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ORD - POS

$398 Find cheap flights from Chicago to Port of Spain

This is the cheapest round-trip 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 6/5. 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
0 bags
Thu 6/6
Thu 6/13

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
In the last 7 days travelers have searched 43,707,506 times on KAYAK, and here is why:

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Cheap flight deals from Chicago to Port of Spain (ORD-POS)

Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Port of Spain 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 and deals for you by selecting your travel dates.
Choose your dates
5:05 am - 1:42 amORD-POS
19h 37m2 stops
2:20 pm - 9:04 amPOS-ORD
19h 44m2 stops
Wed, Jun 5 - Wed, Jun 12
9:15 pm - 6:55 pmORD-POS
20h 40m1 stop
4:05 am - 5:40 pmPOS-ORD
38h 35m2 stops
Tue, May 14 - Tue, May 21
7:40 am - 1:42 amORD-POS
17h 02m3 stops
2:20 pm - 9:04 amPOS-ORD
19h 44m2 stops
Wed, Jun 5 - Wed, Jun 12
8:53 am - 11:23 pmORD-POS
13h 30m1 stop
12:30 am - 10:53 amPOS-ORD
11h 23m1 stop
$427United Airlines
Find Deal
Wed, Jun 5 - Tue, Jun 11
6:54 pm - 2:20 pmORD-POS
18h 26m1 stop
3:20 pm - 9:00 amPOS-ORD
18h 40m1 stop
$450American Airlines
Find Deal
Wed, Jun 5 - Wed, Jun 12
7:10 pm - 2:14 pmORD-POS
18h 04m1 stop
3:18 pm - 9:02 amPOS-ORD
18h 44m1 stop
$517American Airlines
Find Deal
Mon, Jul 8 - Tue, Oct 8
8:45 am - 11:23 pmORD-POS
13h 38m1 stop
12:30 am - 7:48 amPOS-ORD
32h 18m1 stop
$544United Airlines
Find Deal
Thu, Jun 27 - Sun, Jul 7
3:10 pm - 1:42 amORD-POS
9h 32m1 stop
4:09 am - 1:18 pmPOS-ORD
10h 09m1 stop
$555Copa Airlines
Find Deal
Thu, Jul 11 - Mon, Jul 15
3:10 pm - 1:42 amORD-POS
9h 32m1 stop
4:09 am - 1:18 pmPOS-ORD
10h 09m1 stop
$650Copa Airlines
Find Deal
Thu, Jun 27 - Mon, Jul 8
5:15 pm - 3:55 amORD-POS
9h 40m1 stop
5:10 am - 4:30 pmPOS-ORD
12h 20m1 stop
$768JetBlue
Find Deal
Tue, Jul 9 - Fri, Jul 12

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 flights from Chicago O'Hare Intl Airport to Port of Spain clicked on KAYAK for each day over the last 12 months.
Your flight ticket price will generally be cheaper if you fly to Port of Spain on a Sunday and more expensive on a Saturday. On your return trip to Chicago, you should consider flying back on a Wednesday, and avoid Mondays for better deals.

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 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 on average. On the other hand, the most expensive months are November and December, where the average cost of tickets is $1,024 and $942 respectively.

How far in advance should I book a flight from Chicago O'Hare Intl Airport to Port of Spain?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights from Chicago O'Hare Intl Airport to Port of Spain, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price on the flight from Chicago O'Hare Intl Airport to Port of Spain, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 85 days before departure.

Which airlines provide the cheapest flights from Chicago to Port of Spain?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
The best deals for a one-way ticket found by KAYAK users over the last 3 days were on American Airlines ($656) and United Airlines ($657). The cheapest round-trip tickets were found on United Airlines ($427) and American Airlines ($450).

Good to know

Low season

January

High season

March

Cheapest flight

$398
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly with an average 19% 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 $656 for a one-way ticket and $398 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 $532 and an overall rating of 7.8, Copa Airlines is the most popular choice. United Airlines is also a great choice for the route, with an average price of $664 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.
7.8
Copa AirlinesOverall score based on 2781 reviews
7.3Food
8.3Crew
7.2Entertainment
7.7Comfort
8.1Boarding
Airline reviews

Copa performed as expected for the amount of money I was willing to spend for the flight; it wasn’t exceptional but it was not bad in any way either. The crew was good; friendly and straightforward. The food was airplane food, so no expectations there and the entertainment was lacking but that was my fault for owning an IPhone with a charging port that’s not compatible with the rest of the world. I’d fly Copa again.

8.0 ExcellentAntonio, Mar 2024LAX - PTY
Read more about Copa Airlines reviews

Copa performed as expected for the amount of money I was willing to spend for the flight; it wasn’t exceptional but it was not bad in any way either. The crew was good; friendly and straightforward. The food was airplane food, so no expectations there and the entertainment was lacking but that was my fault for owning an IPhone with a charging port that’s not compatible with the rest of the world. I’d fly Copa again.

Left my bags in origin city on a business class ticket , spent about 2-3 days in the same clothes plus the flight .

the planes are not modern there are no phone chargers

As usual, the flight with normal legroom was not very comfortable, but the second flight was much better because we had paid for extra legroom. It was very nice to check our bags without an extra fee.

LOCKED MY BAG WITHOUT CONSENT. Had to have my zippers cut upon arrival in Costa Rica.

Pros: "The seats in economy were confortable. The best thing was Copa gave us seats in the second line and my family traveled together."
Cons: "Coffe service could better the experience"
Pros: "The crew was very interested on help and attentive with the passengers. But the seat wasn't comfortable. The design of the cushion is not the best to be seating"
Pros: "You were on time, that is the most important thing in a fly"
Cons: "You could improve your entertainment, you are not a cheap company"
Pros: "That there was seltzer"
Cons: "The management of preparing the flight and plane so that it was ready for the trip!!"
Pros: "Copa was convenient and easy. Very easy boarding process and I appreciated the day flight."
Cons: "This is a business class that is equivalent to a US carrier domestic first class. Good seats, not lay flat but wide on my 737-800. The food and service emulated say American Airlines Domestic 1C as well. Everything was just good enough, and much cheaper that international business on the majors."

