Canada
Fri, Jan 23 - Fri, Jan 30
Multiple Airlines Logo
9:10 am - 6:16 pm
POS
-
ORD
11h 06m1 stop
Multiple Airlines Logo
5:15 am - 8:00 pm
ORD
-
POS
12h 45m1 stop
$451Multiple Airlines
Fri, Jan 23 - Fri, Jan 30
Multiple Airlines Logo
9:10 am - 6:16 pm
POS
-
ORD
11h 06m1 stop
Multiple Airlines Logo
5:15 am - 8:00 pm
ORD
-
POS
12h 45m1 stop
$456Multiple Airlines
Tue, Jan 20 - Fri, Jan 23
Air Canada Logo
2:20 am - 6:55 pm
POS
-
ORD
18h 35m2 stops
Air Canada Logo
10:00 am - 1:20 am
ORD
-
POS
13h 20m1 stop
$461Air Canada
Thu, Jan 22 - Fri, Jan 30
Air Canada Logo
2:20 am - 6:55 pm
POS
-
ORD
18h 35m2 stops
Air Canada Logo
2:00 pm - 1:20 am
ORD
-
POS
9h 20m1 stop
$463Air Canada
Tue, Jan 20 - Fri, Jan 23
Air Canada Logo
2:20 am - 6:55 pm
POS
-
ORD
18h 35m2 stops
Air Canada Logo
10:35 am - 1:20 am
ORD
-
POS
12h 45m2 stops
$464Air Canada
Thu, Jan 22 - Fri, Jan 30
Air Canada Logo
2:20 am - 6:55 pm
POS
-
ORD
18h 35m2 stops
Air Canada Logo
7:15 am - 1:20 am
ORD
-
POS
16h 05m2 stops
$466Air Canada
Thu, Jan 22 - Fri, Jan 30
Air Canada Logo
2:20 am - 6:55 pm
POS
-
ORD
18h 35m2 stops
Air Canada Logo
2:00 pm - 1:20 am
ORD
-
POS
9h 20m1 stop
$483Air Canada
Thu, Jan 8 - Thu, Jan 15
Multiple Airlines Logo
10:10 am - 7:38 pm
POS
-
ORD
11h 28m1 stop
Multiple Airlines Logo
7:20 am - 8:00 pm
ORD
-
POS
10h 40m1 stop
$486Multiple Airlines
Fri, Dec 26 - Wed, Jan 14
Air Canada Logo
2:15 am - 1:01 pm
POS
-
ORD
12h 46m1 stop
Air Canada Logo
8:45 pm - 1:20 am
ORD
-
POS
26h 35m1 stop
$519Air Canada
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.

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

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

If your flying dates are flexible, you should consider flying to Chicago on a Thursday, as we generally find the cheapest rates on that day for this route. On the other hand, Wednesday is the most expensive day to fly from Port of Spain to Chicago. For your return ticket, we recommend flying on a Sunday and avoiding Mondays for the best deals.

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$322
Best time to beat the crowds with an average 13% 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 $322 for a one-way ticket and $440 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
7.8Boarding
7.4Comfort
6.8Entertainment
6.9Food
8.1Crew
Airline reviews

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

8.0 ExcellentAnonymous, Oct 2025
PTY - IAD
Read more Copa Airlines reviews

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

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.

We paid extra with copa for seats near one another The plane was changed and we lost our seats We were all Separated. We have not received a refund for our seats despite emailing and calling.

Tell people to remain in their seats during the meal/beverage distribution. Enforce boarding by group numbers. No one was checking. Tell people to turn their electronics speakers off. Bigger cups for drinks.

Placed us in the last rear row of the plane so could not recline seats because of the rear wall, and also made it more of a tight space when the passenger in front reclined their seat. While understand seat assignments, every passenger should be afforded a reclining seat. The odor control scent from the restrooms was overwhelming strong. My wife and I could not deal with it, and she suffered a terrible headache as a result. I kept getting hit by the crew since I was on the ilse seat. No apologies, nothing. They made me feel like I was supposed to take the beating for a 3 hr flight.

We were in transit from Lima (flight at 1.10am) and we were in stand by in our flight from Panama to Washington. We wait from 4.30 am to 18.30pm in the Airport. The company give us 2 x 15 dollars for eat during the day and a personnal travel voucher of 400 dollars each. Do they buy food one time something in the Airport ??? And one of us live in France so the voucher is not usable. More than 24 hours travel !! And our place were near the toilets, with 8 children around us. The boy behind my seat stamped his feet on my back all the flight. Really Wonder full ! So we are totally unhappy with our travel. Thanks Copa Airlines....

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Very bad! They kept delaying my flight and wouldn’t do anything about it

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

United has come a long way, it’s been a fantastic experience traveling with them.

This flight leg was fantastic - super comfortable and a great selection of things to watch on the TV. Staff were excellent, really above and beyond.

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Excellent all round, first time flying United. App is very helpful.

Efficient all round, very good crew. Short flight so the food, of course, was just snacks

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.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

Premium economy seat was decent. As always poor headphones, poor food and beverage, crew is not overly friendly

Excellent - explanations were clear staff was nice and flight was comfortable

Lost bag and 2 days no word leaving for cruise no clothes or stuff

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

Information on your arrival and departure airports