$178 Find Cheap Flights from Chicago to Trinidad and Tobago

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 Trinidad and Tobago departing on 12/7. 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.
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Book Cheap Chicago to Trinidad and Tobago Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Trinidad and Tobago 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 Trinidad and Tobago

Mon, Dec 8 - Fri, Dec 12
Multiple Airlines Logo
5:00 am - 8:00 pmORD-POS
13h 00m1 stop
Multiple Airlines Logo
10:10 am - 12:09 amPOS-ORD
15h 59m1 stop
$418Multiple Airlines
Find Deal
Mon, Dec 8 - Fri, Dec 12
Multiple Airlines Logo
7:10 am - 8:00 pmORD-POS
10h 50m1 stop
Multiple Airlines Logo
10:10 am - 12:09 amPOS-ORD
15h 59m1 stop
$424Multiple Airlines
Find Deal
Wed, Dec 3 - Thu, Dec 11
Multiple Airlines Logo
8:15 pm - 1:10 amORD-POS
26h 55m1 stop
Multiple Airlines Logo
9:10 am - 6:36 pmPOS-ORD
11h 26m1 stop
$455Multiple Airlines
Find Deal
Sat, Nov 22 - Fri, Nov 28
Air Canada Logo
8:15 pm - 1:10 amORD-POS
26h 55m1 stop
Air Canada Logo
2:15 am - 1:01 pmPOS-ORD
12h 46m1 stop
$483Air Canada
Find Deal
Sat, Nov 22 - Fri, Nov 28
Air Canada Logo
8:15 pm - 1:10 amORD-POS
26h 55m1 stop
Air Canada Logo
2:15 am - 6:55 pmPOS-ORD
18h 40m2 stops
$488Air Canada
Find Deal
Mon, Nov 17 - Wed, Dec 3
JetBlue Logo
6:45 am - 3:07 pmORD-POS
30h 22m1 stop
JetBlue Logo
5:42 pm - 9:52 pmPOS-ORD
30h 10m1 stop
$511JetBlue
Find Deal
Mon, Dec 8 - Thu, Dec 11
United Airlines Logo
10:35 am - 12:23 amORD-POS
11h 48m1 stop
United Airlines Logo
1:30 am - 11:11 amPOS-ORD
11h 41m1 stop
$549United Airlines
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Wed, Jan 14 - Tue, Jan 20
American Airlines Logo
6:54 am - 10:48 pmORD-POS
13h 54m2 stops
American Airlines Logo
6:30 am - 7:50 pmPOS-ORD
15h 20m2 stops
$553American Airlines
Find Deal
Thu, Mar 12 - Wed, Mar 18
American Airlines Logo
7:20 pm - 1:51 pmORD-POS
17h 31m2 stops
American Airlines Logo
3:34 pm - 12:14 amPOS-ORD
9h 40m1 stop
$558American Airlines
Find Deal
Sun, Feb 15 - Sun, Feb 22
United Airlines Logo
2:30 pm - 1:05 amORD-POS
8h 35m1 stop
United Airlines Logo
1:30 am - 10:07 amPOS-ORD
10h 37m1 stop
$651United Airlines
Find Deal
Booking Insights

KAYAK's insights & trends for Chicago to Trinidad and Tobago flights

Get data-powered insights and trends into flights from Chicago to Trinidad and Tobago to help you find the cheapest flights, the best time to fly and much more.

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

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 Trinidad and Tobago, 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 Trinidad and Tobago is November, when tickets cost $443 (return) on average. On the other hand, the most expensive months are December and July, when the average cost of round-trip tickets is $763 and $692 respectively.

What’s the cheapest day of the week to fly from Chicago to Trinidad and Tobago?

The average price of all round-trip flights from Chicago O'Hare Intl Airport to Trinidad and Tobago clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Chicago to Trinidad and Tobago, look for departures on Sundays and avoid leaving on a Monday, as it's usually the priciest day. When flying back from Trinidad and Tobago, Thursday is the cheapest day to fly and Wednesday is the most expensive.

Good to know

Low seasonApril
Cheapest flight$178
Best time to beat the crowds but there is an average 13% increase in price.
Most popular time to fly with an average 5% increase in price.
Flight from Chicago to Port of Spain

FAQs - booking Trinidad and Tobago flights

  • How does KAYAK find such low prices on flights from Chicago to Trinidad and Tobago?

    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 Trinidad and Tobago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Trinidad and Tobago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Chicago to Trinidad and Tobago 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 Trinidad and Tobago?

    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 from Chicago to Trinidad and Tobago with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Trinidad and Tobago?

    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 from Chicago to Trinidad and Tobago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest time of day to fly to Trinidad and Tobago?

    The cheapest time of day to fly to Trinidad and Tobago is generally in the evening, when round-trip flights cost $533 on average. Morning departures are around 18% more expensive than evening flights, on average. The most expensive time of day to fly to Trinidad and Tobago is generally at night, which is peak travel time and where the average cost of a ticket is $905.

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 9001 reviews
8.1Crew
7.1Entertainment
7.7Boarding
7.3Comfort
6.6Food
Airline reviews

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

10.0 ExcellentDr. Joseph, Oct 2025ORD - STL
Read more United Airlines reviews

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

Not the fault of United—weather, reroute around weather, time sitting on tarmac, arrived couple hours late, too late for train into city necessitating a much pricier cab but weather…can’t be helped.

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

The flight attendants were rude. Seemed like they didn’t want to be there. Except for one girl that was really nice. Seats are sooooo uncomfortable. They give you a piece of paper and a thin cushion for a pillow and blanket that does nothing. Airlines have gone way downhill, especially United international flights. Food was disguting. Definitely flying ANA next time.

