$202 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 5/17. 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$384
Scarborough
Scarborough2 stops$1,134
Port of Spain
Port of Spain1 stop$384
Scarborough
Scarborough2 stops$1,134

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

Wed, Apr 15 - Fri, Apr 17
Copa Airlines Logo
3:05 pm - 1:40 am
ORD
-
POS
9h 35m
1 stop
Copa Airlines Logo
2:17 pm - 1:13 am
POS
-
ORD
11h 56m
1 stop
$384Copa Airlines
Thu, Apr 9 - Sun, Apr 12
Air Canada Logo
9:50 am - 12:20 am
ORD
-
POS
13h 30m
1 stop
Air Canada Logo
1:20 am - 5:50 pm
POS
-
ORD
17h 30m
1 stop
$388Air Canada
Tue, Apr 7 - Sun, Apr 12
Air Canada Logo
2:00 pm - 12:20 am
ORD
-
POS
9h 20m
1 stop
Air Canada Logo
1:20 am - 9:50 am
POS
-
ORD
9h 30m
1 stop
$393Air Canada
Wed, Apr 8 - Sun, Apr 12
Air Canada Logo
6:21 pm - 12:20 am
ORD
-
POS
28h 59m
2 stops
Air Canada Logo
1:20 am - 7:58 am
POS
-
ORD
31h 38m
2 stops
$398Air Canada
Sat, Apr 4 - Sun, Apr 12
Air Canada Logo
6:40 pm - 12:20 am
ORD
-
POS
28h 40m
1 stop
Air Canada Logo
1:20 am - 5:50 pm
POS
-
ORD
17h 30m
1 stop
$413Air Canada
Sat, Apr 4 - Sun, Apr 12
Air Canada Logo
3:45 pm - 12:20 am
ORD
-
POS
31h 35m
2 stops
Air Canada Logo
1:20 am - 5:50 pm
POS
-
ORD
17h 30m
1 stop
$416Air Canada
Wed, Apr 8 - Fri, Apr 10
Air Canada Logo
9:20 pm - 12:20 am
ORD
-
POS
26h 00m
1 stop
Air Canada Logo
1:20 am - 1:05 pm
POS
-
ORD
12h 45m
1 stop
$418Air Canada
Thu, Apr 2 - Thu, Apr 9
Air Canada Logo
1:55 pm - 12:20 am
ORD
-
POS
33h 25m
2 stops
Air Canada Logo
1:20 am - 6:58 pm
POS
-
ORD
18h 38m
2 stops
$423Air Canada
Mon, Apr 6 - Thu, Apr 9
Air Canada Logo
6:01 pm - 12:20 am
ORD
-
POS
29h 19m
2 stops
Air Canada Logo
1:20 am - 8:03 am
POS
-
ORD
31h 43m
1 stop
$426Air Canada
Sun, Apr 26 - Sun, May 3
Multiple Airlines Logo
9:05 am - 12:20 am
ORD
-
POS
14h 15m
1 stop
Multiple Airlines Logo
5:38 pm - 9:36 pm
POS
-
ORD
28h 58m
2 stops
$468Multiple 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 $1,059 and $767 respectively.

Good to know

Low seasonJanuary
Cheapest flight$202
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly with an average 2% 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 1567 reviews
6.8Entertainment
7.4Comfort
7.8Boarding
8.1Crew
6.8Food
Airline reviews

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

6.0 GoodOluwaseyi, Feb 2026
PTY - POS
Read more Copa Airlines reviews

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.

Very happy with my flight. I would definitely recommend it.

Did upgrade, travel in business it was great (more room I could sleep)

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

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

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. :/

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.

No Snacks or Entertainment. The flight was short, snacks should still be given.

See prior comment about how Kayak mishandled my reservation and delayed my arrival by 6 hours.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

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.

Extremely disappointing. My original Denver–Vancouver–Bangkok itinerary was cancelled due to a crewing issue. I was not proactively supported and had to drive back home after already reaching the airport. Communication was poor throughout, and attempts to contact customer service resulted in being on hold for nearly three hours without reaching anyone. Instead of being rebooked on the same direct routing the following day, I was rerouted onto a much longer itinerary via multiple cities and airlines, which resulted in arriving approximately 30 hours later than scheduled. At Denver airport, there was no visible Air Canada representative available to properly assist. Ground staff offered no real support beyond directing passengers to a phone number. There was no clear communication, no ownership, and no meaningful customer care during a major disruption. The final journey involved three flights instead of the original two, significantly increasing travel time and stress. Overall, the handling of the cancellation and lack of customer support was unacceptable. What could have been better? Clear communication during the cancellation Accessible customer service (phone support that actually answers) Proper in-person assistance at the airport Rebooking onto a comparable routing rather than a significantly longer one

Great setup on both flights except the last flight we got condensed dripping all over me in the last 20 mins of the flight

The last 3 hours it was freezing cold in row 56. Multiple people had their winter coats on and were utilizing the blankets provided by the airline. I also did not have easy access to figure out how to book my food allergy and advance for my meals. Most of everything I received was something I couldn't eat. This needs to be made more accessible. Also, I'm 5'10 which is the average height of the American male. I flew from Philadelphia to Toronto and then to Tokyo and the seats were absolutely unbearable. For that long of a flight it is impossible to get comfortable when doing anything. Flights need to have more space and stop prioritizing costs over people.

Was delayed at every point/ connection. Luggages missing for 5days. Had no medications for diabetes and high B/p. when bags where finally delivered on the 30th, the insulin and ozempic were no longer patent, as the ice pack had since dissolved and the authenticity of the med is now questionable, since they must be refrigerated. Please have them refund my bag fees. I should sue them for all the inconveniences caused to me.

The plane was delayed substantially due to a mechanical problem, that being said, the airline was very fair with providing a meal coupon for us. I would rather arrive late on a mechanically sound plane than the alternative. The food served in the plane was just awful, however and I recommend a new catering company.

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

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

Information on your arrival and departure airports