YTO - CHI

$97 Find Cheap Flights from Toronto 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 from Toronto to Chicago departing on 9/5. 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

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Toronto to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Toronto to Chicago, as well as popular online travel agencies
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Flights Deals

Cheap Flights from Toronto to Chicago (YTO-CHI)

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

Fri, Nov 7 - Sun, Nov 9
Air Canada Logo
12:05 pm - 1:01 pmYYZ-ORD
1h 56mnonstop
Air Canada Logo
3:55 pm - 6:34 pmORD-YYZ
1h 39mnonstop
$147Air Canada
Find Deal
Tue, Sep 16 - Mon, Sep 22
Porter Airlines Logo
3:35 pm - 4:24 pmYTZ-MDW
1h 49mnonstop
Porter Airlines Logo
5:20 pm - 8:02 pmMDW-YTZ
1h 42mnonstop
$149Porter Airlines
Find Deal
Thu, Sep 4 - Sun, Sep 7
Porter Airlines Logo
7:50 am - 8:39 amYTZ-MDW
1h 49mnonstop
Porter Airlines Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
$150Porter Airlines
Find Deal
Sat, Sep 13 - Sat, Sep 20
Air Canada Logo
3:25 pm - 8:11 pmYTZ-ORD
5h 46m1 stop
Air Canada Logo
3:35 pm - 9:34 pmORD-YTZ
4h 59m1 stop
$155Air Canada
Find Deal
Mon, Sep 1 - Wed, Sep 3
Air Transat Logo
9:00 am - 9:50 amYTZ-MDW
1h 50mnonstop
Air Transat Logo
9:35 am - 12:17 pmMDW-YTZ
1h 42mnonstop
$166Air Transat
Find Deal
Tue, Oct 7 - Wed, Oct 22
Air Transat Logo
3:35 pm - 4:24 pmYTZ-MDW
1h 49mnonstop
Air Transat Logo
5:20 pm - 8:02 pmMDW-YTZ
1h 42mnonstop
$187Air Transat
Find Deal
Wed, Aug 20 - Tue, Sep 2
United Airlines Logo
9:00 pm - 10:07 pmYYZ-ORD
2h 07mnonstop
United Airlines Logo
9:12 pm - 11:58 pmORD-YYZ
1h 46mnonstop
$189United Airlines
Find Deal
Thu, Oct 30 - Sun, Nov 2
United Airlines Logo
2:45 pm - 11:43 pmYYZ-ORD
9h 58m1 stop
United Airlines Logo
8:50 am - 2:14 pmORD-YYZ
4h 24m1 stop
$195United Airlines
Find Deal
Tue, Oct 7 - Sun, Oct 12
American Airlines Logo
6:00 am - 7:10 pmYYZ-ORD
14h 10m1 stop
American Airlines Logo
11:49 am - 2:30 pmORD-YYZ
1h 41mnonstop
$196American Airlines
Find Deal
Thu, Sep 4 - Mon, Sep 8
American Airlines Logo
7:35 am - 12:20 pmYYZ-ORD
5h 45m1 stop
American Airlines Logo
9:48 am - 5:15 pmORD-YYZ
6h 27m1 stop
$197American Airlines
Find Deal
Expert advice

Expert advice for your flight from Toronto to Chicago

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
Qatar Airways

Qatar Airways offers free checked bags in Economy, enhancing value for short-haul travelers.


Economy seats have 31 to 33 inches of pitch, providing decent comfort for short flights.

Porter Airlines

Porter Airlines' no middle seats policy ensures either window or aisle seating.


Porter offers free drinks including Canadian wines and craft beers, enhancing the travel experience.

Air Canada

Air Canada offers Preferred Economy seats with up to 4 extra inches of legroom.


Check-in online 24 hours before for priority boarding benefits with higher fare classes.

Read more about Air Canadaby Stefanie Waldek
American Airlines

American Airlines' Main Cabin Extra offers early boarding and complimentary drinks.


AA's Basic Economy has restrictions like late boarding and no free checked bags.

United Airlines

United offers Economy Plus seats with up to 6 extra inches of legroom.


United's Premier Access offers priority check-in and boarding for eligible passengers.