Crew and customer service were excellent. This flight also had plenty of leg room and seat mounted screens for entertainment. A very pleasant flight all around!

It would have been better if the crew has supported my husband's reasons for needing to keep the space clear around his feet, rather than insisting that he put his knapsack in that space.

Subject: Formal Complaint: Discriminatory and Unprofessional Conduct – Request for Immediate Action & Compensation Dear [Airline Customer Relations Team], I am writing to file a formal complaint regarding my recent travel experience with [Airline], which was by far the worst I have ever encountered. What occurred was not only unprofessional, but in several instances discriminatory, unsafe, and unacceptable. On the first leg of my trip, I arrived only four minutes past check-in. Instead of making any attempt to resolve the matter, your representative flatly denied me boarding and made me wait while she attended to passengers who arrived after me. By the time a manager intervened, it was too late to board, costing me time, money, and unnecessary frustration. The second leg of my trip (Chicago–San Francisco) raised even more serious concerns. From the outset, it was apparent that the staff—particularly two attendants—prioritized Caucasian passengers while dismissing African American and minority passengers. • When a Caucasian passenger in the exit row refused to comply with federal safety requirements, I, as a first responder, immediately offered to switch seats and assume the responsibility. My offer was blatantly ignored, and instead, a Caucasian passenger seated further up was chosen. This was discriminatory and deeply insulting, especially as I was actively de-escalating the situation that could have delayed the flight further. • During a lengthy tarmac delay of over 90 minutes, passengers were given conflicting and unreasonable instructions that created unnecessary distress and tension. • Throughout the flight, a visibly intoxicated passenger directly in front of me was disruptive, rude to others, failed to comply with seatbelt and electronic device rules, and yet faced no enforcement from the crew. In stark contrast, I was singled out for repeated compliance checks even though I was following every rule. This unequal treatment was so obvious that multiple passengers around me spoke up in my defense. This pattern of behavior demonstrated a clear lack of professionalism, disregard for passenger safety, and discriminatory treatment. I expect far better from an airline of your stature. As a paying customer subjected to this unacceptable treatment, I am formally requesting: 1. A full investigation into the conduct of the staff on both flights. 2. A written apology acknowledging the discriminatory and unprofessional behavior I endured. 3. Appropriate compensation for the distress, inconvenience, and mishandling of my travel. If this matter is not addressed promptly and thoroughly, I will have no choice but to escalate my complaint further, including filing with the U.S. Department of Transportation and sharing my experience through other channels. I trust [Airline] will take this complaint seriously and provide a timely resolution.

Check in was quick and easy during early hours. Flight was on time, and customer services was a plus.

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

We had a layover from YVR to Denver. We bought 4 bottles of Absolut Vodka at the YVR Duty Free for $116.20, after going through security and American Customs Pre Clearance at YVR, Vancouver. When we landed in Denver, United put us behind the American Customs as well as TSA again for some reason. We were forced to go through American Customs and TSA again. TSA confiscated our rightfully owned Duty Free Absolut Vodka bottles. Because United incorrectly forced our flight behind American border and TSA again, we missed the connecting flight. After United put us on a later flight, we eventually arrived in Chicago very late, with hardly any sleep. I am looking for compensation from United for our incorrectly confiscated Absolut Vodka bottles worth $116.20, as well as compensation for incorrectly putting us behind American Customs and TSA again, causing us to miss our connecting flight, making us arrive extremely late in Chicago.

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

My wife and I love to travel, so we fly a lot. We've already logged 381,075 miles and with practically every major airline. But this flight was very disappointing. It started off well, with no delays and a new plane. But when lunchtime approached, all that good impression was ruined. Instead of white tablecloths, we were offered small, dark placemats, which, as it turned out, were perfectly adequate for the food. All the food offered—and my wife and I only took fish, and the meat—was not just bad, it was downright disgusting and not heated enough. The same applies to the appetizers. This was the first time in many years of traveling that we've been offered such disgusting food.

Lost luggage stuck no clothes and no word after 2 days leaving on cruise no stuff or clothes

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Over 40 years ago my AC return flight was canceled, during this last summer the same thing happened. AC denied everything Canadian like paying for accommodations and basic necessities. So why would I ever want to fly AC again? This last flight my wife took the return flight had problems and left late, so I guess they are getting better. However I have no faith in this airline so I drove to this last destination! I'll never fly AC again!!!

Great check in process in LA and good service The check in process as well as at the gate is way better in the US versus canada 🇨🇦

Super experience. Earlier than schedule departure and arrival. Baggage handling was very good

Allow me to book extra bag check in as free though I packed in 1 luggage but that was 7 LBS overweight so make another bag to free check in.

I would like to get my money back. I flight was 4 hours late on the way to detroit, And same on my way back to Brussels they cancelled my flight and give me an other ticket and i had to wait 5 hours.

All attendents were very efficient, pleasant and happy. Everything went smoothly. The seats could have been wider. There could have been more free food instead of just one small bar.

My seat was one of those that couldn't recline, but the problem was that it was abnormally upright, so the headrest actually made the seat concave, which was uncomfortable and hard on my lower back. I had to ball my jacket up and use it as lumbar support. goodness I had it with me.

Boarding was so so after zone 3 was called all other zones went in

I liked a lot , the flight attendant so nice ,the seat very comfortable I enjoyed the flight , I will do it again with Air Canada,

Plane left an hour late, I missed my connection and my bow case was never even loaded on the plane in VA. I deal with this type of nonsense everytime I fly air canada.

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