POS - ORD

$417 Find Cheap Flights from Port of Spain to Chicago

This is the cheapest round-trip 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 4/10. 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 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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Everything you should know

Cheapest round-trip
$417
Typical prices: $1,335-$1,610
Copa Airlines
Fri 4/10Mon 4/13
POS - ORD • 1 stop
Top airlines
Cheapest • from $417 (round-trip)
Best reviews • 7.5 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Port of Spain and Chicago. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $582 (round-trip)
Shortest trip • 10h 40m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 44% 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 Chicago!
Flight Deals
Booking Insights
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

Fri, Apr 10 - Mon, Apr 13
Copa Airlines Logo
2:17 pm - 1:13 am
POS
-
ORD
11h 56m
1 stop
Copa Airlines Logo
8:06 am - 1:40 am
ORD
-
POS
16h 34m
1 stop
$417Copa Airlines
Thu, Apr 16 - Sun, Apr 26
Air Canada Logo
1:20 am - 1:05 pm
POS
-
ORD
12h 45m
1 stop
Air Canada Logo
8:40 am - 12:20 am
ORD
-
POS
14h 40m
2 stops
$423Air Canada
Thu, Apr 16 - Sun, Apr 26
Air Canada Logo
1:20 am - 1:05 pm
POS
-
ORD
12h 45m
1 stop
Air Canada Logo
9:05 am - 12:20 am
ORD
-
POS
14h 15m
1 stop
$425Air Canada
Thu, Apr 16 - Sun, Apr 26
Air Canada Logo
1:20 am - 6:58 pm
POS
-
ORD
18h 38m
2 stops
Air Canada Logo
8:40 am - 12:20 am
ORD
-
POS
14h 40m
2 stops
$429Air Canada
Thu, Apr 9 - Mon, Apr 13
Air Canada Logo
1:20 am - 2:55 pm
POS
-
ORD
14h 35m
2 stops
Air Canada Logo
9:20 pm - 12:20 am
ORD
-
POS
26h 00m
1 stop
$434Air Canada
Thu, Apr 9 - Sun, Apr 12
Air Canada Logo
1:20 am - 6:58 pm
POS
-
ORD
18h 38m
2 stops
Air Canada Logo
2:00 pm - 12:20 am
ORD
-
POS
9h 20m
1 stop
$443Air Canada
Thu, Apr 9 - Sun, Apr 12
Air Canada Logo
1:20 am - 6:58 pm
POS
-
ORD
18h 38m
2 stops
Air Canada Logo
7:13 am - 12:20 am
ORD
-
POS
16h 07m
2 stops
$446Air Canada
Sat, Apr 25 - Sat, May 2
Copa Airlines Logo
2:17 pm - 1:13 am
POS
-
ORD
11h 56m
1 stop
Copa Airlines Logo
3:21 pm - 1:46 am
ORD
-
POS
9h 25m
1 stop
$455Copa Airlines
Sat, Apr 25 - Sat, May 2
Multiple Airlines Logo
9:10 am - 9:12 pm
POS
-
ORD
13h 02m
2 stops
Multiple Airlines Logo
1:27 pm - 8:00 pm
ORD
-
POS
29h 33m
1 stop
$488Multiple Airlines
Tue, May 5 - Sun, May 10
Copa Airlines Logo
3:49 am - 2:06 pm
POS
-
ORD
11h 17m
1 stop
Copa Airlines Logo
3:21 pm - 1:46 am
ORD
-
POS
9h 25m
1 stop
$492Copa Airlines
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.

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

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

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 December, where tickets cost $375 (return) on average. On the other hand, the most expensive months are April and May, where the average cost of round-trip tickets is $1,481 and $894 respectively.

Good to know

Low seasonMay
Cheapest flight$417
Best time to beat the crowds but there is an average 33% increase in price.
Most popular time to fly and prices are also 12% 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 $417 for a round-trip ticket.

  • 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?

    oneworld, and Star Alliance are the airline alliances operating flights between Port of Spain and Chicago, with oneworld 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 $563 and an overall rating of 7.5, Copa Airlines is the most popular choice. United Airlines is also a great choice for the route, with an average price of $792 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 4 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.
7.5
Copa AirlinesOverall score based on 1569 reviews
6.8Entertainment
7.4Comfort
7.8Boarding
8.1Crew
6.8Food
Airline reviews

Do not book it’s a scam! They stole $1200 from me

2.0 MediocreTalicia, Mar 2026
PTY - RDU
Read more Copa Airlines reviews

Do not book it’s a scam! They stole $1200 from me

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

A lot things happened in this trip.The fly should be less stress.

