POS - ORD

$308 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 5/27. 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

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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Cheap Flights from Port of Spain to Chicago

 
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.

Recent round-trip flight deals from Port of Spain to Chicago

KAYAK's recommended round-trip deals from the most popular airlines that fly from Port of Spain to Chicago.
Discover the best prices for you by selecting your travel dates on KAYAK.
 Logo
2:25 am - 7:27 amPOS-ORD
30h 02m3 stops
 Logo
8:25 pm - 1:25 amORD-POS
28h 00m1 stop
Fri, May 30 - Thu, Jun 5
Air Canada Logo
2:25 am - 6:53 pmPOS-ORD
17h 28m2 stops
Air Canada Logo
6:30 pm - 1:25 amORD-POS
29h 55m1 stop
$544Air Canada
Find Deal
Fri, May 30 - Thu, Jun 5
Air Canada Logo
2:25 am - 3:04 pmPOS-ORD
13h 39m1 stop
Air Canada Logo
10:40 am - 1:25 amORD-POS
13h 45m2 stops
$550Air Canada
Find Deal
Sun, Jul 6 - Fri, Jul 18
Copa Airlines Logo
3:48 am - 1:42 pmPOS-ORD
10h 54m1 stop
Copa Airlines Logo
3:07 pm - 1:48 amORD-POS
9h 41m1 stop
$551Copa Airlines
Find Deal
Tue, Jul 1 - Wed, Aug 13
Air Canada Logo
2:25 am - 6:53 pmPOS-ORD
17h 28m2 stops
Air Canada Logo
8:40 am - 1:25 amORD-POS
15h 45m2 stops
$556Air Canada
Find Deal
Sun, Jul 6 - Fri, Jul 18
United Airlines Logo
12:30 am - 11:12 pmPOS-ORD
23h 42m1 stop
United Airlines Logo
6:00 am - 11:23 pmORD-POS
16h 23m1 stop
$561United Airlines
Find Deal
Fri, Jun 13 - Sat, Jun 21
United Airlines Logo
12:30 am - 9:55 amPOS-ORD
10h 25m1 stop
United Airlines Logo
12:45 pm - 11:23 pmORD-POS
9h 38m1 stop
$563United Airlines
Find Deal
Wed, Jun 18 - Thu, Jul 31
American Airlines Logo
3:15 pm - 11:51 pmPOS-ORD
9h 36m1 stop
American Airlines Logo
6:55 am - 9:36 pmORD-POS
13h 41m2 stops
$567American Airlines
Find Deal
Wed, Jul 2 - Wed, Aug 13
American Airlines Logo
3:05 pm - 9:00 amPOS-ORD
18h 55m1 stop
American Airlines Logo
7:16 pm - 2:05 pmORD-POS
17h 49m1 stop
$608American Airlines
Find Deal
Tue, May 20 - Tue, Jun 3
JetBlue Logo
8:50 am - 11:25 pmPOS-ORD
15h 35m1 stop
JetBlue Logo
6:15 am - 6:04 pmORD-POS
10h 49m1 stop
$692JetBlue
Find Deal
Sat, Jun 14 - Sat, Jun 21
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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 February, where tickets cost $561 (return) on average. On the other hand, the most expensive months are April and July, where the average cost of round-trip tickets is $1,481 and $850 respectively.

Good to know

Low seasonFebruary
High seasonJuly
Cheapest flight$308
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly with an average 20% 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 $308 for a one-way ticket and $539 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, United Airlines or American Airlines?

    The two airlines most popular with KAYAK users for flights from Port of Spain to Chicago are United Airlines and American Airlines. With an average price for the route of $613 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 $663 and an overall rating of 7.2.

  • 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.

Top airlines flying 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.
7.4
United AirlinesOverall score based on 8696 reviews
7.1Entertainment
7.3Comfort
7.7Boarding
8.1Crew
6.6Food
Airline reviews

So far so good but food and entertainment are not available for this flight

8.0 ExcellentAnonymous, Apr 2025YUL - ORD
Read more United Airlines reviews

So far so good but food and entertainment are not available for this flight

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

It was my first time with United Airlines and I would say it was very good experience and best of all the flights were on time. Will definitely fly with United Airlines next time.

Very modern plane. Good seat spacing. Meals were good. Screens had tons of movies and worked

There's just no way to sit fully upright and comfortably in these seats. There needs to be 2 more inches of room, and that's not something that only one person on the flight needs - the whole flight needs 2 more inches of room. If that means you sell 6 less seats, so be it. It's too close for anyone. Forcing people to pay for "premium" economy just to get "barely enough space to breathe" isn't really an answer to that.

The crew were very nice. The Chocolate is good and v there’s no entertainment. Thanks

The crew were very nice. I would have appreciated a pillow for comfort. I had a special meal that was sloppy, but the salad was great. Thanks

The plane was in Moline all night. Consequently, we assumed an on time departure at 8:15am. Unfortunately, and as is the normal case with United in Moline, we departed 2.5 hours late. When the crew came, it was discovered that there was very little heat in the plane. Seems this should have been checked hours before the crew arrived. Then when we boarded and the plane was to be de-iced, the United de-icing truck was not working! We awaited the American Airlines truck. All of this caused us to miss our connection in Chicago. My suggestion is never take United Airlines flight from Moline. We have been disappointed 80% of the time and have vowed to not take United again from Moline.

Flight was delayed two hours. No snacks and no tv screens. My bag got stuck in Chicago

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

Seating was horrible. Small seats. Access to flight information and extras very iser unfriendly. Kept losing internet after paying for it. Staff in madison was as unprofessional and unhelpful.

Delayed due to no crew. On a major holiday travel day.

Other than being delayed 5.5 hours and having to get a hotel because I missed my connecting flight, it was an okay flight. No in-flight Wi-Fi or entertainment.

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

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