$250 Find Cheap Flights from Chicago to Trinidad and Tobago - Compare and Save

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 9/19. 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.
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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$509
Port of Spain
Port of Spain1 stop$509

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

Thu, Sep 24 - Fri, Oct 2
Multiple Airlines Logo
7:11 am - 8:00 pmORD  Chicago O'Hare Intl-POS Port of Spain Piarco Intl
11h 49m1 stop Fort Lauderdale
Multiple Airlines Logo
10:10 am - 3:20 pmPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
30h 10m1 stop Fort Lauderdale
$509Multiple Airlines
Sat, Aug 22 - Sat, Aug 29
Multiple Airlines Logo
8:50 pm - 12:15 amORD  Chicago O'Hare Intl-POS Port of Spain Piarco Intl
26h 25m1 stop Toronto Pearson Intl
Multiple Airlines Logo
8:00 pm - 8:52 amPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
13h 52m1 stop New York John F Kennedy Intl
$527Multiple Airlines
Sat, Sep 19 - Fri, Sep 25
Air Canada Logo
3:45 pm - 12:15 amORD  Chicago O'Hare Intl-POS Port of Spain Piarco Intl
31h 30m1 stop Toronto Pearson Intl
Air Canada Logo
1:20 am - 2:55 pmPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
14h 35m1 stop Toronto Pearson Intl
$530Air Canada
Sat, Sep 19 - Fri, Sep 25
Air Canada Logo
8:40 pm - 12:15 amORD  Chicago O'Hare Intl-POS Port of Spain Piarco Intl
26h 35m1 stop Toronto Pearson Intl
Air Canada Logo
1:20 am - 8:12 pmPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
19h 52m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl
$534Air Canada
Thu, Sep 17 - Fri, Sep 25
Multiple Airlines Logo
7:11 am - 8:00 pmORD  Chicago O'Hare Intl-POS Port of Spain Piarco Intl
11h 49m1 stop Fort Lauderdale
Multiple Airlines Logo
10:10 am - 3:20 pmPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
30h 10m1 stop Fort Lauderdale
$536Multiple Airlines
Mon, Sep 14 - Tue, Sep 29
Copa Airlines Logo
3:20 pm - 1:47 amORD  Chicago O'Hare Intl-POS Port of Spain Piarco Intl
9h 27m1 stop Panama City Tocumen Intl
Copa Airlines Logo
3:50 am - 1:59 pmPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
11h 09m1 stop Panama City Tocumen Intl
$568Copa Airlines
Wed, Sep 23 - Sat, Sep 26
Copa Airlines Logo
8:01 am - 1:47 amORD  Chicago O'Hare Intl-POS Port of Spain Piarco Intl
16h 46m1 stop Panama City Tocumen Intl
Copa Airlines Logo
3:50 am - 1:59 pmPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
11h 09m1 stop Panama City Tocumen Intl
$568Copa Airlines
Sat, Sep 19 - Sat, Sep 26
American Airlines Logo
8:55 pm - 2:06 pmORD  Chicago O'Hare Intl-POS Port of Spain Piarco Intl
16h 11m2 stops Washington, D.C. Reagan-National Miami
American Airlines Logo
3:06 pm - 7:42 amPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
17h 36m2 stops Miami Dallas/Fort Worth
$572American Airlines
Thu, Sep 17 - Fri, Sep 25
American Airlines Logo
9:01 pm - 2:06 pmORD  Chicago O'Hare Intl-POS Port of Spain Piarco Intl
16h 05m2 stops Charlotte Douglas Miami
American Airlines Logo
3:06 pm - 7:58 amPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
17h 52m2 stops Miami Washington, D.C. Reagan-National
$584American Airlines
Thu, Aug 20 - Tue, Sep 29
United Airlines Logo
12:16 pm - 12:50 amORD  Chicago O'Hare Intl-POS Port of Spain Piarco Intl
11h 34m1 stop Newark
United Airlines Logo
12:30 am - 2:50 pmPOS  Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
15h 20m1 stop Houston George Bush Intcntl
$821United 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 February and April, when the average cost of round-trip tickets is $948 and $794 respectively.

Good to know

Low season

January

Cheapest flight

$250
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly with an average 38% 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.
7.6
Copa AirlinesOverall score based on 1563 reviews
6.8Entertainment
7.4Comfort
8.1Crew
7.8Boarding
6.9Food
Airline reviews

We where skipped for this flight will not head to Panama until tonight..

2.0 MediocreRussell, Jul 2026
Read more Copa Airlines reviews

We where skipped for this flight will not head to Panama until tonight..

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

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

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

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

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

Placed us in the last rear row of the plane so could not recline seats because of the rear wall, and also made it more of a tight space when the passenger in front reclined their seat. While understand seat assignments, every passenger should be afforded a reclining seat. The odor control scent from the restrooms was overwhelming strong. My wife and I could not deal with it, and she suffered a terrible headache as a result. I kept getting hit by the crew since I was on the ilse seat. No apologies, nothing. They made me feel like I was supposed to take the beating for a 3 hr flight.