Airports
YYZ

For a smooth departure from YYZ, use the UP Express train. It runs every 15 minutes and takes 25 minutes to downtown Toronto.

Read more about YYZby Stefanie Waldek
ORD

Upon arrival at ORD, take the CTA Blue Line train to downtown Chicago. It runs 24/7 and takes about 45 minutes.

Read more about ORDby Stefanie Waldek
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on Qatar Airways, Air Canada, United Airlines, ORD and YYZ

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
John Walton

John Walton

Expert on Porter Airlines

John Walton

John Walton

Independent aviation journalist John Walton took his first flight at eight weeks old and hasn’t stopped travelling since. A world-renowned expert in airlines and the passenger experience, he writes in depth on aviation, is a resident expert on travel in Japan and France, and offers a uniquely queer perspective on travelling the world.

Read more
Harriet Baskas

Harriet Baskas

Expert on American Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Booking Insights

KAYAK's insights & trends for Toronto to Chicago flights

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

Find cheap flights to Chicago
Find cheap flights to Chicago

Planning a trip from Toronto to Chicago? KAYAK’s data-powered insights will help you find cheap flights. Learn the best time to fly, how early to book your ticket, and other tips to secure great prices.

What is the cheapest Toronto to Chicago flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Toronto to Chicago.

Our data shows that the cheapest route for a return flight from Toronto to Chicago cost $132 and was between Toronto Island Airport (YTZ) and Chicago Midway Airport (MDW). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $132.

What’s the cheapest day of the week to fly from Toronto to Chicago?

The average price of all round-trip flights from Toronto to Chicago clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Chicago on a Friday, as we generally find the cheapest rates on that day for this route. On the other hand, Monday is the most expensive day to fly from Toronto to Chicago. For your return ticket, we recommend flying on a Friday and avoiding Sundays for the best deals.

What is the cheapest month to fly from Toronto to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Toronto to Chicago, 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 from Toronto to Chicago is June, where tickets cost $224 (return) on average. On the other hand, the most expensive months are December and February, where the average cost of round-trip tickets is $300 and $289 respectively.

Can I save money by flying with a layover from Toronto to Chicago?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 1 stop layover the cheapest option at $323 on average.

How far in advance should I book a flight from Toronto to Chicago?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Toronto to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Toronto to Chicago, you should book around 3 weeks before departure, which saves you about 41% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 12 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$97
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly and prices are also 5% lower on average.
Flight from Toronto Island to Chicago Midway Airport

When to book flights from Toronto to Chicago

Are your dates flexible? Find out the best times to travel from Toronto to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

Flights from Toronto to Chicago: the best tips from KAYAK users' own experiences

Insights shared by verified travelers who flew the route from Toronto to Chicago 
BrianFlew with Air CanadaYYZ-ORDOct 2024
Be prepared for a labyrinthine experience traversing the various levels and passages of the Toronto airport. Bring quality walking shoes, as it is likely well over a km in total walking time.
Verified travelerFlew with United AirlinesYYZ-ORDMar 2024
Carry-on baggage sizing for United US bound flights appears to be much smaller than for Canadian flights, which forced me to check my bag at the last minute. So check online ahead of time

FAQs for booking flights from Toronto to Chicago

  • Can I fly from Toronto to Chicago non-stop?

    Flights from Toronto to Chicago are quite short, usually lasting less than 2 hours, which means they occur regularly and are often non-stop. Direct flights are offered by numerous airlines including American Airlines, Porter Airlines and Air Canada.

  • How do I get from downtown Toronto to Billy Bishop Airport?

    Getting from downtown Toronto to Billy Bishop Airport is simple. Passengers can choose the free express shuttle that goes from Toronto’s city centre to the mainland ferry terminal every 15 minutes. There is then an 800-meter pedestrian tunnel or a 90-second ride on the ferry, both going directly to the airport.

  • Are there on-site hotels at Billy Bishop Airport?

    While there are no airports directly inside Billy Bishop Airport, there are a number of nearby hotels like the Fairmont Royal York or the Strathcona Hotel. Both are located just minutes from Billy Bishop Airport and offer comfortable rooms and a number of amenities.

  • What is there to do at Toronto Pearson International Airport?

    If your plane was delayed or Toronto is just one leg of your journey, Toronto Pearson International Airport offers many opportunities to pass the time. The airport is fully equipped so that you can enjoy a number of shops and kiosks, a workout at Goodlife Fitness or a treatment at the spa. More interested in art? Check out the displays throughout the airport, featuring works by local artists.

  • What is the cheapest flight from Toronto to Chicago?

    In the last 3 days, the lowest price for a flight from Toronto to Chicago was $97 for a one-way ticket and $147 for a round-trip.

  • Do I need a passport to fly between Toronto and Chicago?

    Yes

  • Which airports will I be using when flying from Toronto to Chicago?

    On your way to Chicago, you’ll fly out from one of these Toronto airports: Toronto Island or Toronto Pearson Intl. You’ll be landing in one of Chicago’s 2 airports: Chicago Midway or Chicago O'Hare Intl.

  • Which airlines offer Wi-Fi service onboard planes from Toronto to Chicago?

    Air Canada, United Airlines, and American Airlines offer inflight Wi-Fi service on the Toronto to Chicago flight route.

  • Which aircraft models fly most regularly from Toronto to Chicago?

    The De Havilland (Bombardier) DHC-8-400 Dash 8Q is the aircraft model that flies most regularly on the Toronto to Chicago flight route.

  • Which airline alliances offer flights from Toronto to Chicago?

    oneworld, and Star Alliance are the airline alliances operating flights between Toronto and Chicago, with oneworld being the most commonly used for this route.

  • On which days can I fly direct from Toronto to Chicago?

    There are nonstop flights from Toronto to Chicago on a daily basis.

  • Which is the best airline for flights from Toronto to Chicago, Porter Airlines or Air Transat?

    The two airlines most popular with KAYAK users for flights from Toronto to Chicago are Porter Airlines and Air Transat. With an average price for the route of $257 and an overall rating of 8.0, Porter Airlines is the most popular choice. Air Transat is also a great choice for the route, with an average price of $288 and an overall rating of 7.7.

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

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

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

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

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

KAYAK’s top tips for finding a cheap flight from Toronto to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $156 or less one-way and $248 or less round-trip.
  • Flights from Toronto to Chicago usually depart from Lester B. Pearson International Airport, located 22.5 km northwest of Toronto’s city centre, and land at O’Hare International Airport, located 23 km northwest of downtown Chicago. Flights might also depart from the smaller Billy Bishop Toronto City Airport, located on the Toronto Island, and could land at Chicago Midway International Airport, 13 km from the Loop business district in Chicago.
  • Travelling with kids and worried about entertaining them before your flight? Don’t be, Toronto Pearson International Airport offers two child play areas located in both Terminal 1 and Terminal 3. These areas are fully equipped to keep your children occupied with toys, games and books.
  • As Chicago O’Hare is one of the largest airports in the area, it is no surprise that it features a plethora of things to do, should you have some time to spare. To take care of your mind and body, head to the Health Club for a run or to the Yoga Room to relax and stretch. The airport is also home to dozens of shops that offer many options for gifts and souvenirs. If you like art, enjoy the sculptures, paintings and murals scattered throughout the airport. Passengers can also take a walk in the Urban Garden to admire the different plant species present there.
  • If your flight has arrived late and you don’t want to travel into Chicago late at night, book a room at the Hilton Chicago O’Hare Airport Hotel, located across from Terminal 2. Alternatively, you can also stay in one of the hotels located just minutes from the airport such as the Sheraton Chicago O’Hare, the Aloft Chicago O’Hare or the Embassy Suites Chicago O’Hare Rosemont.
  • Getting from Chicago O’Hare to downtown Chicago is quite easy. The Amtrak train connects the airport and the city center in about 40 minutes, and there are also numerous CTA bus lines connecting the airport to various destinations in the city. The L train line also offers a 24-hour service to reach the city centre.

Prefer to fly direct from Toronto to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Toronto to Chicago.
Find which airlines fly direct from Toronto to Chicago, which days they fly and book direct flights.

Direct departures

Toronto to Chicago

Monday

Air Canada, American Airlines, Porter Airlines, +1 more

Air Canada, American Airlines, +2 more

Tuesday

Air Canada, American Airlines, Porter Airlines, +1 more

Air Canada, American Airlines, +2 more

Wednesday

Air Canada, American Airlines, Porter Airlines, +1 more

Air Canada, American Airlines, +2 more

Thursday

Air Canada, American Airlines, Porter Airlines, +1 more

Air Canada, American Airlines, +2 more

Friday

Air Canada, American Airlines, Porter Airlines, +1 more

Air Canada, American Airlines, +2 more

Saturday

Air Canada, American Airlines, Porter Airlines, +1 more

Air Canada, American Airlines, +2 more

Sunday

Air Canada, American Airlines, Porter Airlines, +1 more

Air Canada, American Airlines, +2 more

See more direct flights

Direct returns

Chicago to Toronto

Monday

Air Canada, American Airlines, Porter Airlines, +1 more

Air Canada, American Airlines, +2 more

Tuesday

Air Canada, American Airlines, Porter Airlines, +1 more

Air Canada, American Airlines, +2 more

Wednesday

Air Canada, American Airlines, Porter Airlines, +1 more

Air Canada, American Airlines, +2 more

Thursday

Air Canada, American Airlines, Porter Airlines, +1 more

Air Canada, American Airlines, +2 more

Friday

Air Canada, American Airlines, Porter Airlines, +1 more

Air Canada, American Airlines, +2 more

Saturday

Air Canada, American Airlines, Porter Airlines, +1 more

Air Canada, American Airlines, +2 more

Sunday

Air Canada, American Airlines, Porter Airlines, +1 more

Air Canada, American Airlines, +2 more

See more direct flights

Reviews of the top 5 airlines serving from Toronto to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Toronto to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Toronto 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.
8.0
Porter AirlinesOverall score based on 318 reviews
7.0Entertainment
8.2Boarding
7.6Food
8.7Crew
8.0Comfort
Airline reviews

All good the seats a little tight and no I pad screen

10.0 ExcellentAnonymous, Jul 2025YYZ - RSW
Read more Porter Airlines reviews

All good the seats a little tight and no I pad screen

Everything was good except the fact you charge more for a carry on bag vs a check in bag and to top it off in US$ that was not impressive

Our flight was cancelled at the last minute for maintenance reasons and we were rebooked on a late flight when we purposefully booked our flight to be home early due to work.

Seemed like an old plane. Very noisy. The seat cushions were so old that the metal bracing of the seats were poking through. There was plenty of leg room though.

Flight was delayed over 2 hours, then landed at a different airport!

The whole experience from check in to deboarding was fantastic.

Just an evening before they canceled my ticket and offered me ticket costing 3 x times more than. I will not fall prey to these scams,Will never book through kayak now. Such a bad experience.

was okay except.. 1)the porter check in webpage doesn't let you print your boarding pass from home 2)that there was a 90 min cut off for checking in on the kiosk in general, and to print a boarding pass, even tho i checked in online already....

Great! Personable crew. I love that they pour complimentary beer and wine.

I love the 2 seats per row. More room. The crew were excellent.

Check in slow even though completed online check in, there was no bag drop available so had to query for 90mins as only 2 staff on desks.

Flying to a far away destination is a miracle in itself, so please take these with a grain of salt. The seats are a bit tired, and need a freshen up. The entertainment could be a bit newer, especially with all services available now. The food really is where we need help. But again, flying is a privilege, so all is good.

Not so much porter it's your site! Not good

They are a sister company with Air Transat and the two companies do not work well together. If you have any issues the two companies will blame each other and you will miss your flights. The help line does not help

Never book through a third party. Book through Air transats website. Terrible process to get help and many issues happen with them and sister companies because half the flights you book with them aren’t even through air transat.

The plane was pretty full, and we dis not have any includes meal for our 4h30 flight? And on-board entertainment wasn't available, there was no TV or plugging to charger your device on the plane. They told us to download an app if we wanted to watch movies but it never connected, that was a disappointment, the r we st was very good though and the crew were really nice!

Seats were very tight especially for first leg of trip.

Not necessarily a Transat issue but it took 2 hours to go through immigration. Tried to reach out to Transat for resolution but was unable to reach an agent.

The flight was excellent, once it started, however we were delayed two hours when the first plane’s engines wouldn’t start. They found another identical plane and transferred us and our luggage in under two hours and made up almost an hour in the air.

Really low cost trip for the huge amount I paid…o paid 550 dollars just for the trip, one way trip, plus 95 for 1 luggage’s and the second 135 dollars…no blanket, not headphones for entertainment, food was served after 3 hours and 2 hours after, breakfast was served Bad, low cost company for high prices

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.

Overall a very poor experience - booked premium economy tickets but due to last minute flight delays , all my itinery went for a toss and had to fly economy class with no access to lounge or any compensation by united airlines to make up for the flight delays . i had expected better experience than that from united.

It was fine, definitely older planes with no charging or anything. There’s no entertainment set up on board, but it is nice that they allow you to access the in flight entertainment from your phone without having to pay for the Wi-Fi and they do offer free texting.

I liked that the flight was nonstop from ORD to CIU for $200 round trip.

All flight attendants could benefit by taking an international flight on Qantas Airline. Qantas attendants are much more hospitable in every way. Much superior than and attendants on any US airline.

While the staff was pleasant and helpful, the following observations are for your awareness. There was some delay on the tarmac on take off and landing. The paid lunch/food offerings were limited. Entertainment was only available on WiFi at a cost.

The first flight was better in terms of the aircraft.

So far so good but food and entertainment are not available for this flight

Smooth flight. Boarding was chaotic. Could not hear the gate agent over the intercom. People were lined up in the wrong lines. Groups one and two were told to board through line one and group 3 through line 2. All very confusing. Once in the air, the flight was smooth. There was no entertainment option on this aircraft, even though it was a larger aircraft.

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

Very clean and comfortable cabin. Amazing Mediterranean salad for lunch before landing. Great range of films to watch. Really quiet and easy to sleep on the flight also. The initial food was a bit weird: odd fried chicken pieces in some weird white gloop, but that would be my lack of cultural knowledge on the grub. Salad more than made up for it at the other end. Staff were super attentive and helpful. Great and easy flight

The flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

The flight was fine but the 8 hour delay in Chicago was awful - 5 gate changes and repeated delays without an explanation. No vouchers. Nothing.

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

The flight was 2 hour delayed, otherwise everything was excellent. The delay was due to the hourly limit requirement so given that as a reason, I'm happy with the flight!

Not sure the logic of the boarding in Groups. I was loaded first on the aisle. Then the guy in the middle. Then the guy by the window. Constantly holding up the other people boarding behind them with us blocking the aisle and this happened in most of the other rows

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Crew professional. Easy bag drop off. On time. Good entertainment.

Flight got delayed for no reason. And Air Canada was doing 3 boardings via the same gate. It was chaotic!

Wonderful airline. All staff were pleasant and helpful. What is sad is that it wasn’t grand gestures just everyday pleasantness and friendliness that are missing from the other airlines I have flown recently.

Friendly efficient crew, but plane had no way to charge phone. That is a near necessity with today’s travel where we carry out travel documents on our phones.

Bad service as well. Another 3hr delayed flight from chicago to Charlotte.

Orlando to Canada, despite being close and an international flight, the plane was not at all comfortable. It felt like the chair was being pushed forward, in addition to not having a TV and having to choose from a tiny glass of drink, for example, water or soda. I couldn't have both. When I asked the flight attendant for an extra glass of water, she looked at me with an ugly face. This is ridiculous. They don't want to give water to passengers. I will never fly with this airline again in my life.

Very bad service the way back we was on the way for r two days very bad condition and waiting for luggage till now

United had no (zero) record of our flight. It took over an hour of us standing in line with surly employee while others waited to get resolved. I have never experienced such poor service and poor empathy.

In a nutshell, my bag, the one I have to pay for, because now you can’t even bring a carry on, did not make it. I am still waiting for an update. The fact that not only were have to pay for it, but on top of that we are stuck without getting it, it’s ridiculous..

This was an excellent experience for a very short flight.

No space in overhead bin, one cookie, 2 oz of juice - is not customer service.

Everything you need to know for your flight from Toronto to Chicago

Cabin class types available on flights from Toronto to Chicago

Cabin classes available on flights from Toronto to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

Compare transportation modes for Toronto to Chicago

Transportation modeAverage priceAverage duration
Flights$1,5981h 49m
Buses$12615h 14m

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