- Argentina (Español)
- Australia (English)
- Österreich (Deutsch)
- Belgique (Français)
- België (Nederlands)
- Bolivia (Español)
- Brasil (Português)
- Canada (English)
- Canada (Français)
- Chile (Español)
- Colombia (Español)
- Costa Rica (Español)
- Česká republika (Čeština)
- Danmark (Dansk)
- Deutschland (Deutsch)
- Germany (English)
- Ecuador (Español)
- El Salvador (Español)
- España (Español)
- Espanya (Català)
- France (Français)
- Ελλάδα (Ελληνική)
- Guatemala (Español)
- Honduras (Español)
- Hong Kong (English)
- 香港 (中文)
- India (English)
- Indonesia (Bahasa Indonesia)
- Indonesia (English)
- Ireland (English)
- Israel (English)
- ישראל (עִבְרִית)
- Italia (Italiano)
- 日本 (日本語)
- Malaysia (English)
- Malaysia (Melayu)
- México (Español)
- Nederland (Nederlands)
- New Zealand (English)
- Nicaragua (Español)
- Norge (Norsk)
- Panamá (Español)
- Paraguay (Español)
- Perú (Español)
- Philippines (English)
- Polska (Polski)
- Portugal (Português)
- Puerto Rico (Español)
- República Dominicana (Español)
- România (Română)
- المملكة العربية السعودية (العَرَبِيَّة)
- Saudi Arabia (English)
- Suisse (Français)
- Schweiz (Deutsch)
- Singapore (English)
- South Africa (English)
- 대한민국 (한국어)
- Suomi (Suomi)
- Sverige (Svenska)
- 台灣 (中文)
- ประเทศไทย (ภาษาไทย)
- Thailand (English)
- Türkiye (Türkçe)
- Україна (Українська)
- United Arab Emirates (English)
- United Kingdom (English)
- United States (English)
- Estados Unidos (Español)
- Uruguay (Español)
- Venezuela (Español)
- Vietnam (English)
- Việt Nam (Việt)

Flight Deals
Cheap Flights from Chicago to Trinidad and Tobago
Cheapest round-trip prices found by our users on KAYAK in the last 5 daysBook 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, Apr 15 - Fri, Apr 23
3:13 pm - 1:57 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl
21h 44m1 stop Panama City Tocumen Intl
3:39 am - 12:44 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
22h 05m1 stop Panama City Tocumen Intl
$648Copa Airlines
Tue, Dec 1 - Mon, Dec 7
2:13 pm - 1:27 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl
21h 14m1 stop Panama City Tocumen Intl
3:23 am - 12:46 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
11h 23m1 stop Panama City Tocumen Intl
$648Copa Airlines
Tue, Dec 1 - Mon, Dec 21
2:13 pm - 1:27 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl
21h 14m1 stop Panama City Tocumen Intl
3:23 am - 12:46 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
11h 23m1 stop Panama City Tocumen Intl
$648Copa Airlines
Sat, Dec 5 - Sat, Dec 12
7:50 pm - 3:35 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl
17h 45m1 stop Miami
4:42 pm - 9:30 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
18h 48m1 stop Miami
$660American Airlines
Thu, Dec 3 - Fri, Dec 11
7:50 pm - 3:35 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl
17h 45m1 stop Miami
5:56 am - 3:44 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
11h 48m1 stop Miami
$660American Airlines
Sat, Dec 5 - Sat, Dec 12
7:50 pm - 3:35 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl
17h 45m1 stop Miami
5:56 am - 8:11 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
16h 15m2 stops Miami Charlotte Douglas
$665American Airlines
Thu, Dec 3 - Thu, Dec 10
7:05 am - 1:00 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl
15h 55m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
2:15 am - 3:02 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
14h 47m2 stops Toronto Pearson Intl Montreal Pierre Elliott Trudeau Intl
$692Air Canada
Thu, Dec 3 - Fri, Dec 11
10:05 am - 1:00 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl
12h 55m1 stop Toronto Pearson Intl
2:15 am - 1:13 pmPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
12h 58m1 stop Toronto Pearson Intl
$694Air Canada
Sun, Nov 8 - Sat, Nov 14
7:29 am - 12:18 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl
14h 49m1 stop Houston George Bush Intcntl
1:25 am - 10:11 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
10h 46m1 stop Houston George Bush Intcntl
$705United Airlines
Tue, Nov 10 - Sun, Nov 22
12:40 pm - 12:18 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl
9h 38m1 stop Houston George Bush Intcntl
1:25 am - 11:17 amPOS Port of Spain Piarco Intl-ORD Chicago O'Hare Intl