Well the airline was fine. The only thing is I was charged for a checked in luggage. But when I reserved the ticket it showed a check in bag allowed. Who can I get in contact with for reimbursement.? The airline said I had to speak to whoever I booked ticket with.

Old 757 with poor entertainment system. United no longer partners with United for free text and email. O'Hara an absolute disaster! Limited gates clauses two hour delay. Unfortunately this appears to be the norm.

It was a good experience, unfortunately my checked baggages were come late and not arrived on time.

Very stressful to locate United Airline boarding area, delayed flight, changing boarding area again to another location with all tiredness 😩. But flying was fine.

It was hot and not as comfortable as the flight to Chicago. Must have been a different plane that needs to be worked on or replaced.

The SFO lounge closes at 12 midnight. My flight took off at 2AM

It was extremely hot in the cabin the entire flight, vent air was worn

Have not had a flight out or returning to Norfolk that has not required maintenance, and a gate delay. Properly staff the crew so maintenance can be performed without last minute emergencies on each flight and there is enough staff to have gates prepared for inbound flights. Staff to ensure the safety and on time service vs. profit.

We were forced to eat vegetarian food because non veg food ran out. The breakfast was mediocre.

My original flight was cancelled and that affected my trip and my plans and I got no compensation and customer service was hard to reach as well

The kid in the middle seat kicked me almost the whole flight, almost kicked my hot tea off my tray. The flight was delayed due to the first plane not being able to be de-iced in July! We had to get a new plane. Now I drive 3 hours back to Edmonton because direct flights from PVR were way to expensive

gate crew was courteous and helpful, flight attendant was nice and friendly once we got going. But we pushed off from the gate relatively on time, then sat there like 10 ft away, for an hour, with no announcement or explanation. Taxiing then took forever, and I get that there was runway congestion, but would be helpful to keep us posted on whats going on

The power outlets were not working for my row. Also felt like the seats have gotten smaller. I was in the window seat and felt like suffocated, as the two passengers next to me were tall and wide.

Terrible. The flight I booked had a convenient departure time. Quick layover. And an arrival timed that worked for the people who had to pick me up. Thanks to delays and rebooking I got none of those things

I had my flight of Cedar Rapids. THen Chicago to Boston. Flight out of Cedar rapids was delayed by 12 hrs. Had to drive to Chicago to catch my flight

Long delays to board due to mechanical issues with plane.

Flight was delayed, boarded, sat at the gate for more than 30 minutes, left the gate then waited on the pad for another 30 to 60 minutes then returned to the gate, deboarded and was cancelled... alternative flight was not booked automatically. Waited in line for 30 minutes but fortunately an alternate flight to a different destination was found ... no thanks to the travel agent used by kayak

The flight from Milwaukee to Dallas was great the staff absolutely amazing. After that EVERYTHING WENT DOWN HILL!!! ABSOLUTELY HORRIBLE!!! WILL NOT FLY THIS AIRLINE AGAIN

I was very unhappy with the lack of communication from the cockpit. It took close to a half an hour before we took off after the doors were closed, and we got no announcements as to progress. It would be nice to get some acknowledgement of the situation and updates as to when we are taking off.

The seat was not even cleaned. It has full of cookie crums probably from last flight's passenger. Its basic expectation that, seats are clean.

Very turbulent flight, no drinks, very little service, unorganized boarding, gate changed multiple times

The code sharing reservation with United was messed up requiring extra trip to airport to fix. Air Canada customer service 2.5 hours on hold and resolved nothing.

I'm 6'8" (2.03m) so more legroom would alwqys be appreciated, especially on long international flights. The food choices were underwhelming.

Didn’t make it on the flight. Delayed then had to be rebooked, which in turn had me waiting at the airport for another 8 hours before next flight

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)

Short flight. Everything was fine except the flight was delayed twice for a total of an hour.

There labor disputes cancelled my flight less than 24 hours before my boarding time but there customer service/website was easy enough to navigate and they rebooked me for no upcharge.

Very bad, flight was cancelled due to strike and staff was unable to rebook us

Flight was delayed by 1.5hrs. Once inside, people had their small handbags on the storage. The crew (male guy) was not helpful in making some space in the storage. Instead, he asked few bags to be checked-in and it was not a great experience. No attempt to help but just followed the things with a straight face. People had their literally small bags and he wouldnt not move from one storage to another even if there was space and would not let us do i as well. Once flight was on, they ran out of Orange juice, really running out of orange juice when the temp were 32.degrees outside. didnt made the sense. Onasking for a extra snack, he made a face as if he was giving me out of his pocket. if the flight was delayed, there could have an attempt to provide something extra incase people did asked.

Abandoned me in hallway in a wheelchair… which I asked for because I sprained my back. After waiting in the hallway, I decided to walk the rest of the way since someone respecting me up.. My experience with the united was totally the opposite. Wheelchair access, propped swift and save me a lot of grief. Air Canada totally disorganized.

Terrible confusion btw air Canada and United. Wasn’t able to change ticket because I had purchased on kayak. Rethinking booking tickets on this site, and will try to avoid United and aircanada going forward.

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

Information on your arrival and departure airports