ORD - POS

$241 Find Cheap Flights from Chicago to Port of Spain

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Port of Spain departing on 1/30. 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.
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Search hundreds of travel sites at once for deals on flights to Port of Spain

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Port of Spain, 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 Chicago to Port of Spain, as well as popular online travel agencies
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Cheap Flight Deals from O'Hare Intl to Piarco Intl (ORD-POS)

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

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Chicago to Port of Spain.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
8:46 pm - 1:15 pmORD-POS
14h 29m2 stops
6:01 pm - 10:36 amPOS-ORD
17h 35m1 stop
Fri, Mar 7 - Thu, Mar 13
6:45 pm - 2:00 pmORD-POS
18h 15m1 stop
3:15 pm - 9:07 amPOS-ORD
18h 52m1 stop
$528American Airlines
Find Deal
Thu, May 8 - Thu, May 15
6:45 pm - 2:00 pmORD-POS
18h 15m1 stop
3:15 pm - 7:15 amPOS-ORD
17h 00m2 stops
$533American Airlines
Find Deal
Thu, May 8 - Thu, May 15
6:55 am - 1:37 amORD-POS
16h 42m1 stop
3:39 am - 12:27 amPOS-ORD
21h 48m1 stop
$539Copa Airlines
Find Deal
Fri, Mar 7 - Wed, Mar 12
9:12 am - 4:41 pmORD-POS
30h 29m2 stops
6:01 pm - 8:55 amPOS-ORD
15h 54m2 stops
$613Frontier
Find Deal
Wed, Mar 19 - Thu, Mar 27
7:18 pm - 5:56 pmORD-POS
44h 38m2 stops
6:56 pm - 7:43 amPOS-ORD
38h 47m2 stops
$634Frontier
Find Deal
Fri, Feb 28 - Wed, Mar 5
12:55 pm - 1:05 amORD-POS
10h 10m1 stop
1:30 am - 10:09 amPOS-ORD
10h 39m1 stop
$711United Airlines
Find Deal
Wed, Feb 19 - Tue, Feb 25
2:20 pm - 1:05 amORD-POS
8h 45m1 stop
12:30 am - 10:09 amPOS-ORD
10h 39m1 stop
$768United Airlines
Find Deal
Fri, Mar 7 - Thu, Mar 13
8:25 pm - 1:35 amORD-POS
28h 10m1 stop
2:35 am - 7:38 amPOS-ORD
30h 03m2 stops
$799Air Canada
Find Deal
Sun, Jun 1 - Fri, Jun 6
8:25 pm - 1:35 amORD-POS
28h 10m1 stop
2:35 am - 10:54 amPOS-ORD
9h 19m1 stop
$811Air Canada
Find Deal
Sun, Jun 1 - Fri, Jun 6

Flights from Chicago to Port of Spain - Travel Insights & Trends

Get data-powered insights and trends into flights from Chicago to Port of Spain 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 Chicago to Port of Spain?

The average price of all round-trip flights from Chicago O'Hare Intl Airport to Port of Spain clicked on KAYAK for each day over the last 12 months.
For Chicago to Port of Spain, Sunday is the cheapest day to fly on average and Monday is the most expensive. Flying from Port of Spain back to Chicago, the best deals are generally found on Thursday, with Wednesday being the most expensive.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to Port of Spain, 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 Chicago O'Hare Intl Airport to Port of Spain is January, where tickets cost $493 (return) on average. On the other hand, the most expensive months are March and December, where the average cost of round-trip tickets is $776 and $759 respectively.

Good to know

Low season

December

High season

March

Cheapest flight

$241
Best time to beat the crowds but there is an average 20% increase in price.
Most popular time to fly with an average 22% increase in price.
Flight from Chicago to Port of Spain

When to book flights from Chicago to Port of Spain

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

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

    In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Port of Spain was $241 for a one-way ticket and $488 for a round-trip.

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

    Yes

  • Which airports will I be using when flying from Chicago to Port of Spain?

    When flying out of Chicago you will be using Chicago O'Hare Intl. You will be landing at Port of Spain, also known as Port of Spain Piarco Intl.

