$208 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 7/17. 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.
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1 adult, Economy

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Best Trinidad and Tobago Flight Deals from Chicago

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Port of Spain
Port of Spain1 stop$495
Port of Spain
Port of Spain1 stop$495

Cheap Flights from Chicago to Trinidad and Tobago

 
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

Mon, Oct 6 - Wed, Oct 8
 Logo
3:11 pm - 6:55 pmORD-POS
26h 44m1 stop
 Logo
9:10 am - 10:47 pmPOS-ORD
14h 37m1 stop
Thu, Jul 10 - Mon, Jul 14
Copa Airlines Logo
7:54 am - 1:47 amORD-POS
16h 53m1 stop
Copa Airlines Logo
2:35 pm - 12:20 amPOS-ORD
10h 45m1 stop
$502Copa Airlines
Find Deal
Mon, Jul 14 - Mon, Jul 21
Air Canada Logo
10:40 am - 1:20 amORD-POS
13h 40m2 stops
Air Canada Logo
2:20 am - 6:53 pmPOS-ORD
17h 33m2 stops
$517Air Canada
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Mon, Jul 14 - Mon, Jul 21
Air Canada Logo
10:40 am - 1:20 amORD-POS
13h 40m2 stops
Air Canada Logo
2:20 am - 6:53 pmPOS-ORD
17h 33m2 stops
$527Air Canada
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Fri, Sep 12 - Fri, Sep 19
American Airlines Logo
7:15 pm - 2:16 pmORD-POS
18h 01m1 stop
American Airlines Logo
3:23 pm - 8:45 amPOS-ORD
18h 22m1 stop
$548American Airlines
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Mon, Oct 6 - Wed, Oct 8
American Airlines Logo
7:00 am - 9:25 pmORD-POS
13h 25m2 stops
American Airlines Logo
8:00 am - 9:25 pmPOS-ORD
14h 25m2 stops
$553American Airlines
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Mon, Oct 6 - Tue, Oct 7
United Airlines Logo
9:00 am - 11:23 pmORD-POS
13h 23m1 stop
United Airlines Logo
12:30 am - 11:05 amPOS-ORD
11h 35m1 stop
$648United Airlines
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Sun, Jul 6 - Tue, Jul 8
United Airlines Logo
9:50 pm - 11:23 pmORD-POS
24h 33m1 stop
United Airlines Logo
12:30 am - 10:21 amPOS-ORD
10h 51m1 stop
$659United Airlines
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Thu, Aug 14 - Wed, Aug 27
JetBlue Logo
6:00 am - 6:24 pmORD-POS
11h 24m1 stop
JetBlue Logo
9:22 am - 10:28 pmPOS-ORD
14h 06m1 stop
$688JetBlue
Find Deal
Fri, Aug 1 - Fri, Aug 8
JetBlue Logo
6:16 am - 6:04 pmORD-POS
10h 48m1 stop
JetBlue Logo
7:29 pm - 10:20 amPOS-ORD
15h 51m1 stop
$851JetBlue
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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 June, when tickets cost $526 (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 $777 respectively.

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

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

If you are looking for a flight deal from Chicago to Trinidad and Tobago, look for departures on Sundays and avoid leaving on a Monday, as it's usually the priciest day. When flying back from Trinidad and Tobago, Thursday is the cheapest day to fly and Wednesday is the most expensive.


Good to know

Low seasonJune
High seasonFebruary
Cheapest flight$208
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly and prices are also 0% lower on average.
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 airlines flying 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 8809 reviews
7.0Entertainment
8.1Crew
7.7Boarding
6.6Food
7.3Comfort
Airline reviews

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

8.0 ExcellentStacie, Jun 2025ORD - ALB
Read more United Airlines reviews

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

Boarding was a little difficult. The gate area at O'Hare was very small and crowded due to multiple gates in the area. Could not hear the intercom, so had to rely on signage to see when my group was boarding and the signage was blocked by passengers standing in the gate. Flight was great and we arrived in Montreal on time.

Smooth boarding process. Early departure, smooth flight, early arrival. The entertainment package has very good recent movie options. The flight crew were friendly and professional.

I do prefer to fly United and have always had excellent service, except for bad weather. Flights are on time and staff is alway curtious and helpful

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.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

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

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