$174 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 2/28. 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, 0 bags

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Cheap Flights from Chicago to Trinidad and Tobago

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Port of Spain
Port of Spain1 stop$413
Scarborough
Scarborough2 stops$1,385
Port of Spain
Port of Spain1 stop$413
Scarborough
Scarborough2 stops$1,385

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

Sat, Jan 24 - Sat, Jan 31
Multiple Airlines Logo
8:45 pm - 1:20 am
ORD
-
POS
26h 35m1 stop
Multiple Airlines Logo
8:20 am - 5:25 pm
POS
-
ORD
35h 05m2 stops
$413Multiple Airlines
Sat, Jan 24 - Sat, Jan 31
JetBlue Logo
7:45 am - 7:11 pm
ORD
-
POS
33h 26m2 stops
JetBlue Logo
8:20 am - 5:25 pm
POS
-
ORD
35h 05m2 stops
$420JetBlue
Mon, Jan 12 - Thu, Jan 15
Air Canada Logo
6:00 pm - 1:20 am
ORD
-
POS
29h 20m2 stops
Air Canada Logo
2:20 am - 1:01 pm
POS
-
ORD
12h 41m1 stop
$423Air Canada
Tue, Jan 13 - Wed, Jun 3
Air Canada Logo
7:15 am - 1:20 am
ORD
-
POS
16h 05m2 stops
Air Canada Logo
1:25 am - 6:33 pm
POS
-
ORD
18h 08m2 stops
$427Air Canada
Thu, Jan 29 - Tue, Apr 7
Multiple Airlines Logo
8:00 am - 1:20 am
ORD
-
POS
15h 20m1 stop
Multiple Airlines Logo
3:40 pm - 9:10 am
POS
-
ORD
18h 30m2 stops
$447Multiple Airlines
Thu, Mar 12 - Tue, Mar 17
Air Canada Logo
2:00 pm - 12:20 am
ORD
-
POS
9h 20m1 stop
Air Canada Logo
1:20 am - 3:10 pm
POS
-
ORD
14h 50m1 stop
$453Air Canada
Tue, Jan 13 - Wed, Jun 3
Multiple Airlines Logo
9:23 am - 6:55 pm
ORD
-
POS
31h 32m1 stop
Multiple Airlines Logo
9:10 am - 6:15 pm
POS
-
ORD
10h 05m1 stop
$454Multiple Airlines
Fri, Mar 13 - Tue, Mar 17
Air Canada Logo
7:15 am - 12:20 am
ORD
-
POS
16h 05m2 stops
Air Canada Logo
1:20 am - 6:52 pm
POS
-
ORD
18h 32m2 stops
$457Air Canada
Mon, Jan 26 - Mon, Feb 2
JetBlue Logo
7:45 am - 7:11 pm
ORD
-
POS
33h 26m2 stops
JetBlue Logo
8:20 am - 5:43 pm
POS
-
ORD
35h 23m2 stops
$459JetBlue
Fri, Mar 27 - Fri, Apr 3
Multiple Airlines Logo
6:22 pm - 1:36 pm
ORD
-
POS
18h 14m2 stops
Multiple Airlines Logo
1:20 am - 6:53 pm
POS
-
ORD
42h 33m2 stops
$466Multiple 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 December and April, when the average cost of round-trip tickets is $795 and $753 respectively.

Good to know

Low seasonApril
Cheapest flight$174
Best time to beat the crowds but there is an average 21% 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.

  • 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 9113 reviews
8.1Crew
7.1Entertainment
6.6Food
7.7Boarding
7.3Comfort
Airline reviews

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.

6.0 GoodMarco, Dec 2025
ORD - ORF
Read more United Airlines reviews

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.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Seats in waiting area and on plane hard as rock. Fast internet on the flight was great! Crew was kind.

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!

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

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.

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.

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

Information on your arrival and departure airports