POS - ORD

$314 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 12/24. 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

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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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, Oct 28 - Wed, Nov 5
Air Canada Logo
1:15 am - 8:00 pmPOS-ORD
43h 45m2 stops
Air Canada Logo
8:15 pm - 1:10 amORD-POS
26h 55m1 stop
$452Air Canada
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Wed, Oct 29 - Wed, Nov 5
Multiple Airlines Logo
2:27 pm - 9:22 amPOS-ORD
19h 55m2 stops
Multiple Airlines Logo
5:59 pm - 8:00 pmORD-POS
24h 01m1 stop
$463Multiple Airlines
Find Deal
Tue, Oct 28 - Wed, Nov 5
Air Canada Logo
1:15 am - 6:55 pmPOS-ORD
42h 40m2 stops
Air Canada Logo
6:05 pm - 1:10 amORD-POS
29h 05m2 stops
$471Air Canada
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Tue, Oct 28 - Wed, Nov 5
Multiple Airlines Logo
1:15 am - 8:00 pmPOS-ORD
43h 45m2 stops
Multiple Airlines Logo
7:35 am - 8:00 pmORD-POS
34h 25m3 stops
$540Multiple Airlines
Find Deal
Tue, Oct 28 - Wed, Nov 5
Copa Airlines Logo
3:51 am - 1:41 pmPOS-ORD
10h 50m1 stop
Copa Airlines Logo
6:56 am - 1:48 amORD-POS
16h 52m1 stop
$562Copa Airlines
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Thu, Feb 26 - Tue, Mar 3
United Airlines Logo
1:30 am - 11:09 amPOS-ORD
11h 39m1 stop
United Airlines Logo
7:35 am - 12:23 amORD-POS
14h 48m1 stop
$574United Airlines
Find Deal
Fri, Feb 27 - Tue, Mar 3
Copa Airlines Logo
2:33 pm - 12:31 pmPOS-ORD
23h 58m1 stop
Copa Airlines Logo
6:56 am - 1:15 pmORD-POS
28h 19m1 stop
$653Copa Airlines
Find Deal
Fri, Feb 27 - Tue, Mar 3
American Airlines Logo
4:40 pm - 12:24 pmPOS-ORD
21h 44m2 stops
American Airlines Logo
6:35 pm - 3:05 pmORD-POS
18h 30m2 stops
$721American Airlines
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Sun, Dec 14 - Sat, Dec 20
American Airlines Logo
4:33 pm - 12:37 amPOS-ORD
10h 04m1 stop
American Airlines Logo
5:00 am - 11:46 pmORD-POS
16h 46m1 stop
$1,128American Airlines
Find Deal
Sat, Dec 13 - Sat, Dec 20
United Airlines Logo
1:30 am - 7:46 pmPOS-ORD
20h 16m1 stop
United Airlines Logo
12:09 pm - 1:05 amORD-POS
10h 56m1 stop
$1,495United Airlines
Find Deal

Everything you should know

Top airlines
Air Canada
Cheapest • from $452 (round-trip)
Copa Airlines
Best reviews • 7.6 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
When to travel
June
Cheapest • 32% price drop
December
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$452
Overall average: $625
Air Canada
Tue 10/28Wed 11/5
POS - ORD • 2 stops
Cheapest one-way
$314
Typical prices: $394-444
United Airlines
Wed 12/24
POS - ORD • 1 stop
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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 June, where tickets cost $453 (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 seasonJune
Cheapest flight$314
Best time to beat the crowds with an average 33% drop in price.
Most popular time to fly and prices are also 17% 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 $314 for a one-way ticket and $452 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?

    Star Alliance, and oneworld are the airline alliances operating flights between Port of Spain and Chicago, with Star Alliance 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 $543 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 $581 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 1531 reviews
6.8Food
7.4Comfort
6.8Entertainment
7.8Boarding
8.1Crew
Airline reviews

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.

10.0 ExcellentNeil, Aug 2025PTY - BGI
Read more Copa Airlines reviews

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.

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.

It was ok. However, the food was quite poor since I don't eat pasta.

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.

Enforce the boarding process by group numbers. Tell people to stay seated during the meal/drink distribution. It took forever to get food and drinks because people would not stay out the isle and let the crew do their jobs. Everyone wanted to go to the bathroom forcing the crew to enter and leave the isle constantly so people can pass. Tell people to keep their electronics off speaker mode. No one wants to hear phone conversations and music playing.

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Inoperable monitor left no entert for 9 hours. Crew was not helpful Food was awful.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

All flight attendants could benefit by taking an international flight on Qantas Airline. Qantas attendants are much more hospitable in every way. Much superior than and attendants on any US airline.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The flight was on time and crew were nice, seats were tight and there was entertainment available

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

Worst flight ever. I was suppose to have a 3 1/2 hour layover in Chicago but got to the gate 4 minutes before boarding.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

They should have MSNBC available on board. A 4- hour flight should provide more than a cookie.

Was not able to watch most shows on the entertainment site. They would not load

On Wednesday, July 30 we were in mid flight from Manchester to Charlotte and we turned around because the right engine was malfunctioning. That was the last flight out of Manchester that night. I was rebooked for Thursday, which became a weather event Friday. There were no seats left on the flight from Manchester to Charlotte. Consequently I didn’t leave Manchester until Saturday morning and we flew to Chicago so to say the least my scheduled flight and return to Iowa was three days off and it messed with my business schedule. Consequently cash flow. I would like some sort of acknowledgment of this event.

Dreadful experience. Our flight was delayed more than 8 hours due to a maintenance issue and the assistance from rebooking was poor. I was travelling with a bad knee and needed assistance waited in one place more than 3 hours before someone came with a wheelchair. The woman next to me was a 91 year old great grandmother who had waited more than 4 hours. There were moments of support from the staff but it appeared as they were going against the direction of management. It was apathy, lack of ownership and dismissive responses with small moments of kindness and understanding typically from grey haired, female, veteran staff..

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

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