$414 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 1/23. 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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Everything you should know

Cheapest round-trip
$414
Typical prices: $579-$618
JetBlue
Fri 1/23Mon 1/26
POS - ORD • 2 stops
Cheapest one-way
$580
Multiple Airlines
Sun 1/4
POS - ORD • 3 stops
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
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!
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, Jan 23 - Mon, Jan 26
JetBlue Logo
8:20 am - 5:44 pmPOS-ORD
35h 24m2 stops
JetBlue Logo
7:45 am - 7:15 pmORD-POS
33h 30m2 stops
$414JetBlue
Find Deal
Fri, Jan 23 - Mon, Jan 26
Multiple Airlines Logo
9:10 am - 8:09 amPOS-ORD
24h 59m1 stop
Multiple Airlines Logo
6:57 pm - 6:55 pmORD-POS
21h 58m1 stop
$435Multiple Airlines
Find Deal
Thu, Jan 22 - Mon, Jan 26
Air Canada Logo
2:20 am - 3:10 pmPOS-ORD
14h 50m1 stop
Air Canada Logo
8:45 pm - 1:20 amORD-POS
26h 35m1 stop
$463Air Canada
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Fri, Jan 23 - Mon, Jan 26
Multiple Airlines Logo
10:10 am - 10:46 pmPOS-ORD
14h 36m2 stops
Multiple Airlines Logo
6:57 pm - 6:55 pmORD-POS
21h 58m1 stop
$466Multiple Airlines
Find Deal
Thu, Jan 15 - Mon, Jan 19
Air Canada Logo
2:20 am - 1:01 pmPOS-ORD
12h 41m1 stop
Air Canada Logo
6:00 pm - 1:20 amORD-POS
29h 20m2 stops
$483Air Canada
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Thu, Jan 8 - Thu, Jan 15
Multiple Airlines Logo
10:10 am - 8:30 pmPOS-ORD
12h 20m1 stop
Multiple Airlines Logo
6:57 pm - 6:55 pmORD-POS
21h 58m1 stop
$511Multiple Airlines
Find Deal
Fri, Jan 23 - Mon, Jan 26
Multiple Airlines Logo
9:10 am - 2:19 pmPOS-ORD
31h 09m2 stops
Multiple Airlines Logo
4:38 pm - 1:20 amORD-POS
30h 42m3 stops
$534Multiple Airlines
Find Deal
Thu, Jan 22 - Mon, Jan 26
Multiple Airlines Logo
2:20 am - 2:55 pmPOS-ORD
14h 35m2 stops
Multiple Airlines Logo
4:38 pm - 1:20 amORD-POS
30h 42m3 stops
$538Multiple Airlines
Find Deal
Wed, Jan 7 - Wed, Jan 14
Multiple Airlines Logo
9:10 am - 5:00 pmPOS-ORD
9h 50m1 stop
Multiple Airlines Logo
9:14 am - 6:55 pmORD-POS
31h 41m1 stop
$555Multiple Airlines
Find Deal
Thu, Jan 8 - Thu, Jan 15
Multiple Airlines Logo
10:10 am - 7:17 pmPOS-ORD
11h 07m1 stop
Multiple Airlines Logo
9:00 pm - 8:00 pmORD-POS
21h 00m2 stops
$563Multiple Airlines
Find Deal
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$414
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 - 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 12,888 direct flights from within Trinidad and Tobago to Chicago O'Hare Intl Airport. The most common day for departures is Monday, 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.
7.6
Copa AirlinesOverall score based on 1568 reviews
8.1Crew
6.8Entertainment
6.8Food
7.4Comfort
7.8Boarding
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?

Book flights to Chicago if you plan to visit one of these locations
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South Haven
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Oak Brook
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Elk Grove Village
Hoffman Estates
Des Plaines
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Everything you need to know for your flight to Chicago

Information on the airport you'll fly into in Chicago