$180 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 4/25. 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

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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

Fri, Apr 17 - Fri, Apr 24
Copa Airlines Logo
8:06 am - 1:10 pm
ORD
-
POS
28h 04m
1 stop
Copa Airlines Logo
2:17 pm - 1:13 am
POS
-
ORD
11h 56m
1 stop
$384Copa Airlines
Fri, Apr 17 - Sun, Apr 19
Air Canada Logo
7:55 am - 12:20 am
ORD
-
POS
15h 25m
1 stop
Air Canada Logo
1:20 am - 6:58 pm
POS
-
ORD
18h 38m
2 stops
$417Air Canada
Sun, Apr 19 - Tue, Apr 21
Air Canada Logo
8:40 am - 12:20 am
ORD
-
POS
14h 40m
2 stops
Air Canada Logo
1:20 am - 6:58 pm
POS
-
ORD
18h 38m
2 stops
$421Air Canada
Tue, Apr 21 - Fri, Apr 24
Multiple Airlines Logo
9:50 am - 12:20 am
ORD
-
POS
13h 30m
1 stop
Multiple Airlines Logo
10:10 am - 12:24 am
POS
-
ORD
15h 14m
1 stop
$437Multiple Airlines
Sat, May 2 - Thu, May 7
Multiple Airlines Logo
6:40 am - 6:55 pm
ORD
-
POS
11h 15m
1 stop
Multiple Airlines Logo
9:10 am - 11:56 pm
POS
-
ORD
15h 46m
1 stop
$457Multiple Airlines
Sat, May 2 - Wed, May 6
Multiple Airlines Logo
6:40 am - 6:55 pm
ORD
-
POS
11h 15m
1 stop
Multiple Airlines Logo
9:10 am - 4:50 pm
POS
-
ORD
32h 40m
1 stop
$461Multiple Airlines
Sat, Apr 25 - Fri, May 8
Multiple Airlines Logo
1:27 pm - 8:00 pm
ORD
-
POS
29h 33m
1 stop
Multiple Airlines Logo
10:10 am - 11:59 pm
POS
-
ORD
14h 49m
1 stop
$465Multiple Airlines
Sun, Apr 26 - Fri, May 8
Multiple Airlines Logo
5:05 am - 8:00 pm
ORD
-
POS
13h 55m
1 stop
Multiple Airlines Logo
10:10 am - 11:59 pm
POS
-
ORD
14h 49m
1 stop
$466Multiple Airlines
Mon, Jun 1 - Fri, Jun 5
Multiple Airlines Logo
8:05 am - 8:00 pm
ORD
-
POS
10h 55m
1 stop
Multiple Airlines Logo
10:10 am - 12:37 pm
POS
-
ORD
27h 27m
1 stop
$467Multiple Airlines
Wed, Apr 29 - Mon, May 4
Multiple Airlines Logo
4:15 pm - 12:20 am
ORD
-
POS
31h 05m
1 stop
Multiple Airlines Logo
9:10 am - 11:56 pm
POS
-
ORD
15h 46m
1 stop
$470Multiple Airlines
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 April and December, when the average cost of round-trip tickets is $794 and $750 respectively.

Good to know

Low seasonJanuary
Cheapest flight$180
Best time to beat the crowds but there is an average 1% increase in price.
Most popular time to fly with an average 6% 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.

Reviews of the top 4 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.
7.5
Copa AirlinesOverall score based on 1575 reviews
8.1Crew
6.8Entertainment
7.7Boarding
7.4Comfort
6.8Food
Airline reviews

Entire experience from check in to landing was amazing the flight crew was excellent and friendly. Seats were comfortable.

10.0 ExcellentK Anson, Apr 2026
POS - PTY
Read more Copa Airlines reviews

Entire experience from check in to landing was amazing the flight crew was excellent and friendly. Seats were comfortable.

Friendly crew, good food options, food not the best and seats not as comfy but that’s typical.

The food is terrible I ask for water never got transport my mother we’re late and my sister from Lima was the worst waiting to long for wheelchair

Copa staff at PTY and one particular crew member were unhelpful & rude.

Seats were awful. Media should have been included for such a long flight.

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

Horrible. No TV or any type of entertainment on board. Passwnger listening to/watching stuff on their own phone with no headphones making it noise and uncomfortable for everyone else, little/tiny food portions, old seats, useless wifi (cant access anything). Horrible exlerience especially it was a lomg distance flight with kids.

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.

