$193 Find Cheap Flights from Chicago to Trinidad

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 departing on 10/28. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Trinidad

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Trinidad, 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 Trinidad, as well as popular online travel agencies
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Flight Deals

Book Cheap Chicago to Trinidad 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 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

Thu, Nov 20 - Fri, Nov 28
Air Canada Logo
2:00 pm - 1:10 amORD-POS
9h 10m1 stop
Air Canada Logo
2:15 am - 3:10 pmPOS-ORD
14h 55m1 stop
$433Air Canada
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Fri, Nov 21 - Fri, Nov 28
Air Canada Logo
6:05 pm - 1:10 amORD-POS
53h 05m2 stops
Air Canada Logo
2:15 am - 3:10 pmPOS-ORD
14h 55m1 stop
$443Air Canada
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Mon, Nov 10 - Mon, Nov 17
Multiple Airlines Logo
5:10 am - 8:00 pmORD-POS
12h 50m1 stop
Multiple Airlines Logo
2:26 pm - 9:47 amPOS-ORD
45h 21m2 stops
$448Multiple Airlines
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Tue, Nov 11 - Mon, Nov 17
Multiple Airlines Logo
6:40 am - 9:15 pmORD-POS
12h 35m1 stop
Multiple Airlines Logo
3:48 am - 9:47 amPOS-ORD
31h 59m2 stops
$455Multiple Airlines
Find Deal
Fri, Oct 24 - Mon, Oct 27
United Airlines Logo
6:00 am - 11:23 pmORD-POS
16h 23m1 stop
United Airlines Logo
12:30 am - 7:56 pmPOS-ORD
20h 26m1 stop
$549United Airlines
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Fri, Oct 24 - Tue, Oct 28
American Airlines Logo
6:45 am - 9:20 pmORD-POS
13h 35m2 stops
American Airlines Logo
7:00 am - 9:10 pmPOS-ORD
15h 10m2 stops
$553American Airlines
Find Deal
Thu, Nov 13 - Mon, Nov 17
American Airlines Logo
11:40 am - 11:39 pmORD-POS
9h 59m2 stops
American Airlines Logo
7:19 am - 5:45 pmPOS-ORD
12h 26m2 stops
$578American Airlines
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Sun, Mar 15 - Sat, Mar 21
Copa Airlines Logo
3:22 pm - 1:46 amORD-POS
9h 24m1 stop
Copa Airlines Logo
3:46 am - 1:31 pmPOS-ORD
10h 45m1 stop
$595Copa Airlines
Find Deal
Sun, Mar 15 - Fri, Mar 20
Copa Airlines Logo
3:22 pm - 1:46 amORD-POS
9h 24m1 stop
Copa Airlines Logo
3:46 am - 1:31 pmPOS-ORD
10h 45m1 stop
$598Copa Airlines
Find Deal
Tue, Mar 24 - Mon, Mar 30
United Airlines Logo
5:45 am - 11:23 pmORD-POS
16h 38m1 stop
United Airlines Logo
12:30 am - 9:25 amPOS-ORD
9h 55m1 stop
$659United Airlines
Find Deal
Booking Insights

KAYAK's insights & trends for Chicago to Trinidad flights

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

Can I save money by flying with a layover from Chicago O'Hare Intl Airport to Trinidad?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $406, prices are generally cheapest when you fly direct.

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

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, 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 is January, when tickets cost $528 (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?

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

When flying from Chicago to Trinidad, you should consider leaving on a Sunday and avoid Mondays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Thursdays and the most expensive ones on Wednesdays.

Good to know

Low seasonNovember
Cheapest flight$193
Best time to beat the crowds with an average 0% drop in price.
Most popular time to fly with an average 3% increase in price.
Flight from Chicago to Port of Spain

FAQs - booking Trinidad flights

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

    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.

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

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

    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 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?

    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 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?

    The cheapest time of day to fly to Trinidad 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 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

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Trinidad. 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 Trinidad? 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 8976 reviews
7.7Boarding
7.3Comfort
8.1Crew
7.1Entertainment
6.6Food
Airline reviews

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

8.0 ExcellentCynthia, Oct 2025ORD - PDX
Read more United Airlines reviews

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.

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

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

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

It was a smooth flight both in the sky and landing!

Pearson Airport could not properly handle all the passengers who they needed to process in order to properly get them on board. As a result, I missed the departure of my flight from Toronto. The only saving grace is that Air Canada found a flight that only delayed me by one hour. However, this was no thanks to Pearson Airport!

Almost everything it was a “cool” ambiance but we arrived to Toronto so that it’s ok for me

The crew was really nice. The plane seats were kinda small even for a 5’6” / 158 lbs person.

Fare was great, seat comfort the opposite as cushion was worn out. Ok for 2 hour flight, not for 4.5 hour flight..

Check in agent was very helpful and polite. He helped me board the earlier flight back home instead of waiting 2 hours at the airport for the next flight

Fair. What's the point of partnering with United if we cannot use the lounge. My wife is a frequent flier with United but we were refused access to Air Canada lounge

extremely cramped seating... absolutely no leg room and when person in front of me reclined... I was pinned in my seat... absolutely ridiculous

Didn’t realize I purchased a basic fare with no carry ons allowed. Not very well communicated. Also had seats switched without knowledge and had to pay for different ones.

We loved our Air Canada experience and will definitely fly them again. It just so happened than in the first leg of our trip their entertainment system was not working, and neither was their oven so cold meal & snacks only.

Everything you need to know for your flight to Trinidad

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