$295 Find Cheap Flights from Chicago to Trinidad and Tobago - Compare and Save

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Price, demand and travel trends for Chicago O'Hare Intl Airport to Trinidad and Tobago flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

What are the cheapest fares from Chicago O'Hare Intl Airport to Trinidad and Tobago right now?

The cheapest fare from Chicago O'Hare Intl Airport to Trinidad and Tobago in the last week was $638 round-trip, to Port of Spain Piarco Intl (POS).

Which airport in Trinidad and Tobago is the cheapest to fly to from Chicago O'Hare Intl Airport?

All flights from Chicago O'Hare Intl Airport to Trinidad and Tobago arrive at Port of Spain Piarco Intl (POS). On average, round-trip fares are around $660.

What’s the cheapest day to fly from Chicago O'Hare Intl Airport to Trinidad and Tobago?

Friday tends to be the cheapest day to fly from Chicago O'Hare Intl Airport to Trinidad and Tobago, while Monday is the most expensive. Fares run about 24% higher that day, based on the past 12 months of KAYAK data.

What's the cheapest time of day to fly from Chicago O'Hare Intl Airport to Trinidad and Tobago?

Data from the past 12 months shows it's cheapest to fly to Trinidad and Tobago during the evening with average prices of $607. The night is the most expensive time to fly, with average prices of $817.

Key details for Chicago O'Hare Intl Airport to Trinidad and Tobago flights

Low season

October

Cheapest flight

$308
Beat the crowds with an average 72% drop in travelers.
The most popular month to fly with an average 64% increase in travelers.
One-way flight from Chicago O'Hare Intl Airport to Port of Spain

Your Chicago O'Hare Intl Airport to Trinidad and Tobago flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • Is now a good time to book a flight from Chicago O'Hare Intl Airport to Trinidad and Tobago?

    Fares from Chicago O'Hare Intl Airport to Trinidad and Tobago are around their usual level right now. A round-trip under $595 is considered a good deal, so it's worth keeping an eye out, or setting a Price Alert to catch price changes.

  • How much should I budget for a flight from Chicago O'Hare Intl Airport to Trinidad and Tobago?

    Over the past 12 months, round-trip fares from Chicago O'Hare Intl Airport to Trinidad and Tobago have ranged from $595 to $779.

  • What are the main airports serving Trinidad and Tobago?

    Flights to Trinidad and Tobago all arrive at Port of Spain Piarco Intl (POS).

  • What airlines fly nonstop from Chicago O'Hare Intl Airport to Trinidad and Tobago?

    Based on the flight schedule for the next 3 months, no airline regularly operates nonstop flights from Chicago O'Hare Intl Airport to Trinidad and Tobago. One-stop options include:

    • American Airlines
    • United Airlines
    • Air Canada

  • Which cabin classes are available on flights from Chicago O'Hare Intl Airport to Trinidad and Tobago?

    On flights from Chicago O'Hare Intl Airport to Trinidad and Tobago you can only book Economy Class.

Your guide to booking Chicago O'Hare Intl Airport to Trinidad and Tobago flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your travel dates are flexible, book your trip for November when flights are typically cheapest and avoid September when prices are at their highest.
  • Flying on Friday is usually the cheapest. Flights on Monday cost about 24% more on average, so being flexible with your travel dates could help you save.
  • Start your trip in Port of Spain, which is the most popular destination in Trinidad and Tobago. From there, it's easy to continue on to other popular destinations such as Crown Point, Scarborough and Piarco.

Reviews of the top 3 airlines serving from Chicago to Trinidad and Tobago

 
Need help choosing which airline to fly with from Chicago to Trinidad and Tobago? 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 10356 reviews
7.7Boarding
8.1Crew
6.7Food
7.3Comfort
7.1Entertainment
Airline reviews

I especially enjoyed having a lightly packed flight which enabled me and my wife to occupy a three seat area with nobody in the middle seat.

10.0 ExcellentAJ, Oct 2026
Read more United Airlines reviews

I especially enjoyed having a lightly packed flight which enabled me and my wife to occupy a three seat area with nobody in the middle seat.

The seats are very small, that is all the staff did a good job.

It was great. The staff is always helpful and polite. The app is great and makes the whole trip and process so easy. They even offer a step to step guide to your correct terminal. And they keep all the information you'll need updated. Anything you can think of! Great experience.

