$310 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 7/6. 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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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

Fri, Jul 11 - Sun, Jul 13
 Logo
11:10 am - 12:22 amPOS-ORD
14h 12m2 stops
 Logo
8:09 am - 4:15 amORD-POS
19h 06m1 stop
Tue, Aug 12 - Fri, Sep 12
United Airlines Logo
12:30 am - 11:11 amPOS-ORD
11h 41m1 stop
United Airlines Logo
4:50 pm - 11:23 pmORD-POS
29h 33m1 stop
$571United Airlines
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Mon, Sep 1 - Sat, Sep 27
Air Canada Logo
2:25 am - 5:33 pmPOS-ORD
16h 08m1 stop
Air Canada Logo
6:06 pm - 1:25 amORD-POS
30h 19m2 stops
$573Air Canada
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Wed, Sep 3 - Mon, Sep 29
American Airlines Logo
3:23 pm - 7:25 amPOS-ORD
17h 02m2 stops
American Airlines Logo
9:37 pm - 2:16 pmORD-POS
15h 39m2 stops
$578American Airlines
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Thu, Jul 10 - Tue, Jul 15
JetBlue Logo
8:50 am - 10:28 pmPOS-ORD
14h 38m1 stop
JetBlue Logo
6:16 am - 6:19 pmORD-POS
11h 03m1 stop
$596JetBlue
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Sun, Jul 6 - Mon, Aug 18
Air Canada Logo
2:20 am - 6:53 pmPOS-ORD
17h 33m2 stops
Air Canada Logo
2:00 pm - 1:20 amORD-POS
10h 20m1 stop
$605Air Canada
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Thu, Jul 10 - Sun, Jul 13
American Airlines Logo
3:05 pm - 12:17 amPOS-ORD
10h 12m1 stop
American Airlines Logo
5:00 am - 9:44 pmORD-POS
15h 44m1 stop
$664American Airlines
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Fri, Jul 11 - Sun, Jul 13
Copa Airlines Logo
2:35 pm - 12:20 amPOS-ORD
10h 45m1 stop
Copa Airlines Logo
7:54 am - 1:47 amORD-POS
16h 53m1 stop
$675Copa Airlines
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Thu, Jul 10 - Sun, Jul 13
Copa Airlines Logo
3:48 am - 1:42 pmPOS-ORD
10h 54m1 stop
Copa Airlines Logo
7:54 am - 1:47 amORD-POS
16h 53m1 stop
$733Copa Airlines
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Fri, Jul 11 - Sun, Jul 13
JetBlue Logo
7:29 pm - 11:18 amPOS-ORD
16h 49m1 stop
JetBlue Logo
6:16 am - 6:04 pmORD-POS
10h 48m1 stop
$905JetBlue
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Good to know

Low seasonFebruary
High seasonJuly
Cheapest flight$310
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly with an average 21% 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 8810 reviews
7.3Comfort
8.1Crew
6.6Food
7.0Entertainment
7.7Boarding
Airline reviews

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.

6.0 GoodAnonymous, Jun 2025MLI - ORD
Read more United Airlines reviews

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.

So far so good but food and entertainment are not available for this flight

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Overall poor for me I paid extra for seats with leg room and my regional flights exit row seats have less leg room then the others that's money that could have been saved and on my final flight home the flights air was not operating it was unbearably hot in the cabin I will be contacting United and filing a DOT complaint

It was my first time with United Airlines and I would say it was very good experience and best of all the flights were on time. Will definitely fly with United Airlines next time.

Very modern plane. Good seat spacing. Meals were good. Screens had tons of movies and worked

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

The flight was 2 hour delayed, otherwise everything was excellent. The delay was due to the hourly limit requirement so given that as a reason, I'm happy with the flight!

Not sure the logic of the boarding in Groups. I was loaded first on the aisle. Then the guy in the middle. Then the guy by the window. Constantly holding up the other people boarding behind them with us blocking the aisle and this happened in most of the other rows

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything was great. Boarding, early departure, early arrival, and deplaning were smooth. Smooth flight.

Per usual, flight status, staff courtesy and professionalism were excellent

The only thing is if Wi-Fi is available after you land and taxi to the gate. It takes forever to get to the gate, and having the Wi-Fi continue would be great to bide the time at least 5 minutes before you arrive at the entrance. That is my only comment; otherwise, everything was good.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

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