Very strict carry on rules meant most of the plane had to gate check their luggage. As is often the case had things that were broken because of this, but I appreciated not being charged to gate check. Otherwise good flight and great crew once on the plane

Simply as follows:- First, there was no vegetarian option for the meal Second, only 2 washrooms for the entire economy class.

Great until we got to FRA. The next trip leg we were put in Business Class where seats had minimal padding!!!! They were awful and United Airlines needs to have their Lufthansa partner up their game or I won’t fly with them again!!

No meal service to the back of the plane as it started late or was too slow to get it out before it was time to land.

Terrible, if possible won't be flying again anytime soon!

Efficient boarding and early departure. Very smooth flight. Early arrival in ATL. Great flight.

Smooth and easy boarding, comfortable for the entire 5 hour flight, and the seat back entertainment was great! I appreciated all the features, from location info and maps, movies, the ability to connect with Bluetooth headphones, and good selection of movies. Food was good, normal airline snacks (I didn’t purchase anything)

Awful. No counter attendants. No dinner offered due to delays.

This trip did not start off well. The inbound flight was delayed about 20 minutes. Then, after initial onboarding, the passengers had to deplane due to a mechanical problem. That took about 30 minutes to fix and be cleared. Then, reboarding was chaotic. It took a long time to sort passengers and two passengers on standby were ticketed but there was no seat. So, they had to deplane. One of the flight crew was trying to help passengers figure out a place to put their carry-on bags and that took more time. In the end, our scheduled 10:30 am departure did not actually take off until about 12:05 pm CST. The flight itself was long but we got to Houston. Some passengers missed their connecting flights and had to rebook. Not the best of flights I've had.

We were delayed for about an hour from taking off due to traffic control procedures at the destination airport. But once in the air, the flight went well. The crew members were great and provided cabin service despite moderate turbulence during much of the flight.

Short flight, but no drink/snack service. The flights both going and coming were delayed.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Moved to earlier flight which unexpectedly had maintenance issues initially indicated as quick fix to ultimately plane changes. Moved back to original flight, also delayed. In all cases customer updates and communication very unclear, no updates on drivers for delays.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

Pretty awful. 2 hours late due to operational issues and finally deboarded around 2am.

The gate got changed several times and the flight was delayed over an hour. Awful experience

American continues to decline in their customer service and its beyond disappointing.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

As previously stated the delay I experienced flying from Wichita to Chicago caused a host of issues. When I finally was able to be booked on the last remaining American flight from Chicago to Cincinnati, the gate changed four times with the last change occurring very near the scheduled boarding time. While I didn't have a problem moving from gate to gate, I did notice and make note of others that had mobility issues and had to move each time for the gate change.

Maintenance took a very long time and then we were in a holding pattern. While a one-off maintenance issue is standard, there were delays on both of my flights for this trip based on maintenance issues with the planes, which delayed both flights over 45 minutes. Thankfully, I didn't have any connections but it wasn't an experience that would make me pick AA if I have other options.

I bought a ticket from Kayak. When I got to the airport, the was no ticket. I had to pay 5X to get to my destination. No response received from Kayak. I will NEVER use them again.

My wallet was stolen while I was sleeping on the plane.

Good boarding but extremely cold temperature in both flights (60 F!).

The whole plane smelled and felt old. The seats were very uncomfortable. Multiple delays. Extra fees.

Very rude gate attendants in San Francisco who didn’t let me bring my little carry on (smaller than usual size) and after boarding I realized that there still were a lot of overhead compartment space (like a full section available in some spots). That made me lose 30 minutes at my destination at 1am and it could have broken something fragile that I had in it

The most uncomfortable flight I’ve ever been on. I’m only 5,4” and barely had enough room to exist, couldn’t even fully relax my shoulders. Not sure why they bother with snacks. Half a coke and a single cookie?? Wow. Purchasable food looked gross too. Remember when airlines used to treat you like a human being?

Departed Palm Springs over an hour late because there’s only one gate, and it has always delayed by the arriving and departing flight to Toronto and the arriving flight from Vancouver.

I checked a bag and there was only one agent to assist all customers with any issues.

I want to thank Carlos at the Miami AC desk - he was amazing and went over and above to help us out. Thank you Carlos and all the best to you!!! You made our faith in AC feel great! Sincerely, David Cubitt

Flight was canceled due to mechanical issues. After a considerable wait in the queue, Air Canada customer service was very helpful to get us on another flight. I am disappointed to report our rescheduled flight is for three days from now. Three days of extra expenses and inconvenience is unacceptable.

Everything you need to know for your flight from Chicago to Trinidad and Tobago

Information on your arrival and departure airports