11h 52m1 stop Houston George Bush Intcntl
$705United Airlines
Recent one-way flight deals from Chicago to Trinidad and Tobago
Tue, Nov 10
9:51 am - 1:54 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl
38h 03m3 stops Orlando San Juan Luis Munoz Marin Intl Panama City Tocumen Intl
$323Multiple Airlines
Tue, Nov 10
9:51 am - 1:17 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl
25h 26m3 stops Orlando San Juan Luis Munoz Marin Intl Panama City Tocumen Intl
$340Multiple Airlines
Mon, Nov 9
7:55 am - 8:00 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl
10h 05m1 stop Fort Lauderdale
$344Multiple Airlines
Tue, Dec 8
9:53 am - 11:40 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl
11h 47m2 stops Washington, D.C. Reagan-National Miami
$349American Airlines
Tue, Dec 8
6:50 am - 12:18 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl
15h 28m1 stop Houston George Bush Intcntl
$349United Airlines
Thu, Jan 21
4:30 pm - 1:00 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl
30h 30m1 stop Toronto Pearson Intl
$349Air Canada
Tue, Nov 10
3:40 pm - 1:00 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl
55h 20m2 stops Montreal Pierre Elliott Trudeau Intl Toronto Pearson Intl
$352Air Canada
Tue, Nov 10
5:00 am - 3:37 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl
8h 37m1 stop Miami
$423American Airlines
Wed, Nov 11
9:06 pm - 3:37 pmORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl
16h 31m2 stops Dallas/Fort Worth Miami
$431American Airlines
Wed, Nov 11
6:55 am - 12:18 amORD Chicago O'Hare Intl-POS Port of Spain Piarco Intl
15h 23m1 stop Houston George Bush Intcntl
$486United Airlines
Booking Insights
Price, demand and travel trends for Chicago O'Hare Intl Airport to Trinidad and Tobago flights
Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.
Prices
Airlines
More
What are the cheapest fares from Chicago O'Hare Intl Airport to Trinidad and Tobago right now?
The cheapest fare from Chicago O'Hare Intl Airport to Trinidad and Tobago in the last week was $648 round-trip, to Port of Spain Piarco Intl (POS).
Which airport in Trinidad and Tobago is the cheapest to fly to from Chicago O'Hare Intl Airport?
All flights from Chicago O'Hare Intl Airport to Trinidad and Tobago arrive at Port of Spain Piarco Intl (POS). On average, round-trip fares are around $660.
What’s the cheapest day to fly from Chicago O'Hare Intl Airport to Trinidad and Tobago?
Friday tends to be the cheapest day to fly from Chicago O'Hare Intl Airport to Trinidad and Tobago, while Monday is the most expensive. Fares run about 24% higher that day, based on the past 12 months of KAYAK data.
What's the cheapest time of day to fly from Chicago O'Hare Intl Airport to Trinidad and Tobago?
Data from the past 12 months shows it's cheapest to fly to Trinidad and Tobago during the evening with average prices of $607. The night is the most expensive time to fly, with average prices of $817.
What are the cheapest airlines to fly with from Chicago O'Hare Intl Airport to Trinidad and Tobago?
Fares reflect aggregated pricing data and may not include every trip type.
Looking at KAYAK data from the last 12 months, the cheapest airlines to fly with from Chicago O'Hare Intl Airport to Trinidad and Tobago are:
• Air Canada from $317
• American Airlines from $396
• United Airlines from $548
• Copa Airlines from $567
• JetBlue from $584
What's the most popular airline to fly with from Chicago O'Hare Intl Airport to Trinidad and Tobago?
Drawing on KAYAK data from the past three months, the most popular airlines to fly with from Chicago O'Hare Intl Airport to Trinidad and Tobago are:
• American Airlines
• United Airlines
• Copa Airlines
• Air Canada
What are the most popular flight destinations in Trinidad and Tobago?
Port of Spain is the most popular flight destination in Trinidad and Tobago, based on KAYAK data from the past 3 months.
Key details for Chicago O'Hare Intl Airport to Trinidad and Tobago flights
Low season | October |
|---|---|
High season | July |
Cheapest flight | $323 |
Your Chicago O'Hare Intl Airport to Trinidad and Tobago flight questions, answered
Find helpful answers about this route, including flight times, airports, airlines and booking tips.
