$195 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 4/21. 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

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

Sun, Apr 26 - Tue, Apr 28
Air Canada Logo
7:55 am - 12:20 am
ORD
-
POS
15h 25m
1 stop
Air Canada Logo
1:20 am - 1:05 pm
POS
-
ORD
12h 45m
1 stop
$427Air Canada
Sun, Apr 26 - Tue, Apr 28
Air Canada Logo
9:05 am - 12:20 am
ORD
-
POS
14h 15m
1 stop
Air Canada Logo
1:20 am - 2:55 pm
POS
-
ORD
14h 35m
2 stops
$436Air Canada
Sun, Apr 26 - Tue, Apr 28
Air Canada Logo
7:04 am - 12:20 am
ORD
-
POS
16h 16m
1 stop
Air Canada Logo
1:20 am - 1:05 pm
POS
-
ORD
12h 45m
1 stop
$438Air Canada
Sun, Apr 26 - Tue, Apr 28
Air Canada Logo
7:13 am - 12:20 am
ORD
-
POS
16h 07m
2 stops
Air Canada Logo
1:20 am - 2:55 pm
POS
-
ORD
14h 35m
2 stops
$439Air Canada
Sun, Apr 26 - Tue, Apr 28
Air Canada Logo
7:04 am - 12:20 am
ORD
-
POS
16h 16m
1 stop
Air Canada Logo
1:20 am - 8:05 pm
POS
-
ORD
19h 45m
2 stops
$441Air Canada
Wed, Apr 29 - Thu, May 7
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
$460Multiple Airlines
Fri, May 1 - Thu, May 7
Multiple Airlines Logo
5:05 am - 8:00 pm
ORD
-
POS
13h 55m
1 stop
Multiple Airlines Logo
9:10 am - 11:56 pm
POS
-
ORD
15h 46m
1 stop
$475Multiple Airlines
Wed, Apr 29 - Thu, May 7
Multiple Airlines Logo
6:40 pm - 12:20 am
ORD
-
POS
28h 40m
1 stop
Multiple Airlines Logo
9:10 am - 11:56 pm
POS
-
ORD
15h 46m
1 stop
$501Multiple Airlines
Wed, Apr 29 - Thu, May 7
Multiple Airlines Logo
2:09 pm - 12:20 am
ORD
-
POS
33h 11m
2 stops
Multiple Airlines Logo
9:10 am - 11:56 pm
POS
-
ORD
15h 46m
1 stop
$513Multiple Airlines
Sat, May 2 - Thu, May 7
Multiple Airlines Logo
3:52 pm - 6:55 pm
ORD
-
POS
26h 03m
1 stop
Multiple Airlines Logo
9:10 am - 11:56 pm
POS
-
ORD
15h 46m
1 stop
$525Multiple Airlines
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 $466, 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 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$190
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 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.

Reviews of the top 4 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.
7.5
Copa AirlinesOverall score based on 1575 reviews
7.4Comfort
6.8Entertainment
7.8Boarding
8.1Crew
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.

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.

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

Some of the Air hostesses are not that friendly. Need improvement

I liked the meatloaf the chicken was awful but the plane was on time and got there and the staff was nice.

They were super friendly bumped me up to exit row free of charge, All flight legs were on time

Boarding was quick & efficient; they gave boarding groups due priority; staff & air crew were very cordial and helpful, pleasant flight.

the food served was an embarrassment. No connection for charging the cellphone... What a crappy airline.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

The boarding timing needs to be improved. The flight was delayed again because it took way too long to board. I was already exhausted from sleeping at the airport and spending all day there due to delay from my previous flight that connected in Chicago.

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)

I almost missed my flight and they helped me out enormously

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.

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.

All good……but luggage didn’t make it on the airplane. Had to wait 3 days. Was a bummer.

Small suitcase used for carryon the last time was refused by boarding crew this time. Appears to be at the discretion and mood of the person on the day. Flight was only half booked, there would have been no problem with space.

It was a problem because there was a delay where we sat before taking off from newark,then when landed in Toronto we sat on tarmac and they wouldn't let us out for a long period of time. When we finally were released to the airport in Toronto the attendant scanned our boarding pass that we were here for our connection to Brazil. We ran all the way to the gate and they said at the gate the door is shut so we can not let you on the plane. We explained that we were checked in by the attendant when we arrived at Toronto airport to go to Brazil and they should not have shut the door. We were ignored at the gate

Flight home was delayed multiple times, did not get home until 2am

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)

My original flight was cancelled and then rebooked four hours later on a recovery flight, but I was checked in as stanby and had no seats so as a family of four we were concerned about not being seated altogether. Our flight then got delayed by another 1.5 hours and when seats were assigned at the gate, three of the four of us were together and we could get my wife closer, they offered no assistance.

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.

Everything you need to know for your flight to Trinidad

Information on your arrival and departure airports