$189 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 9/15. 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

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

Cheap Flights from Chicago to Trinidad

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Port of Spain
Port of Spain1 stop$408
Port of Spain
Port of Spain1 stop$408

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

Thu, Sep 18 - Sun, Sep 21
 Logo
10:27 am - 4:15 amORD-POS
16h 48m1 stop
 Logo
6:25 pm - 9:18 amPOS-ORD
15h 53m1 stop
Thu, Sep 18 - Sun, Sep 21
 Logo
10:27 am - 4:15 amORD-POS
16h 48m1 stop
 Logo
6:25 pm - 9:18 amPOS-ORD
15h 53m1 stop
Sun, Oct 5 - Fri, Oct 24
Air Canada Logo
8:40 am - 1:20 amORD-POS
15h 40m2 stops
Air Canada Logo
2:25 am - 2:55 pmPOS-ORD
13h 30m2 stops
$523Air Canada
Find Deal
Fri, Sep 19 - Sun, Sep 28
Air Canada Logo
10:40 am - 1:20 amORD-POS
13h 40m2 stops
Air Canada Logo
2:25 am - 6:54 pmPOS-ORD
17h 29m2 stops
$528Air Canada
Find Deal
Thu, Sep 11 - Tue, Sep 23
American Airlines Logo
7:25 pm - 2:16 pmORD-POS
17h 51m1 stop
American Airlines Logo
3:25 pm - 11:49 pmPOS-ORD
9h 24m1 stop
$549American Airlines
Find Deal
Thu, Sep 11 - Tue, Sep 23
American Airlines Logo
8:30 pm - 2:16 pmORD-POS
16h 46m2 stops
American Airlines Logo
3:25 pm - 9:26 amPOS-ORD
19h 01m2 stops
$553American Airlines
Find Deal
Wed, Oct 22 - Sat, Oct 25
Copa Airlines Logo
7:53 am - 1:46 amORD-POS
16h 53m1 stop
Copa Airlines Logo
3:51 am - 1:41 pmPOS-ORD
10h 50m1 stop
$594Copa Airlines
Find Deal
Sun, Feb 8 - Sat, Feb 14
United Airlines Logo
12:45 pm - 1:05 amORD-POS
10h 20m1 stop
United Airlines Logo
1:30 am - 10:07 amPOS-ORD
10h 37m1 stop
$650United Airlines
Find Deal
Wed, Oct 22 - Sat, Oct 25
United Airlines Logo
7:10 am - 11:23 pmORD-POS
15h 13m1 stop
United Airlines Logo
12:30 am - 10:02 amPOS-ORD
10h 32m1 stop
$658United Airlines
Find Deal
Mon, Feb 9 - Fri, Feb 13
Copa Airlines Logo
6:56 am - 1:44 amORD-POS
16h 48m1 stop
Copa Airlines Logo
2:33 pm - 12:04 amPOS-ORD
11h 31m1 stop
$845Copa Airlines
Find Deal
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 $1,028, 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 January, when tickets cost $528 (return) on average. On the other hand, the most expensive months are December and April, when the average cost of round-trip tickets is $844 and $722 respectively.

What’s the cheapest day of the week to fly from Chicago to Trinidad?

The average price of all round-trip flights from Chicago O'Hare Intl Airport to Trinidad clicked on KAYAK for each day over the last 12 months.

When flying from Chicago to Trinidad, you should consider leaving on a Sunday and avoid Mondays if you are looking for the best rates. For your return to Chicago, you’ll find the best rates on Thursdays and the most expensive ones on Wednesdays.

Good to know

Low seasonSeptember
Cheapest flight$189
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly and prices are also 1% lower on average.
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.

  • What is the cheapest time of day to fly to Trinidad?

    The cheapest time of day to fly to Trinidad 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 is generally at night, which is peak travel time and where the average cost of a ticket is $905.

Reviews of the top airlines flying 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 8928 reviews
7.1Entertainment
7.3Comfort
8.1Crew
6.6Food
7.7Boarding
Airline reviews

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

10.0 ExcellentDr. Joseph, Aug 2025ORD - DEN
Read more United Airlines reviews

Excellent flight. Boarding was efficient and departure was on time. Smooth flight with on time arrival. Deplaning was also efficient.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

It was great, I’m very grateful for the pilots and crew flight attendants for everything.

Evidently, my seat had the only broken TV. I couldn’t plug it in, get it to come on, or watch anything, and of course, no one could fix it while we were on the plane. The service was good and the boarding was quick

The boarding of took of late.The presentation of the food was horrable as was the tast of the food was cold and tastless.

Delay and keep changing gates. I have to run around from B to C then to E.

I was charged for my daughters bag when I am supposed to receive two free checked bags with my United Explorer card.

The schedule to Moline changed 5 times. The gate changed 6 times. That is a pathetic way to run an airline. No wonder that no one in our company flies on United Express to or from Moline. Changes happen most of the time. I learned my lesson on this trip…never again!

Flight was great. Efficient boarding. Short flight. Early arrival. Friendly flight crew. The entertainment system did not work well. Could not access it until the aircraft reached 10K feet or more. Lots of glitches.

A bit rush for transit. Food and entertainment are not available

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

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

Excellent! The gate agents were kind enough to rebook me on an earlier flight saving me from a 6 hour layover. Even my luggage made it despite the fact that the connection was technically too narrow. The flight itself was very comfortable, roomy, and clean. Plenty of space for my carryon items with plugs to charge my phone. After a long international flight of 14 hours, this was an excellent way to end my travels!

Great experience. Flight boarded easily. Departed early. Smooth flight. Great arrival in DC--almost no taxing! Almost direct to gate from runway. Crew was terrific. Same cookies and beverages in main cabin. I did not use the entertainment system on this flight.

This particular flight wasn't very full at the back, so there were three seats available for spreading out and getting relatively comfortable

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

Everything you need to know for your flight to Trinidad

Information on your arrival and departure airports

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