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Cheap Flights from Chicago to Trinidad and Tobago

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Port of Spain
Port of Spain1 stop$625
Scarborough
Scarborough2 stops$1,161
Port of Spain
Port of Spain1 stop$625
Scarborough
Scarborough2 stops$1,161
Booking Insights

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 $625 round-trip, to Port of Spain Piarco Intl (POS).

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

March is the cheapest time of year to fly, with average fares of $593. Prices are highest in October, when average flight costs increase to around $887.

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 23% 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

$295
Beat the crowds with an average 68% drop in travelers.
The most popular month to fly with an average 91% 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 $610 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 $610 to $781.

  • What are the main airports serving Trinidad and Tobago?

    Flights to Trinidad and Tobago use two main airports, Port of Spain Piarco Intl (POS) and Scarborough ANR Robinson Intl (TAB).

  • 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 United Airlines and American Airlines.

  • 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 book Economy Class or First 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 March when flights are typically cheapest and avoid October when prices are at their highest.
  • Flying on Friday is usually the cheapest. Flights on Monday cost about 23% 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 airlines flying 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.
7.3
United AirlinesOverall score based on 10461 reviews
7.1Entertainment
7.3Comfort
8.1Crew
6.7Food
7.7Boarding
Airline reviews

Connection times always good online, but not in reality when first leg is delayed (2 out of 2 times this trip).

6.0 GoodJoann, Oct 2026
Read more United Airlines reviews

Connection times always good online, but not in reality when first leg is delayed (2 out of 2 times this trip).

It was good flight was smooth, little cold on the plane but other wise good.

Great flight and crew. Need more legroom and DO NOT allow seats to recline.

The guy in front of me was talking constantly, even when the pilot was making announcements. I found this very disrespectful to the pilot and to others.

We left 1.5 hours late due to a “maintenance” issue. Very poor communication as to when we would board & depart. The crew in First Class was uncharacteristically not friendly). Delay into Brussels cost me my connection to Rome so lost the entire first day of vacation ( had a 10:30am flight to Rome - ended up on a 6:55pm flight).

Everything was OK except the meals, that was overpriced chicken meat.

Miss My connection I had to take a flight from Indianapolis to Denver , then to san fransisco , sleep in sans fransisco en the flight to Los Cabos the next morning

The TVs on the plane were all broken and inoperable. No snacks or food were served. Plane was very old and uncomfortable.

Takeoff delayed 2 hrs. Boarded on time to find we were missing part of the flight crew. Then informed that they had loaded too much fuel. Spent 1 1/2 hrs sitting there burning off the excess, which included a couple of laps around the runway until we were light enough to fly! Ridiculous!

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.

Flight was fine. Just delays leaving due to mechanical issues. But flight crew were kind and professional. Seats were spacious. American doesn't need to have 9 groups for boarding.

Both departure and return flights had mechanical delays. Their planes are antiquated resulting in a two hour flight taking almost four hours to complete.

Crew were helpful, pilot kept us informed about turbulence, snack choice was awesome!

It was one of the worst I have ever had. The plane was over booked, and I did not have a seat. When I questioned why because I had booked this weeks in advance. I was brushed off to be advised they are trying to find someone to give up their seat. Only to be advised I would be boarding last. I had priority boarding in group 1-4. When I asked why I had to be last because that is not what I paid for I was advised it doesn't matter you will get a seat. The ticket person was very rude and unprofessional. The gate changed several times and it was going from one area to another area far away from where we were at. I feel like I should have been compensated in some kind of way because of the way I was treated. The ticket agent acted like it was my fault that the plane was over booked. Not one time was I apologized to for this inconvenience.

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.

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