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.

The flight was good overall. Everything went smoothly, although the landing was a bit rough. Still, it was a pleasant experience

Some of the Air hostesses are not that friendly. Need improvement

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.

Would've been great if Lufthansa union cockpit pilots didn't strike for 2 days and caused a chaos to my returning plans to USA, and then after rebooking a flight 2 days later tge plane departed 35 min later. So I did not have a good experience.

They never clean the toilet, and the food is worse

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Chargers didn’t work, no entertainment and we had to wait for taxiing for easily 40 minutes after arriving early. Bags were late too!

No real complaints. The in flight food was much better than I expected. The in flight entertainment was excellent.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

Horrible Flight significantly delayed. Not due to united issue. But trying to rebook connection flight and get information about overnight accommodation was difficult. Agent did not seem to care or have any interest to help.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

This Japanese airline provides great service and very helpful in assisting their passengers.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

There was no inflight service. Once we landed we were delayed to find a gate for an hour and a half which was 1/2 the total time in the air.

I understand that there is a catering issue - water should be the minimum stock. During the flight, not once that the attendants came through with water. The conversations in the kitchen were very loud and they were swearing. I do not expect any white glove service, at the minimum, we should be cordial. It was almost an inconveniece that we were on the flight. And it made us feel if you even dare question us, we'll make you deplane.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

It was good experience this time. The flight was on time.

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

Overall, my last three trips on American Airlines have all been either delayed or "rescheduled" due to mechanical issues. At least on delay caused me to miss two possible connecting flights each later than the first. My last option for my last connection required the assistance of the onsite service desk (O'Hare Airport). The wait time for the service desk was such that it jeopardized getting booked on the last connecting flight available for the night. Suffice it to say, my latest experiences with American Airlines have caused me extensive loss of productive business and personal time and can therefore be classified as significantly less than satisfactory.

Waiting for gate in RDU for more than 20mins is crazy.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

Waited for oxygen tanks for 30 minutes after boarding was complete.

My ticket did not exist when I got to the airport. I had to book another flight and was still charged by Kayak

Got denied my flight was told on Google that Air Canada was supposed to book me a flight back home because I never was able to go to my destination. They did not help me whatsoever. I had to book a whole new flight for that reason I would write this is zero

The plane was delayed an hour. Heard from other passengers that the Vancouver connection to SFO was never on-time.

My experience was good with United too But only not so good thing was that at Calgary airport I was not given lounge access despite of flying business. Aspire lounge denied it to me, which was unfair I feel

We left over 2 hours late and they didn't even give us a complimentary snack, when getting to the desk I asked if I could be put in a row with only 1 other person or an empt y one I was told the flight was full when the last two rows were empty. All around over it

they were super helpful. Agents at the desk got me on an earlier flight and I was able to get home several hours earlier.

This is a great non-stop YVR-MIA. Very comfortable plane, and no transfer through a city that gets major winter weather!

Terrible…. Reported missing luggage’s with injectable meds that needed refrigeration. Yet, delivery could not be expedited. Luggage’s were delivered 5 days after arrival. The meds were useless as ice pack had melted. So disappointed!!!

Air Canada’s problems are not staff related by and large, no. The problem is tiny jets between the U.S. and Canada - yes, believe it or not they are still “international” (just ask our own Mango Maniac in power in the U.S.). The little aisle is compounded by a design flaw of a “dog leg” starting at seat 12. Woe be unto you if you sit here as passengers and attendants do not have sufficient room to not hit you in the face with backpacks. One thing I will say very positively about Air Canada is you still provide pillows and blankets on transcontinental flights to all, not just the elites. Your tiny improperly designed jets are also a problem flying city to city within Canada also. One can only say you remind us of a “Jet Blue” or “Spirit” experience. Also your luggage space is downright Byzantine! We will endeavor to avoid you and use other U.S. carriers, albeit charging more.

Terrible canceled flight and lost my luggage. Flew me to Halifax. Tgat flight was delayed, had to spend night in airport chair.

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

Information on your arrival and departure airports