$183 Find Cheap Flights from Trinidad and Tobago 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 5/8. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago O'Hare Intl Airport

 
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Trinidad and Tobago to Chicago

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

Wed, May 27 - Tue, Jun 23
Air Canada Logo
1:25 am - 1:25 pm
POS
-
ORD
13h 00m
1 stop
Air Canada Logo
8:40 pm - 12:15 am
ORD
-
POS
26h 35m
1 stop
$318Air Canada
Wed, May 27 - Thu, Jun 18
Air Canada Logo
1:25 am - 6:47 pm
POS
-
ORD
18h 22m
2 stops
Air Canada Logo
8:40 pm - 12:15 am
ORD
-
POS
26h 35m
1 stop
$319Air Canada
Fri, May 22 - Fri, Jun 19
Air Canada Logo
1:25 am - 6:47 pm
POS
-
ORD
18h 22m
2 stops
Air Canada Logo
8:45 am - 12:15 am
ORD
-
POS
14h 30m
2 stops
$322Air Canada
Sun, Jul 19 - Fri, Aug 14
Air Canada Logo
1:25 am - 6:47 pm
POS
-
ORD
18h 22m
2 stops
Air Canada Logo
2:19 pm - 12:15 am
ORD
-
POS
56h 56m
2 stops
$333Air Canada
Wed, May 27 - Wed, Jun 24
Air Canada Logo
1:25 am - 6:47 pm
POS
-
ORD
18h 22m
2 stops
Air Canada Logo
8:45 am - 12:15 am
ORD
-
POS
14h 30m
2 stops
$372Air Canada
Wed, May 27 - Thu, Jun 18
Air Canada Logo
1:25 am - 6:47 pm
POS
-
ORD
18h 22m
2 stops
Air Canada Logo
6:22 pm - 12:15 am
ORD
-
POS
28h 53m
2 stops
$386Air Canada
Wed, May 27 - Wed, Jun 24
Air Canada Logo
1:25 am - 7:50 am
POS
-
ORD
31h 25m
2 stops
Air Canada Logo
2:15 pm - 12:15 am
ORD
-
POS
9h 00m
1 stop
$389Air Canada
Sun, Apr 5 - Fri, Apr 10
Air Canada Logo
1:20 am - 10:53 am
POS
-
ORD
34h 33m
2 stops
Air Canada Logo
2:00 pm - 12:20 am
ORD
-
POS
9h 20m
1 stop
$405Air Canada
Sun, Jul 19 - Fri, Aug 14
Air Canada Logo
1:25 am - 8:16 pm
POS
-
ORD
19h 51m
1 stop
Air Canada Logo
7:25 am - 12:15 am
ORD
-
POS
15h 50m
1 stop
$426Air Canada
Wed, May 27 - Wed, Jun 17
Air Canada Logo
1:25 am - 6:47 pm
POS
-
ORD
18h 22m
2 stops
Air Canada Logo
8:45 am - 12:15 am
ORD
-
POS
14h 30m
2 stops
$442Air Canada
Booking Insights

KAYAK's insights & trends for flights to Chicago

Get data-powered insights and trends for flights to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly to Chicago O'Hare Intl Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights to Chicago O'Hare Intl Airport, 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 to Chicago O'Hare Intl Airport is March, where tickets cost $322 on average for one-way flights. On the other hand, the most expensive months are April and August, where the average cost of tickets from Trinidad and Tobago is $1,481 and $829 respectively. For return trips, the best month to travel is March with an average price of $322.

Good to know

Low seasonMarch
Cheapest flight$183
Best time to beat the crowds with an average 50% drop in price.
Most popular time to fly and prices are also 8% lower on average.
Flight from Port of Spain to Chicago

FAQs - booking Chicago flights

  • How far is Chicago O'Hare Intl Airport from central Chicago?

    The distance between Chicago O'Hare Intl Airport and downtown Chicago is 16 miles.

  • How does KAYAK find such low prices on flights 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 to Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights 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 with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight 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 up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • How many direct flights to Chicago O'Hare Intl Airport are there each week?

    Each week there are around 9,854 direct flights from within Trinidad and Tobago to Chicago O'Hare Intl Airport. The most common day for departures is Sunday, with 16% of flights taking off on this day.

Top tips for finding cheap flights to Chicago

  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.

Reviews of the top 3 airlines serving from Trinidad and Tobago to Chicago

 
See real verified KAYAK customer reviews for airlines flying to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from Trinidad and Tobago to Chicago. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with 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.
7.5
Copa AirlinesOverall score based on 1559 reviews
7.4Comfort
6.8Food
8.1Crew
7.8Boarding
6.8Entertainment
Airline reviews

Flight got delayed; had to go through security three times.

2.0 MediocreAnonymous, Feb 2026
PTY - JFK
Read more Copa Airlines reviews

Flight got delayed; had to go through security three times.

A lot things happened in this trip.The fly should be less stress.

There should be a warning regarding the quality of the aircraft on the website as we reserve the tickets. There was no TV or any type of screen onboard. The wifi they offer is good for nothing. Traveling 9 hours straight with kids and no type of entetainment was horrible. I wish I had been informed prior so I could buy a ticket with another airline. The food was a joke too. A very tiny portion per passenger. They also charged $100 per checked bag. With United I used to pay $60. So, fair to say that I wont be flying Copa anymore. Their aircraft was super old, outdated, no entertainment, with nearly no onboard food.

The flight was good overall. Everything went smoothly, although the landing was a bit rough. Still, it was a pleasant experience

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

They never clean the toilet, and the food is worse

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Chargers didn’t work, no entertainment and we had to wait for taxiing for easily 40 minutes after arriving early. Bags were late too!

No real complaints. The in flight food was much better than I expected. The in flight entertainment was excellent.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

Horrible Flight significantly delayed. Not due to united issue. But trying to rebook connection flight and get information about overnight accommodation was difficult. Agent did not seem to care or have any interest to help.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

This Japanese airline provides great service and very helpful in assisting their passengers.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

It was good experience this time. The flight was on time.

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

Overall, my last three trips on American Airlines have all been either delayed or "rescheduled" due to mechanical issues. At least on delay caused me to miss two possible connecting flights each later than the first. My last option for my last connection required the assistance of the onsite service desk (O'Hare Airport). The wait time for the service desk was such that it jeopardized getting booked on the last connecting flight available for the night. Suffice it to say, my latest experiences with American Airlines have caused me extensive loss of productive business and personal time and can therefore be classified as significantly less than satisfactory.

Waiting for gate in RDU for more than 20mins is crazy.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

Waited for oxygen tanks for 30 minutes after boarding was complete.

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

Flight from CHI to PVD was delayed by over 20 hours.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Gurnee
South Haven
Merrillville
Oak Brook
Saint Joseph
Tinley Park
Elk Grove Village
Des Plaines
Hammond
Hoffman Estates
Willowbrook
Portage
South Holland
Delavan
Northbrook
Lansing
Pleasant Prairie
Lisle
Elmhurst
Valparaiso

Everything you need to know for your flight to Chicago

Information on the airport you'll fly into in Chicago