$243 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 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

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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

Wed, Oct 15 - Sun, Oct 26
 Logo
9:10 am - 9:22 amPOS-ORD
25h 12m1 stop
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10:27 am - 4:15 amORD-POS
16h 48m1 stop
Wed, Oct 15 - Sun, Oct 26
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2:40 pm - 9:22 amPOS-ORD
19h 42m2 stops
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10:27 am - 4:15 amORD-POS
16h 48m1 stop
Wed, Sep 3 - Wed, Sep 10
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9:10 am - 1:12 pmPOS-ORD
29h 02m2 stops
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10:27 am - 6:55 pmORD-POS
31h 28m1 stop
Wed, Sep 3 - Wed, Sep 10
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9:10 am - 9:18 amPOS-ORD
25h 08m1 stop
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10:27 am - 6:55 pmORD-POS
31h 28m1 stop
Thu, Dec 11 - Sat, Jan 17
Copa Airlines Logo
3:47 am - 12:46 pmPOS-ORD
10h 59m1 stop
Copa Airlines Logo
2:13 pm - 1:44 amORD-POS
9h 31m1 stop
$562Copa Airlines
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Tue, Oct 14 - Sun, Oct 26
United Airlines Logo
12:30 am - 12:14 amPOS-ORD
24h 44m1 stop
United Airlines Logo
9:08 pm - 11:23 pmORD-POS
25h 15m1 stop
$575United Airlines
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Wed, Oct 15 - Sun, Oct 26
American Airlines Logo
7:00 am - 9:10 pmPOS-ORD
15h 10m2 stops
American Airlines Logo
8:45 am - 9:20 pmORD-POS
11h 35m2 stops
$578American Airlines
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Thu, Dec 11 - Sat, Jan 17
Air Canada Logo
2:15 am - 6:55 pmPOS-ORD
42h 40m2 stops
Air Canada Logo
3:55 pm - 1:10 amORD-POS
31h 15m1 stop
$584Air Canada
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Fri, Dec 12 - Sat, Jan 17
American Airlines Logo
7:10 am - 7:26 pmPOS-ORD
14h 16m2 stops
American Airlines Logo
8:05 am - 10:20 pmORD-POS
12h 15m2 stops
$691American Airlines
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Thu, Dec 11 - Sat, Jan 17
Air Canada Logo
2:15 am - 6:55 pmPOS-ORD
42h 40m2 stops
Air Canada Logo
9:30 pm - 1:10 amORD-POS
25h 40m2 stops
$921Air Canada
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Good to know

Low seasonJune
Cheapest flight$243
Best time to beat the crowds with an average 34% drop in price.
Most popular time to fly with an average 16% 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 airlines flying 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.
7.4
United AirlinesOverall score based on 8928 reviews
7.3Comfort
7.7Boarding
8.1Crew
7.1Entertainment
6.6Food
Airline reviews

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

2.0 MediocreAnonymous, Aug 2025RSW - ORD
Read more United Airlines reviews

Flight attendant in first class gave poor service (like he didn't want to be there) and food was awful. We sat waiting for gate upon arrival over 45 mins.

Inoperable monitor left no entert for 9 hours. Crew was not helpful Food was awful.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Overall it was good. I missed my connection but I was put on another flight.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

All flight attendants could benefit by taking an international flight on Qantas Airline. Qantas attendants are much more hospitable in every way. Much superior than and attendants on any US airline.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

Any flight to ORD after about 2pm this summer has been challenging. Flight was delayed getting in (coming from ORD) and that led to it not leaving before a ground stop due to lightening before they could fuel the plane, and so forth. They made up some time but we were still late in arriving at ORD, and that led to missed connections.

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

Worst flight ever. I was suppose to have a 3 1/2 hour layover in Chicago but got to the gate 4 minutes before boarding.

My flight got switched and my prepaid bag didnt transfer over properly so I paid to check ANOTHER BAG. I was placed in a middle seat and it was just miserable. At least it was a bulkhead row so I had legroom. The flight just never seem3d to end

They should have MSNBC available on board. A 4- hour flight should provide more than a cookie.

Was not able to watch most shows on the entertainment site. They would not load

On Wednesday, July 30 we were in mid flight from Manchester to Charlotte and we turned around because the right engine was malfunctioning. That was the last flight out of Manchester that night. I was rebooked for Thursday, which became a weather event Friday. There were no seats left on the flight from Manchester to Charlotte. Consequently I didn’t leave Manchester until Saturday morning and we flew to Chicago so to say the least my scheduled flight and return to Iowa was three days off and it messed with my business schedule. Consequently cash flow. I would like some sort of acknowledgment of this event.

Dreadful experience. Our flight was delayed more than 8 hours due to a maintenance issue and the assistance from rebooking was poor. I was travelling with a bad knee and needed assistance waited in one place more than 3 hours before someone came with a wheelchair. The woman next to me was a 91 year old great grandmother who had waited more than 4 hours. There were moments of support from the staff but it appeared as they were going against the direction of management. It was apathy, lack of ownership and dismissive responses with small moments of kindness and understanding typically from grey haired, female, veteran staff..

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

Traveling to a place near Chicago?

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