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$358 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 8/2. 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
0 bags
土 6/8
土 6/15

Search hundreds of travel sites at once for deals on flights to Chicago

 
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
In the last 7 days travelers have searched 43,895,468 times on KAYAK, and here is why:

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Flights to Chicago - Travel Insights & Trends

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 day to fly to Chicago?

The average price of all flights to Chicago O'Hare Intl Airport clicked on KAYAK for each day over the last 12 months.
Based on KAYAK data, the cheapest day to fly to Chicago is Wednesday where tickets can be as cheap as $568. On the other hand, the most expensive day to fly is Monday, where prices are $733 on average.

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 April, where tickets cost $525 on average for one-way flights. On the other hand, the most expensive months are June and January, where the average cost of tickets from Trinidad and Tobago is $819 and $810 respectively. For return trips, the best month to travel is April with an average price of $525.

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

The average price for all flights to Chicago O'Hare Intl Airport depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.
The cheapest time of day to fly to Chicago O'Hare Intl Airport is generally in the morning, when flights cost $613 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 $678.

How long is the flight to Chicago O'Hare Intl Airport?

The duration of your flight to Chicago depends on your departure and arrival airports. Obviously any flights that include a layover will also be longer. The most popular route to Chicago on KAYAK is from Port of Spain, which takes 10h 51m.

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

There are around 1,542 direct flights from within Trinidad and Tobago to Chicago O'Hare Intl Airport every day. Most flights depart in the morning, with 6:00 am the most common departure time and 52% of flights departing in the morning.

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

Each week there are around 10,788 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.

Good to know

Low season

November

High season

December

Cheapest flight

$358
Best time to beat the crowds but there is an average 12% increase in price.
Most popular time to fly and prices are also 2% lower on average.
Flight from Port of Spain to Chicago

FAQs - booking Chicago flights

  • How far is Chicago from central Chicago?

    The distance between Chicago 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.

  • Which airline offers the most flights to Chicago O'Hare Intl Airport?

    Of the 12 airlines that fly to Chicago O'Hare Intl Airport, United Airlines offers the most flights, with around 5,208 per week, followed by American Airlines with 4,263 flights per week.

See more FAQs

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.

Prefer to fly non-stop to Chicago O'Hare Intl?

Find which airlines fly direct to O'Hare Intl, which days they fly and book direct flights.

Nonstop departures

Trinidad and Tobago to Chicago O'Hare Intl

Monday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +77 more

ANA, Aer Lingus, +78 more

Wednesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Thursday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

Saturday

ANA, Aer Lingus, Aerolineas Argentinas, +77 more

ANA, Aer Lingus, +78 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +77 more

ANA, Aer Lingus, +78 more

See more direct flights

Nonstop returns

Chicago O'Hare Intl to Trinidad and Tobago

Monday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +77 more

ANA, Aer Lingus, +78 more

Wednesday

ANA, Aer Lingus, Aeromexico, +77 more

ANA, Aer Lingus, +78 more

Thursday

ANA, Aer Lingus, Aeromexico, +76 more

ANA, Aer Lingus, +77 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

Saturday

ANA, Aer Lingus, Aerolineas Argentinas, +77 more

ANA, Aer Lingus, +78 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +77 more

ANA, Aer Lingus, +78 more

See more direct flights
See more direct flights

Top airlines flying 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.
7.4
United AirlinesOverall score based on 11027 reviews
8.1Crew
7.1Entertainment
7.2Comfort
6.7Food
7.7Boarding
Airline reviews

It was good! Appreciated that it was very on schedule so it made the connecting flight less stressful

8.0 ExcellentAnonymous, Apr 2024YUL - ORD
Read more about United Airlines reviews

It was good! Appreciated that it was very on schedule so it made the connecting flight less stressful

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

We were delayed an hour leaving Munich (No fault of the crew). They kept us posted on the status so we knew what was going on, but as a result we missed our connection in Chicago and the communication on connecting flights was pretty poor as we disembarked. It was already stressful and some of that could have been reduced by better communications about where to find transfers, etc.

One problem, but a serious one - the plane is built with electric windows that tint dark to reduce light. Sitting next to the window is VERY UNCOMFORTABLE as it emits so much HEAT in the face when tinted.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

Wifi wasn't working on one of the UA flights after boarding.

The flight was delayed instead of leaving at 11 it left at 12.20

United WiFi is consistently unusable (it can take 10 mins to load a single web page). If you need Wifi to do work, be prepared to lose half a day of productivity.

Crew was not very helpful. They forgot to serve me coffee and had to wait for a long time.It looked as if they were not very happy with what they were doing.

Good movies, iffy pay WiFi, food ok- on time though and that was great!

Left on time. Arrived early. Turbulence coming in and gate not open due to early arrival but expected.

The CX617 from HK to BKK was delayed more than 1.5 hours.

The plane was old and in new of a cleaning up and renovating on the interior. Seats and carpets were very worn and dirty looking. Cushioning on the seats was broken down and not as comfortable as newer jet seats. Food was a little below average but okay. Staff were friendly and hard working but did not pick up debris or food they spilled when collecting from the customers. But they were very helpful and professional.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight got canceled due to mechanical issues, and he to be rebooked and missed my appointments for that day

The flight was scheduled to depart DCA at 12:30 pm but was delayed twice on the ground so that we were finally scheduled to depart at around 4:00 pm. Once we boarded, it was announced that takeoff would be delayed again to fix a hydraulic problem which delayed our eventual takeoff until around 5:00 pm. Once we departed, it was a smooth flight back to ORD. We did not get any explanation about what caused the original significant delay. In my experience, this happens frequently with AA.

Book cheap flights from Trinidad and Tobago to Chicago

Recent round-trip flight deals

 
These are the cheapest round-trip flights to Chicago found on KAYAK in the last 72 hours.
8/2
2 stopsFrontier
10h 45mPOS-ORD
8/7
2 stopsFrontier
21h 16mORD-POS
$358
7/26
2 stopsFrontier
33h 51mPOS-ORD
8/10
2 stopsFrontier
22h 56mORD-POS
$408
9/5
1 stopAmerican Airlines
9h 16mPOS-ORD
9/18
1 stopAmerican Airlines
8h 29mORD-POS
$463
9/23
1 stopUnited Airlines
13h 22mPOS-ORD
9/29
1 stopUnited Airlines
14h 48mORD-POS
$464
9/24
2 stopsAmerican Airlines
14h 36mPOS-ORD
9/29
1 stopAmerican Airlines
16h 41mORD-POS
$467
9/24
2 stopsAmerican Airlines
14h 36mPOS-ORD
9/29
2 stopsAmerican Airlines
13h 25mORD-POS
$487
9/23
1 stopUnited Airlines
17h 37mPOS-ORD
9/28
1 stopUnited Airlines
11h 48mORD-POS
$516
6/24
2 stops
21h 50mPOS-ORD
7/1
1 stop
24h 21mORD-POS
$598
10/25
1 stopCopa Airlines
10h 11mPOS-ORD
10/29
1 stopCopa Airlines
16h 47mORD-POS
$636
6/24
1 stop
24h 51mPOS-ORD
7/1
1 stop
24h 21mORD-POS
$663

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Flights to Chicago

Destination:

Chicago (ORD)United States

Return flight deals:

Chicago - Trinidad and Tobago

Cabin classes: