$260 Find Cheap Flights from Trinidad to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 3/24. 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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Everything you should know

Cheapest round-trip
$420
Typical prices: $579-$618
Multiple Airlines
Tue 1/13Tue 1/20
POS - ORD • 1 stop
Cheapest one-way
$260
Air Canada
Tue 3/24
POS - ORD • 2 stops
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Flight Deals
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Flight Deals

Cheap Flights from Trinidad to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Trinidad to Chicago 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 Trinidad to Chicago

Tue, Jan 13 - Tue, Jan 20
Multiple Airlines Logo
9:10 am - 8:18 amPOS-ORD
25h 08m1 stop
Multiple Airlines Logo
9:23 am - 6:55 pmORD-POS
31h 32m1 stop
$420Multiple Airlines
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Tue, Jan 13 - Tue, Jan 20
Multiple Airlines Logo
9:10 am - 8:18 amPOS-ORD
25h 08m1 stop
Multiple Airlines Logo
2:53 pm - 6:55 pmORD-POS
26h 02m2 stops
$452Multiple Airlines
Find Deal
Thu, Jan 15 - Mon, Jan 19
Air Canada Logo
2:20 am - 6:55 pmPOS-ORD
18h 35m2 stops
Air Canada Logo
6:00 pm - 1:20 amORD-POS
29h 20m2 stops
$471Air Canada
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Sun, Jan 11 - Sun, Jan 18
Multiple Airlines Logo
9:10 am - 8:18 amPOS-ORD
25h 08m1 stop
Multiple Airlines Logo
7:20 am - 8:00 pmORD-POS
10h 40m1 stop
$526Multiple Airlines
Find Deal
Sun, Jan 11 - Sun, Jan 18
Multiple Airlines Logo
9:10 am - 8:18 amPOS-ORD
25h 08m1 stop
Multiple Airlines Logo
8:51 pm - 8:00 pmORD-POS
21h 09m2 stops
$534Multiple Airlines
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Tue, Jan 13 - Tue, Jan 20
Multiple Airlines Logo
9:10 am - 1:13 pmPOS-ORD
30h 03m3 stops
Multiple Airlines Logo
10:00 am - 1:20 amORD-POS
13h 20m1 stop
$541Multiple Airlines
Find Deal
Mon, Jan 12 - Tue, Jan 20
Copa Airlines Logo
3:40 am - 12:46 pmPOS-ORD
11h 06m1 stop
Copa Airlines Logo
2:13 pm - 1:44 amORD-POS
9h 31m1 stop
$562Copa Airlines
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Mon, Jan 12 - Tue, Jan 20
Multiple Airlines Logo
12:10 am - 4:52 pmPOS-ORD
18h 42m2 stops
Multiple Airlines Logo
9:23 am - 6:55 pmORD-POS
31h 32m1 stop
$565Multiple Airlines
Find Deal
Wed, May 6 - Sun, May 10
Copa Airlines Logo
2:22 pm - 1:15 amPOS-ORD
11h 53m1 stop
Copa Airlines Logo
3:21 pm - 1:46 amORD-POS
9h 25m1 stop
$583Copa Airlines
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Sun, Jan 11 - Sun, Jan 18
Multiple Airlines Logo
9:10 am - 9:03 pmPOS-ORD
37h 53m3 stops
Multiple Airlines Logo
5:15 am - 8:00 pmORD-POS
12h 45m1 stop
$587Multiple Airlines
Find Deal
Useful Info

Good to know

Low seasonJune
Cheapest flight$260
Best time to beat the crowds with an average 34% drop in price.
Most popular time to fly with an average 5% increase in price.
Flight from Port of Spain to Chicago

FAQs for booking Trinidad to Chicago flights

  • How does KAYAK find such low prices on flights from Trinidad to Chicago?

    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 Trinidad to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Trinidad to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from 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 Trinidad to Chicago?

    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 to Chicago with an airline and back to Trinidad with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Trinidad to Chicago?

    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 to Chicago from Trinidad up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 3 airlines serving from Trinidad to Chicago

 
Need help choosing which airline to fly with from Trinidad to Chicago? 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 1566 reviews
8.1Crew
7.8Boarding
6.9Food
6.8Entertainment
7.4Comfort
Airline reviews

I always enjoy flying Copa. There are very few airlines where I can enjoy a comfortable sleep in-flight. The snacks weren't the best, but they sufficed. The in-flight entertainment was fantastic, and I crossed another movie off my watch list.

8.0 ExcellentTisagh, Nov 2025SDQ - PTY
Read more Copa Airlines reviews

I always enjoy flying Copa. There are very few airlines where I can enjoy a comfortable sleep in-flight. The snacks weren't the best, but they sufficed. The in-flight entertainment was fantastic, and I crossed another movie off my watch list.

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.

We had a great flight just wished they had a tv so we can see a movie that would of made my trip excellent.

horrible service, food was an embarrassment, no charging for cellphones, stay away

Great experience with a crew always thinking in the passenger

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

Had to go through security at the gate again. Had to take off shoes and go through the whole thing again even though we have global entry. They asked us to check in items bought at duty free during our layover and since we checked our luggage at the original departure airport, they forced us to check in a small backpack. None of this ever happened with other airlines. In addition, no vegetarian food option and no snacks during a 7 hr flight. Luggage limits are unusually small. This is unacceptable. Will NEVER fly Copa again and will tell friends and family to avoid this airline.

We paid extra with copa for seats near one another The plane was changed and we lost our seats We were all Separated. We have not received a refund for our seats despite emailing and calling.

Tell people to remain in their seats during the meal/beverage distribution. Enforce boarding by group numbers. No one was checking. Tell people to turn their electronics speakers off. Bigger cups for drinks.

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

United has come a long way, it’s been a fantastic experience traveling with them.

This flight leg was fantastic - super comfortable and a great selection of things to watch on the TV. Staff were excellent, really above and beyond.

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Excellent all round, first time flying United. App is very helpful.

Efficient all round, very good crew. Short flight so the food, of course, was just snacks

Better WiFi. I cannot understand that in 2025, United is so behind on a technology that is now a necessity and still painfully unreliable, slow and keeps disconnecting.

Trip was great. A wild landing in Ottawa with the wind and rain, but the pilot did a great job. Always love flying United.👍

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

It was a typical flight. We had a delay which seems to be the normality now. And we had no in flight service due to conditions.

After we landed we sat on the tarmac for 1.5 hours waiting to get to our gate. Ridiculous.

Flight, food and crew were all good, friendly and very satisfactory.

Terrible. Flight delayed for more than 8 hours with only a $12 meal voucher provided for the inconvenience. The airplane did not have breaks on arrival yet they still made us go through the motions and board on time knowing we could not take off then sit for 40+ minutes before having to get of the time. A complete waste of my time. I cannot believe they can stay business with these shenanigans. I’ll avoid this company like the plague moving forward as the lack of accountability is disgraceful.

This was the best 2 flights I have had with American out of SGF. Great crew both flights.

Premium economy seat was decent. As always poor headphones, poor food and beverage, crew is not overly friendly

Excellent - explanations were clear staff was nice and flight was comfortable

Lost bag and 2 days no word leaving for cruise no clothes or stuff

Traveling to a place near Chicago?

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