$237 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 2/25. 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

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

Fri, Feb 27 - Mon, Mar 2
JetBlue Logo
12:41 pm - 7:17 am
ORD
-
POS
16h 36m
1 stop
JetBlue Logo
9:05 am - 9:10 am
POS
-
ORD
26h 05m
2 stops
$396JetBlue
Mon, Feb 23 - Fri, Mar 6
Air Canada Logo
8:40 pm - 1:20 am
ORD
-
POS
26h 40m
1 stop
Air Canada Logo
2:20 am - 3:10 pm
POS
-
ORD
14h 50m
1 stop
$417Air Canada
Wed, Feb 25 - Tue, Mar 3
Air Canada Logo
8:40 pm - 1:20 am
ORD
-
POS
26h 40m
1 stop
Air Canada Logo
2:20 am - 2:55 pm
POS
-
ORD
14h 35m
2 stops
$421Air Canada
Mon, Feb 23 - Fri, Mar 6
Air Canada Logo
8:40 pm - 1:20 am
ORD
-
POS
26h 40m
1 stop
Air Canada Logo
2:20 am - 6:52 pm
POS
-
ORD
18h 32m
2 stops
$422Air Canada
Sun, Mar 8 - Sun, Mar 15
Air Canada Logo
7:15 am - 12:20 am
ORD
-
POS
16h 05m
2 stops
Air Canada Logo
1:20 am - 6:52 pm
POS
-
ORD
18h 32m
2 stops
$426Air Canada
Mon, Feb 23 - Fri, Mar 6
Air Canada Logo
6:04 pm - 1:20 am
ORD
-
POS
29h 16m
2 stops
Air Canada Logo
2:20 am - 6:52 pm
POS
-
ORD
18h 32m
2 stops
$427Air Canada
Sun, Mar 8 - Sun, Mar 15
Air Canada Logo
10:00 am - 12:20 am
ORD
-
POS
13h 20m
1 stop
Air Canada Logo
1:20 am - 8:10 pm
POS
-
ORD
43h 50m
2 stops
$431Air Canada
Thu, Mar 12 - Tue, Mar 17
Air Canada Logo
10:00 am - 12:20 am
ORD
-
POS
13h 20m
1 stop
Air Canada Logo
1:20 am - 1:01 pm
POS
-
ORD
12h 41m
1 stop
$447Air Canada
Thu, Mar 12 - Tue, Mar 17
Air Canada Logo
10:00 am - 12:20 am
ORD
-
POS
13h 20m
1 stop
Air Canada Logo
1:20 am - 2:55 pm
POS
-
ORD
14h 35m
2 stops
$451Air Canada
Thu, Mar 12 - Tue, Mar 17
Air Canada Logo
7:15 am - 12:20 am
ORD
-
POS
16h 05m
2 stops
Air Canada Logo
1:20 am - 2:55 pm
POS
-
ORD
14h 35m
2 stops
$454Air Canada
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 $422, 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 December and April, when the average cost of round-trip tickets is $767 and $753 respectively.

Good to know

Low seasonApril
Cheapest flight$237
Best time to beat the crowds but there is an average 21% increase in price.
Most popular time to fly with an average 2% 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 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 9149 reviews
7.1Entertainment
7.3Comfort
7.7Boarding
6.6Food
8.1Crew
Airline reviews

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

6.0 GoodPatricia, Jan 2026
ORD - LAS
Read more United Airlines reviews

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Not United Airlines' fault. It's ORL airport's fault.

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

The movies offered were great. Staff were very pleasant and very efficient.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very nice flight love the small aircraft. We had a wonderful flight attendant. Nice to see someone that really enjoys her job. Don't have her name but had a southern accent.

We experienced gate changes and a long delay. My seat was dirty when I boarded and I had to use wipes to clean it myself. There was an unpleasant and overpowering cleaning product scent on the plane as well that lingered through the flight.

My carry on baggage was damaged. Entire trip, I had to carry the baggage. When complained to the boarding crew, they got mad at me and still asked me to valet check in the cabin baggage. Rude boarding crew!!!

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

The boarding by groups is pointless. The first two groups worked fine, but almost Noone boarded in goups three thru five leaving the vast majority boarding when group six was called. It defeated the purpose of spreading out the crowd.

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!

I waiting for 2 hrs to retrieve my luggage. Didn't get home till 3am.

The flight left late and I didn’t get a glass of bubbly upon boarding (which I’m used to when booking business class on other flights), but otherwise it was a pleasant flight with lovely, helpful crew members and I enjoyed my meal.

Flight cancellations, delays, mass confusion and disorganization! That’s Air Canada for you, nothing new. I would have chosen a different airline if it were an option, and Air Canada continues to prove they don’t care about their customers.

everything was fine. but paying for 1 piece of check-in luggage and denying passengers to board with carry-on luggage which by air line's standards does not fit is not acceptable. when one travels for a longer time one needs to have some essentials

Couldn't fit knees, only 1 toilet working, didn't get anything to drink cause the stewards were not able to get to us

Flight was canceled for a reason they knew hours before but did not mention. Next the gate chnage from 37 to 38 at least 10 times. Ridiculous.

The flight from SFO to YVR was delayed and my bag did not make it to my next flight from YVR to SYD. It took almost 3 days after I landed to get my bag and when I got it, it was filled with dust

Our biggest complaint about Air Canada is that if you don’t like your seat during check-in, there’s a fee to move elsewhere. On our flight from YUL to FFL, we were charged to change seats—just regular seats. What’s maddening is that the plane wasn’t even full; there were even a few people sleeping in the middle row sections (entire rows, completely empty), using them as beds. In my opinion, charging passengers for seat changes is a cash grab by Air Canada. They are definitely not the airline they were back in the day. I suppose they need to gouge the consumer now that they pay their attendants while on ground. One out of 10.

Nothing specific. Cabin temperature was too high for some reason.

It was just fine. I managed to make all my connection too sbut had trouble in Munich with no wheel chair and trouble trying to get help from the airport people to get to the other terminal for my flight. Finally a wonderful lady Amelia, helped me to make my flight connection Timon with zero time to spare.

Everything you need to know for your flight to Trinidad

Information on your arrival and departure airports