Your guide to booking Chicago O'Hare Intl Airport to Trinidad and Tobago flights
Get tips on when to book, when to fly and what to know before your trip.Reviews of the top 3 airlines serving from Chicago to Trinidad and Tobago
7.3
United AirlinesOverall score based on 10397 reviews
7.1Entertainment
8.1Crew
6.7Food
7.7Boarding
7.3Comfort
Airline reviews
The TVs on the plane were all broken and inoperable. No snacks or food were served. Plane was very old and uncomfortable.
4.0 OkayJonathan, Oct 2026
The TVs on the plane were all broken and inoperable. No snacks or food were served. Plane was very old and uncomfortable.
Takeoff delayed 2 hrs. Boarded on time to find we were missing part of the flight crew. Then informed that they had loaded too much fuel. Spent 1 1/2 hrs sitting there burning off the excess, which included a couple of laps around the runway until we were light enough to fly! Ridiculous!
I especially enjoyed having a lightly packed flight which enabled me and my wife to occupy a three seat area with nobody in the middle seat.
The seats are very small, that is all the staff did a good job.
It was great. The staff is always helpful and polite. The app is great and makes the whole trip and process so easy. They even offer a step to step guide to your correct terminal. And they keep all the information you'll need updated. Anything you can think of! Great experience.
Perfect. On time and the weather was perfect so we came in a few minutes early.
On time. Carry on and personal bag was accommodated on the plane. Entertainment was accessible without bringing own device. Whole can of juice was provided rather than a pour.
Price was crazy watch it if you Chan he your flight
On time, easy boarding. Anytime you sit in an economy seat, it’s uncomfortable. New plane and the bathrooms were in the galley at the back of the plane which seemed odd.
Terrible service - they don’t want to be there and bad food. Entertainment system in economy from the 2000s
Wonderful experience. Long distance travel is never easy but this flight was a treat. Flight crew was very attentive and friendly
Same as my Tulsa to Chicago flight, this one was quick and professional.
Boarding was delayed 50 minutes. The flight going to Chicago was canceled, causing lots of problems and causing me to rebook and miss an event. I was traveling with a colleague, and he was unable to get on the same flight after 40 minutes on the phone, which meant I had to wait for him after my arrival. My flight down was delayed an hour before take off, had to sit on the plane, then 30 minutes after landing to get to a gate. No real food, only juice/ water offered for the 3.5 hours on the plane. Not a good experience.
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
Crew were helpful, pilot kept us informed about turbulence, snack choice was awesome!
It was one of the worst I have ever had. The plane was over booked, and I did not have a seat. When I questioned why because I had booked this weeks in advance. I was brushed off to be advised they are trying to find someone to give up their seat. Only to be advised I would be boarding last. I had priority boarding in group 1-4. When I asked why I had to be last because that is not what I paid for I was advised it doesn't matter you will get a seat. The ticket person was very rude and unprofessional. The gate changed several times and it was going from one area to another area far away from where we were at. I feel like I should have been compensated in some kind of way because of the way I was treated. The ticket agent acted like it was my fault that the plane was over booked. Not one time was I apologized to for this inconvenience.
We did not fly on American Airlines from Chicago to London. We were rebooked on British Airways (by American Airlines) and our luggage was left behind. A full day delay and lost luggage.
I have posted the comments in the first flight leg.
First class snacks - stewardess gave out multiples to everyone until there was almost no selection left when she got back to me last in first class cabin. Nothing left that I would eat.
My feedback from the trip to Columbia to Chicago was meant for Chicago to Denver.
The WiFi was out gr entire flight. Had to Diane for almost 1 hour to wait for a gate to open up for plane to dock. Very bad experience.
After boarding, the AC was shut off on the flight. At business class, I really could not breathe. I was absolutely dripping sweat. I was told by the FA that there was nothing they could do but I could stand by the door until departure. So, that's what I did. I was clearly in the way while the FAs were trying to do their work, but I had to be able to breathe. After that, of course, I had sweated up a lot so was very uncomfortable for the six hour flight.
DELAYED AGAIN and AGAIN and AGAIN - not only that, you delay in 20 minute increments for hours and hours instead of having an accurate delay understanding.
AA was fine....the overall experience was subpar, but not due to the airline due to broader issues
More options for your flight from Chicago to Trinidad and Tobago
Complete your trip to Trinidad and Tobago with a hotel stay or car rental
Information on your arrival and departure airports
Cabin class types available on flights to Trinidad and Tobago
Cabin classes available on flights to Trinidad and Tobago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
Flights from domestic origins to Trinidad and Tobago
Flights from all regions of Chicago to Trinidad and Tobago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
Flights to other popular destinations
The most popular flights on KAYAK according to clicks in the last 2 weeks. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.