$463 Find Cheap Flights from Trinidad and Tobago to Chicago

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 10/24. 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

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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
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

Fri, Oct 24 - Wed, Nov 19
Air Canada Logo
2:25 am - 3:04 pmPOS-ORD
13h 39m1 stop
Air Canada Logo
8:15 pm - 1:10 amORD-POS
26h 55m1 stop
$463Air Canada
Find Deal
Fri, Oct 24 - Mon, Nov 17
Multiple Airlines Logo
2:25 am - 7:24 pmPOS-ORD
17h 59m1 stop
Multiple Airlines Logo
5:10 am - 8:00 pmORD-POS
12h 50m1 stop
$469Multiple Airlines
Find Deal
Fri, Nov 14 - Wed, Nov 26
Multiple Airlines Logo
9:10 am - 9:47 amPOS-ORD
26h 37m1 stop
Multiple Airlines Logo
3:43 pm - 8:00 pmORD-POS
26h 17m1 stop
$477Multiple Airlines
Find Deal
Thu, Nov 13 - Wed, Nov 26
Air Canada Logo
2:15 am - 7:30 pmPOS-ORD
19h 15m1 stop
Air Canada Logo
8:15 pm - 1:10 amORD-POS
26h 55m1 stop
$482Air Canada
Find Deal
Sat, Oct 25 - Mon, Nov 17
Multiple Airlines Logo
9:10 am - 11:29 pmPOS-ORD
15h 19m2 stops
Multiple Airlines Logo
12:17 pm - 6:55 pmORD-POS
28h 38m1 stop
$486Multiple Airlines
Find Deal
Fri, Nov 14 - Wed, Nov 26
American Airlines Logo
4:30 pm - 8:55 amPOS-ORD
18h 25m1 stop
American Airlines Logo
5:00 am - 11:38 pmORD-POS
16h 38m1 stop
$574American Airlines
Find Deal
Fri, Nov 14 - Wed, Nov 26
American Airlines Logo
4:30 pm - 8:55 amPOS-ORD
18h 25m1 stop
American Airlines Logo
8:20 am - 11:38 pmORD-POS
13h 18m2 stops
$579American Airlines
Find Deal
Tue, Nov 11 - Fri, Dec 12
United Airlines Logo
1:30 am - 7:56 pmPOS-ORD
20h 26m1 stop
United Airlines Logo
9:08 pm - 12:23 amORD-POS
25h 15m1 stop
$593United Airlines
Find Deal
Fri, Feb 27 - Tue, Mar 3
Copa Airlines Logo
2:16 pm - 12:04 amPOS-ORD
11h 48m1 stop
Copa Airlines Logo
7:34 am - 1:15 pmORD-POS
27h 41m1 stop
$653Copa Airlines
Find Deal
Fri, Feb 27 - Tue, Mar 3
Copa Airlines Logo
2:16 pm - 12:31 pmPOS-ORD
24h 15m1 stop
Copa Airlines Logo
2:22 pm - 1:46 amORD-POS
9h 24m1 stop
$670Copa Airlines
Find Deal

Everything you should know

When to travel
June
Cheapest • 34% price drop
December
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Cheapest round-trip
$463
Overall average: $676
Air Canada
Fri 10/24Wed 11/19
POS - ORD • 1 stop
Cheapest one-way
Multiple Airlines
Tue 10/14
LAX - ORD • multi-stop
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
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 June, where tickets cost $453 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 $1,475 and $829 respectively. For return trips, the best month to travel is June with an average price of $453.

Good to know

Low seasonJune
Cheapest flight$463
Best time to beat the crowds with an average 34% drop in price.
Most popular time to fly with an average 2% increase in price.
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.

  • What is the cheapest day to fly to Chicago?

    Based on KAYAK data, the cheapest day to fly to Chicago is Thursday where tickets can be as cheap as $603. On the other hand, the most expensive day to fly is Wednesday, where prices are $717 on average.

  • 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.

  • What is the cheapest time of day to fly to Chicago O'Hare Intl Airport?

    The cheapest time of day to fly to Chicago O'Hare Intl Airport is generally in the morning, when flights cost $637 on average. The most expensive time of day to fly to Chicago O'Hare Intl Airport is generally in the evening, which is peak travel time and where the average cost of a ticket is $672.

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

    Each week there are around 12,653 direct flights from within Trinidad and Tobago to Chicago O'Hare Intl Airport. The most common day for departures is Friday, with 15% 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.
7.6
Copa AirlinesOverall score based on 1547 reviews
7.4Comfort
7.8Boarding
8.1Crew
6.8Entertainment
6.8Food
Airline reviews

I liked the meatloaf the chicken was awful but the plane was on time and got there and the staff was nice.

10.0 ExcellentSherry, Oct 2025ORD - PTY
Read more Copa Airlines reviews

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.

It was ok. However, the food was quite poor since I don't eat pasta.

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.

There was no individual at the front check in when I arrived. I waited for at least 15 minutes and walked around asking security/janitors if they could help and they did not have a solution. So I had to take my checked bag through security and they threw away some of my items. I ended up making it to the gate only a few minutes before it closed due to my waiting for an agent at check in.

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

Excellent experience. Starting with the agent at the Premier bag drop who noticed I was very early for my scheduled flight and offered to rebook me on an earlier flight with my seat preference. She would not let me leave the counter until she knew that all of the changes and new boarding pass showed up on my United app. At the gate, the flight boarded quickly such that we departed early and the flight was smooth. We arrived 20 minutes early at ORD and I was able to be home in time for dinner. One of the best flights I've had.

Salina to travers city was great! But the sept 24 Tranverse city was not! Traverse city to chichago was cancelled, i went to Denver & got to Salina 6 hours later!

See previous note about the passenger in Denver who threw my husband's bag out of the overhead bin in order to maker room for his own. And the flight attendant back up the new passenger.

Could have said yes to a glass of wine 🍷 instead of saying we'll come around in a couple of hours

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

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.

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

The flight was on time and crew were nice, seats were tight and there was entertainment available

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.

Traveling to a place near Chicago?

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

Everything you need to know for your flight to Chicago

Information on the airport you'll fly into in Chicago

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.