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

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

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

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

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

    The two airlines most popular with KAYAK users for flights from Chicago to Port of Spain are Copa Airlines and United Airlines. With an average price for the route of $535 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 $632 and an overall rating of 7.4.

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

    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 Chicago to Port of Spain.

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

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

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

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

See more FAQs

Top 3 airlines serving from Chicago to Port of Spain

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Port of Spain. 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 Chicago to Port of Spain? 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 1662 reviews
7.5Comfort
8.2Crew
7.0Food
6.9Entertainment
7.9Boarding
Airline reviews

Very good flight and crew Food was a surprise on a short flight

10.0 ExcellentAnonymous, Dec 2024LAX - PTY
Read more Copa Airlines reviews

Very good flight and crew Food was a surprise on a short flight

The plane doesn’t have screens but you can use your decide for entertainment. Pack a snack too since they don’t offer any, and the meal is pretty small and you will get hungry

Biggest issue was that they only had two restrooms in the back of the aircraft. Too many people for only two restrooms. The trash was overflowing and there was paper on the floor too. Long lines in the isle to use it. Food was also a bit meh. They don’t offer snacks with drinks, so you might want to buy a snack to hold you off on a longer trip, since the meals are very small.

It was first time fling in copa airline. In general I am satisfied except bag size. I got a email from copa with 17-10-6 for carry on bag. In airport the check in show 22-14-10 . However that mistake means $100,00 in over cost.

Boarding groups were called up in Spanish only. Luckily I know some of the language. They gave out grilled cheese sandwiches and a cup of fruit. I was very disappointed. I could only eat the cup of fruit because the only other option was vanilla pudding. The entertainment system and seating were great though.

Everything was smooth and crew was very polite and friendly.

Seemed roomier than most US domestic airlines and they served food.

The flight was 6 hours delayed due to equipment problems, I had to spend my night in the airport terminal in tight quarters. A bag of chips was all they offered, Then I missed my connecting flight and waited another 2 hours. All in all that trip took me almost one day.

I like that they served a mail, I’m not sure about the in-flight entertainment. I didn’t really check. staff helped me with my luggage. Smooth boarding smooth takeoff smooth flight

Just a minor inconvinient with weather delay! but not Copa's fault

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

The seats on this flight were almost roomy enough to be the basic amount needed for human existence.

Fight was delayed an hour due to operational issues ,then further delayed due to ground control for a total of about 1.30 hours. Salad was completely frozen and flatware was so cold you could barely handle it. Crew was friendly and professional and the flight was smooth. The aircraft was clean and well-serviced.

The flight attendants in First Class were mediocre at best. They did not take our tray away until we were about to land and only did so when I press the call button. The United person at the United Club was asked to get us our boarding pass since we missed the flight due in Chicago. She argued that we did not have seats on the flight given to us in Moline. Furthermore, she was adamant that we did not have a First Class ticket. After I spent much time with her trying to show we were correct, she reluctantly agreed. She was probably the most incompetent ticketing person I have ever met and I have traveled 3 million miles on United plus many additional miles with other carriers. United has definitely deteriorated in more than on way.

Short flight - no food understandable. Flight was delayed for over an hour. Overall, it was good.

We arrived early and finally made it to our gate almost an hour after.

Was a pain having to leave the plane and reboard but glad the plane was fixed

Plane was was better than th YVR to ORD flight but was a fraction of the distance. Fly your better planes on longer distance flights.

Nothing wrong with the flight itself. But due to 2+ hrs waiting in immigration and the additional security checkup in O’hare, I nearly missed the flight.

They need to improve their boarding process. Group 1 and/or paying first class passengers shouldn't be in the middle of boarding process

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The seat could not recline. This was not indicated as such when I paid for the seat. So itvwad not the most comfortable ride. At boarding, the staff could have more pleasant even though it may be an intense time.

The seat could not recline. This was not indicated as such when I paid for the seat. So itvwad not the most comfortable ride.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

WiFi was not working from pos to Mia…. As well as they rushed us to the gate as if the flight was already here and leaving shortly when the plane never even arrived and took off until the scheduled time so then why rush us to the gate and have us thinking we will miss our flight.

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

Information on your arrival and departure airports

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