$465 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 5/12. 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
$465
Overall average: $570
Multiple Airlines
mar. 5/12mar. 5/19
POS - ORD • 2 stops
Cheapest one-way
Multiple Airlines
dom. 1/18
POS - ORD • multi-stop
When to travel
December
Cheapest • 42% price drop
July
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

mar., may. 12 - mar., may. 19
Multiple Airlines Logo
2:45 pm - 8:51 am
POS
-
ORD
19h 06m
2 stops
Multiple Airlines Logo
8:20 pm - 12:15 am
ORD
-
POS
26h 55m
1 stop
$465Multiple Airlines
jue., mar. 5 - lun., mar. 9
JetBlue Logo
9:05 am - 10:59 pm
POS
-
ORD
15h 54m
1 stop
JetBlue Logo
12:41 pm - 6:17 am
ORD
-
POS
16h 36m
1 stop
$477JetBlue
dom., mar. 1 - lun., mar. 9
Air Canada Logo
2:20 am - 7:45 pm
POS
-
ORD
19h 25m
1 stop
Air Canada Logo
8:40 pm - 12:20 am
ORD
-
POS
26h 40m
1 stop
$478Air Canada
dom., mar. 1 - lun., mar. 9
Air Canada Logo
2:20 am - 11:18 am
POS
-
ORD
34h 58m
2 stops
Air Canada Logo
8:40 pm - 12:20 am
ORD
-
POS
26h 40m
1 stop
$481Air Canada
lun., mar. 9 - mié., mar. 18
Multiple Airlines Logo
9:10 am - 9:39 am
POS
-
ORD
25h 29m
1 stop
Multiple Airlines Logo
4:51 pm - 6:55 pm
ORD
-
POS
25h 04m
1 stop
$489Multiple Airlines
lun., mar. 9 - mié., mar. 18
Multiple Airlines Logo
9:10 am - 9:39 am
POS
-
ORD
25h 29m
1 stop
Multiple Airlines Logo
12:05 pm - 12:55 pm
ORD
-
POS
23h 50m
2 stops
$495Multiple Airlines
mar., may. 12 - mar., may. 19
JetBlue Logo
2:45 pm - 8:51 am
POS
-
ORD
19h 06m
2 stops
JetBlue Logo
6:00 am - 1:35 pm
ORD
-
POS
30h 35m
2 stops
$500JetBlue
dom., mar. 1 - lun., mar. 9
Air Canada Logo
2:20 am - 11:18 am
POS
-
ORD
34h 58m
2 stops
Air Canada Logo
6:04 pm - 12:20 am
ORD
-
POS
29h 16m
2 stops
$501Air Canada
jue., mar. 5 - lun., mar. 9
Multiple Airlines Logo
10:10 am - 12:40 am
POS
-
ORD
16h 30m
2 stops
Multiple Airlines Logo
8:40 pm - 12:20 am
ORD
-
POS
26h 40m
1 stop
$545Multiple Airlines
mié., may. 6 - dom., may. 10
Copa Airlines Logo
2:22 pm - 1:15 am
POS
-
ORD
11h 53m
1 stop
Copa Airlines Logo
8:02 am - 1:46 am
ORD
-
POS
16h 44m
1 stop
$574Copa Airlines
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 December, where tickets cost $375 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 December with an average price of $375.

Good to know

Low seasonMay
Cheapest flight$465
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly and prices are also 10% 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 11,014 direct flights from within Trinidad and Tobago to Chicago O'Hare Intl Airport. The most common day for departures is Thursday, 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 1559 reviews
6.8Entertainment
8.1Crew
7.4Comfort
7.8Boarding
6.8Food
Airline reviews

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

6.0 GoodIrma, Jan 2026
PTY - MIA
Read more Copa Airlines reviews

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

Horrible. No TV or any type of entertainment on board. Passwnger listening to/watching stuff on their own phone with no headphones making it noise and uncomfortable for everyone else, little/tiny food portions, old seats, useless wifi (cant access anything). Horrible exlerience especially it was a lomg distance flight with kids.

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.

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

They were super friendly bumped me up to exit row free of charge, All flight legs were on time

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

The flighr attandants were very rude they ignored me didnt offer me anything to drink throughoit the 4 hour flight i feel i was targeted and ignored because i was a darkskin latino man.

Perfect flight. Smooth flight. Arrived 20 minutes early at destination. Excellent service.

The flights were on time which was great give. It was holiday travel season and there’d been some weather issues. The only complaint and this is every time with United is the terrible seat design. The head rest is not built for comfort and having my neck bent forward for a cross country trip reminded me while I try not to take United flights as a rule.

Everything was absolutely wonderful from check in to baggage claim. Staff was very professional and sweet. Will definitely recommend United to family and friends.

The staff was nice, however boarding taking 2 hours. That’s insane. Overall very bad experience, a lot of turbulence and when landed in Chicago was horrible. I don’t think I’ll flight with UA again.

An international flight on an apron is pretty unusual in my 40 years of traveling. Departure delay. Luggage despite over an hour connection did not make it to the flight. Actually still in Germany. My luggage was not moved until I reached my final destination despite knowing it to be left in Germany upon my arrival in Chicago. The service left me a little off, both going and returning from Europe. Light on in the cabin even during a night flight and lots of traffic no matter what. Maybe passengers want more service? As a frequent traveler i just want to be able to sleep, the food will be better at the destination anyway. So since the cabin crew woke me up I asked for a cocktail, I did not get the best response although sitting in row 20 premium economy. I usually fly premium economy or business and my 2 flight to Europe in 2025 with United both had luggage delays and other minor issues. American flights to Australia, Canada and Europe went smoothly and Premium plus feels very much like business light. Is United Club becoming a waste and Silver/Gold levels another waste??

They did the one thing that really matters - got to Chicago early.

The flight was on time. I generally don’t drink or eat on short flights and the seats were good and the flight attendants were friendly. That’s all I expect

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Very bad! They kept delaying my flight and wouldn’t do anything about it

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.

Little warm on the plane and delayed for an hour

So excited very proud first of all I wanna thank kayak all updates very professional and fast alart And amazing cabin crew so nice to me they deserve big salute

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

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.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Gurnee
South Haven
Merrillville
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Saint Joseph
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Des Plaines
Hoffman Estates
Hammond
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Delavan
Northbrook
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Everything you need to know for your flight to Chicago

Information on the airport you'll fly into in Chicago