Great! The plane was decently sized and comfortable. The staff was nice and there was great in flight entertainment

Last minute gate change nearly caused us to miss our flight. Change was not announced or displayed in the main board at the old gate. Terrible communication. When we landed we had to wait 20 minutes because there was another plane at the assigned gate. Not the crew’s fault, but adding 20 minutes to a 45 minute flight sucked.

Nothing beats ANA customer service on my opinion. Maybe because of their Japanese culture (and food). Arigatō

delay several times and wait extra long to board. no entertainment service because there are problem for some rows. always encounter some delays for the last flight of the day.

Flight delayed for 2 hours due to a part. The plane sat waiting for boarding for a long time and during final preflight inspection the issue was found. Why not do the preflight inspection sooner if you know the plane is being used?

The flight experience was very good! Especially the United Club!

I was not able to buy food in the flight. They refer to include your Credit card in the APP, and if you are not from USA (i have a credit card form Canada) it is not possible

Aircraft has better leg room than any of United's larger planes. We had requested mobility assistance for this and related flights. United's response to all was superb.

The flight from Ottawa to Chicago took a lot longer due to DC in Ottawa. We got to Chicago and went to our gate to catch our flight. We only had nine minutes I found that very stressful.

Good boarding. Crew started quick with drinks and food. They came around several times for trash which I really liked. Other than turbulence due to storms in the area, flight was great.

It was spectacular. I had basic Economy and was given so much space and their seats lean back so far. Staff was superb, food was superb, everything was superb, Finnair is Fantastic.

Good flights. Departure and arrivals were on time. DFW was a little problematic in that the Skytrain without prior notice bypassed the Echo terminal so that delayed my arrival at my connecting flight.

Because I can’t stand very long in one place, I was allowed to reword.

We were delayed bc ground crew gave the flight crew the wrong paperwork. We taxiied to the runway then back to the gate to get the correct paperwork that no one bothered reviewing the first time we pushed back. Boarding was rude and stressful like it always is. Gate agents and flight attendants are all over 55 years of age, embittered by years of underpayment From AA leading to their passive agressive bitchiness for no reason.

Boarding time was easy & quick. Crew was excellent. In-flight entertainment was great/easy. Seats are too small and not enough room between rows: felt like a sardine/very cramped.

5 hour flight - full flight - not enough room to use my computer - slightly delayed - Admirals club was excellent quality food, drink made up for flight seating. No food offerred on flight, you ahd to prebook.

Excellent- plan was barely populated. I cannot remember a flight where I was able/encouraged to stretch out!

Great flight. Boarding was efficient and quick. On time departure and smooth flight. Flight arrived early at destination. Good experience.

Had technical issue which delayed the flight period. Flight crew knew there was 5 passengers that the connecting flight was within 15 minutes once at the gate. Rather than identify the 5 passengers to assure they got first. The flight attended mentioned it but didn't assist to assure passengers with connecting flights off first. This caused a hardship and our party of 3 missed the connecting flight.

I don't like that I have to pay if I want extra leg room. The seats are so expensive; I sit in normal seats and my legs and knees cramp the entire flight. I never feel comfortable on AA flights.

Book cheap flights from Chicago to Port of Spain

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Chicago to Port of Spain found on KAYAK in the last 72 hours.
5/17Fri
2 stopsAmerican Airlines
13h 04mORD-POS
$656
5/17Fri
1 stopUnited Airlines
14h 53mORD-POS
$657
5/17Fri
3 stops
28h 27mORD-POS
$3,736

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Last minute flights from Chicago to Port of Spain

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Chicago to Port of Spain that are departing in the next 10 days.
5/11Sat
multi-stop
24h 20mORD-POS
5/14Tue
multi-stop
29h 40mPOS-ORD
$556
5/11Sat
multi-stop
24h 20mORD-POS
5/15Wed
multi-stop
20h 24mPOS-ORD
$637
5/11Sat
multi-stop
23h 53mORD-POS
5/15Wed
multi-stop
15h 32mPOS-ORD
$677
5/11Sat
multi-stop
23h 47mORD-POS
5/15Wed
multi-stop
15h 32mPOS-ORD
$691
5/11Sat
multi-stop
23h 53mORD-POS
5/14Tue
multi-stop
20h 24mPOS-ORD
$693
5/9Thu
multi-stopUnited Airlines
13h 38mORD-POS
5/16Thu
multi-stopUnited Airlines
11h 18mPOS-ORD
$847
5/11Sat
multi-stopUnited Airlines
14h 53mORD-POS
5/13Mon
multi-stopUnited Airlines
10h 00mPOS-ORD
$937
5/11Sat
multi-stopAmerican Airlines
8h 10mORD-POS
5/15Wed
multi-stopAmerican Airlines
11h 42mPOS-ORD
$942
5/11Sat
multi-stopAmerican Airlines
15h 19mORD-POS
5/15Wed
multi-stopAmerican Airlines
13h 40mPOS-ORD
$943
5/11Sat
multi-stopAmerican Airlines
13h 34mORD-POS
5/15Wed
multi-stopAmerican Airlines
13h 40mPOS-ORD
$945

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Chicago - Port of Spain Flights

Departure:

Chicago (undefined)United States

Destination:

Port of Spain (POS)Trinidad and Tobago

Return flight deals:

Port of Spain - Chicago

Cabin classes: