ORD - POS

$253 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 8/18. 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 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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Everything you should know

Cheapest round-trip
$549
Typical prices: $739-$611
Multiple Airlines
Mon 7/13Fri 7/17
ORD - POS • 1 stop
Cheapest one-way
$253
Multiple Airlines
Tue 8/18
ORD - POS • 2 stops
Top airlines
Cheapest • from $602 (round-trip)
Best reviews • 7.6 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Chicago and Port of Spain. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $548 (round-trip)
Shortest trip • 9h 02m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 29% price drop
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 Port of Spain!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights 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 for you by selecting your travel dates on KAYAK.

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

Mon, Jul 13 - Fri, Jul 17
Multiple Airlines Logo
8:05 am - 8:00 pm
ORD
-
POS
10h 55m
1 stop
Multiple Airlines Logo
10:10 am - 12:15 pm
POS
-
ORD
27h 05m
1 stop
$549Multiple Airlines
Sat, Nov 14 - Sun, Nov 15
Multiple Airlines Logo
6:30 pm - 7:40 pm
ORD
-
POS
23h 10m
2 stops
Multiple Airlines Logo
2:20 am - 10:58 am
POS
-
ORD
10h 38m
1 stop
$556Multiple Airlines
Thu, Jul 9 - Fri, Jul 17
Multiple Airlines Logo
8:05 am - 8:00 pm
ORD
-
POS
10h 55m
1 stop
Multiple Airlines Logo
10:10 am - 12:15 pm
POS
-
ORD
27h 05m
1 stop
$563Multiple Airlines
Sun, Aug 2 - Fri, Aug 7
Air Canada Logo
9:50 am - 12:15 am
ORD
-
POS
13h 25m
1 stop
Air Canada Logo
1:25 am - 1:22 pm
POS
-
ORD
12h 57m
1 stop
$593Air Canada
Sun, Jul 12 - Fri, Jul 17
Multiple Airlines Logo
8:05 am - 8:00 pm
ORD
-
POS
10h 55m
1 stop
Multiple Airlines Logo
10:10 am - 12:15 pm
POS
-
ORD
27h 05m
1 stop
$598Multiple Airlines
Mon, Jul 13 - Sun, Jul 19
Air Canada Logo
8:45 am - 12:15 am
ORD
-
POS
14h 30m
2 stops
Air Canada Logo
1:25 am - 6:47 pm
POS
-
ORD
18h 22m
2 stops
$602Air Canada
Thu, Jul 2 - Sun, Jul 5
Air Canada Logo
3:45 pm - 12:15 am
ORD
-
POS
31h 30m
1 stop
Air Canada Logo
1:25 am - 1:22 pm
POS
-
ORD
12h 57m
1 stop
$603Air Canada
Thu, Jul 2 - Sun, Jul 5
Air Canada Logo
3:45 pm - 12:15 am
ORD
-
POS
31h 30m
1 stop
Air Canada Logo
1:25 am - 10:16 am
POS
-
ORD
33h 51m
2 stops
$607Air Canada
Fri, Jul 3 - Sun, Jul 19
Air Canada Logo
8:45 am - 12:15 am
ORD
-
POS
14h 30m
2 stops
Air Canada Logo
1:25 am - 6:44 pm
POS
-
ORD
18h 19m
2 stops
$610Air Canada
Tue, Jul 7 - Fri, Jul 17
Multiple Airlines Logo
9:57 pm - 6:55 pm
ORD
-
POS
43h 58m
2 stops
Multiple Airlines Logo
10:10 am - 12:15 pm
POS
-
ORD
27h 05m
1 stop
$611Multiple Airlines
Booking Insights

KAYAK's insights & trends for Chicago to Port of Spain flights

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.

How much is a round-trip flight from Chicago O'Hare Intl Airport to Port of Spain?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago O'Hare Intl Airport to Port of Spain departing in July.

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 November, where tickets cost $443 (return) on average. On the other hand, the most expensive months are December and February, where the average cost of round-trip tickets is $750 and $724 respectively.

Good to know

Low seasonJanuary
Cheapest flight$253
Best time to beat the crowds with an average 26% drop in price.
Most popular time to fly with an average 16% 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 5 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Port of Spain was $253 for a one-way ticket and $549 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 oneworld 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 $627 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 $649 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.

Reviews of the top 4 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 1569 reviews
7.4Comfort
7.8Boarding
6.9Food
6.8Entertainment
8.1Crew
Airline reviews

Same as the previous flight as far as comfort and food. Entertainment didn’t have a watchable screen so everything would need to be watched on your own device in which they didn’t have a charging port that accommodated my iPhone. Seats were very uncomfortable. Staff was very friendly.