Perfect. On time and the weather was perfect so we came in a few minutes early.

On time. Carry on and personal bag was accommodated on the plane. Entertainment was accessible without bringing own device. Whole can of juice was provided rather than a pour.

Price was crazy watch it if you Chan he your flight

On time, easy boarding. Anytime you sit in an economy seat, it’s uncomfortable. New plane and the bathrooms were in the galley at the back of the plane which seemed odd.

Terrible service - they don’t want to be there and bad food. Entertainment system in economy from the 2000s

No drink service but there was no N/A as an option to choose. Seats were extremely tight. I am under 5.5 and I bumped my knees have no idea how taller people could manage.

Flight delayed, last seat on the plane, no arrival Gate available due to the plane departing late

Same as my Tulsa to Chicago flight, this one was quick and professional.

Boarding was delayed 50 minutes. The flight going to Chicago was canceled, causing lots of problems and causing me to rebook and miss an event. I was traveling with a colleague, and he was unable to get on the same flight after 40 minutes on the phone, which meant I had to wait for him after my arrival. My flight down was delayed an hour before take off, had to sit on the plane, then 30 minutes after landing to get to a gate. No real food, only juice/ water offered for the 3.5 hours on the plane. Not a good experience.

The code sharing reservation with United was messed up requiring extra trip to airport to fix. Air Canada customer service 2.5 hours on hold and resolved nothing.

I'm 6'8" (2.03m) so more legroom would alwqys be appreciated, especially on long international flights. The food choices were underwhelming.

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

the check-in lady at ORD was extremely rude and unprofessional. very disappointed as it was supposed to be a celebration for my wife's birthday and it really put a damper on things. if i wanted to be treated like trash, i would have flown Economy! (as opposed to business class)

Short flight. Everything was fine except the flight was delayed twice for a total of an hour.

There labor disputes cancelled my flight less than 24 hours before my boarding time but there customer service/website was easy enough to navigate and they rebooked me for no upcharge.

Very bad, flight was cancelled due to strike and staff was unable to rebook us

Flight was delayed by 1.5hrs. Once inside, people had their small handbags on the storage. The crew (male guy) was not helpful in making some space in the storage. Instead, he asked few bags to be checked-in and it was not a great experience. No attempt to help but just followed the things with a straight face. People had their literally small bags and he wouldnt not move from one storage to another even if there was space and would not let us do i as well. Once flight was on, they ran out of Orange juice, really running out of orange juice when the temp were 32.degrees outside. didnt made the sense. Onasking for a extra snack, he made a face as if he was giving me out of his pocket. if the flight was delayed, there could have an attempt to provide something extra incase people did asked.

We did not fly on American Airlines from Chicago to London. We were rebooked on British Airways (by American Airlines) and our luggage was left behind. A full day delay and lost luggage.

I have posted the comments in the first flight leg.

First class snacks - stewardess gave out multiples to everyone until there was almost no selection left when she got back to me last in first class cabin. Nothing left that I would eat.

My feedback from the trip to Columbia to Chicago was meant for Chicago to Denver.

The WiFi was out gr entire flight. Had to Diane for almost 1 hour to wait for a gate to open up for plane to dock. Very bad experience.

After boarding, the AC was shut off on the flight. At business class, I really could not breathe. I was absolutely dripping sweat. I was told by the FA that there was nothing they could do but I could stand by the door until departure. So, that's what I did. I was clearly in the way while the FAs were trying to do their work, but I had to be able to breathe. After that, of course, I had sweated up a lot so was very uncomfortable for the six hour flight.

DELAYED AGAIN and AGAIN and AGAIN - not only that, you delay in 20 minute increments for hours and hours instead of having an accurate delay understanding.

AA was fine....the overall experience was subpar, but not due to the airline due to broader issues

No ground air conditioner for the plane. Very hot and humid prior to take off which was an uncomfortable period of time.

Check-in process was poor, very poor, only one person to check-in all passengers, so if one passenger had a check-in issue, all other passengers were delayed. All check-ins should have two airline staff to check-in passengers.

More options for your flight from Chicago to Trinidad and Tobago

Complete your trip to Trinidad and Tobago with a hotel stay or car rental