6.0 GoodAnonymous, May 2026
PTY - LAX
Read more Copa Airlines reviews

Same as the previous flight as far as comfort and food. Entertainment didn’t have a watchable screen so everything would need to be watched on your own device in which they didn’t have a charging port that accommodated my iPhone. Seats were very uncomfortable. Staff was very friendly.

The food is terrible I ask for water never got transport my mother we’re late and my sister from Lima was the worst waiting to long for wheelchair

Flight got delayed; had to go through security three times.

Copa staff at PTY and one particular crew member were unhelpful & rude.

There should be a warning regarding the quality of the aircraft on the website as we reserve the tickets. There was no TV or any type of screen onboard. The wifi they offer is good for nothing. Traveling 9 hours straight with kids and no type of entetainment was horrible. I wish I had been informed prior so I could buy a ticket with another airline. The food was a joke too. A very tiny portion per passenger. They also charged $100 per checked bag. With United I used to pay $60. So, fair to say that I wont be flying Copa anymore. Their aircraft was super old, outdated, no entertainment, with nearly no onboard food.

I always enjoy flying Copa. There are very few airlines where I can enjoy a comfortable sleep in-flight. The snacks weren't the best, but they sufficed. The in-flight entertainment was fantastic, and I crossed another movie off my watch list.

Very strict carry on rules meant most of the plane had to gate check their luggage. As is often the case had things that were broken because of this, but I appreciated not being charged to gate check. Otherwise good flight and great crew once on the plane

I liked the meatloaf the chicken was awful but the plane was on time and got there and the staff was nice.

Boarding was quick & efficient; they gave boarding groups due priority; staff & air crew were very cordial and helpful, pleasant flight.

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.

Horrible! Several delays and then was cancelled! I spent over 24 hours in the airport and was unable to get a hotel or food voucher.

Smooth travel. Immediate update prior flight delay so I can arrange myself properly without too rush.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

I’ve got 31F seat and window seat . My 2 co passengers was AA crew members and they were very rude attitude and when I was going to use bathroom their gestures was very different and awkward and the guy beside me completely occupied the hand rest and I was really uncomfortable

It was so much better than expected, Ohare is not such a pleasant experience but American Airlines with the new, clean aeroplane and free Wi-Fi was outstanding and the crew so pleasant and helpful.

It wa sort of on time; the cab was left with some trash

My pillow had a shoe print on it, when I asked if I can have another pillow, I was told “I’m sorry but it is one pillow per guest, do YOU want to turn it inside out” to which I responded , no thanks I will go without. This is generally not ok, but For the price tag I paid flying business this is absolutely unacceptable. Hopefully American Airlines can update their accommodations to bedding that is not tossed on the ground and stepped on, or at least have a couple of extra pillows in hand, incase someone had decided to step on the pillows for what ever reason

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

Our flight was cancelled while we are on our way to the airport. So, no notice. We were rescheduled to another airline with a 2 hour later takeoff and so arrived at our destination on time. We pre-paid American Airlines $190 to upgrade our seats. No refund. So no use for AA or Kayak.

Terrible, horrible, disappointing- without telling us they changed planes and moved and separated our seats to opposite sides - said they changed seats putting us together - got to airport to find no, they did not - we sat opposing sides of plane - food overly salty to inedible, never saw stewardess but once - it was terrible

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Original flight was on time, then late, then changed gates...4 times. Once our newest plane came in, it was fine.

I almost missed my flight and they helped me out enormously

1didnt have wheel chair I ordered wheel chair in my ticket flight

Flight was overbooked and seats assigned to multiple passengers. Delay 1 hour to sort out.

Good but I don’t received my bags yet is been 5days still no update

It was pretty straight forward, no glitches or hidden costs

It was a short flight so, everything went smoothly and we got to where we needed to be safely.

Didn’t make it on the flight. Delayed then had to be rebooked, which in turn had me waiting at the airport for another 8 hours before next flight

No TV on the flight. The charging outlet was not working. No food, even a sandwich. The served orange was poor quality.

Selected seats 5 months prior to date. Had email confirmation and seats were not honoured. Family did not sit together

Loved and was pleasantly surprised by the food!! Request Lufthansa to help transiting passengers at Munich (confusion whether to go thru passport control or not).

The flight was comfortable and the staff were helpful and friendly. However, we did not know we were flying PAL until we arrived in Canada, so it was a bit disconcerting. In addition, which port we were leaving from was confusing.

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

Information on your arrival and departure airports