YTO - CHI

$123 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 6/10. 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

 
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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Everything you should know

Cheapest round-trip
$192
Typical prices: $176-$238
Porter Airlines
Thu 4/16Mon 4/20
YTZ - MDW • Non-stop
Cheapest one-way
$123
Typical prices: $156-$221
Porter Airlines
Wed 6/10
YTZ - MDW • Non-stop
Advice from real travelers
AI-powered summary based on content written by travel experts and KAYAK users. AI can make mistakes.
Porter Airlines' no middle seats policy ensures comfort.
United's carry-on size is smaller for US-bound flights.
Expert advice
Expert advice
+1
+1
Expert advice
Expert advice
+1
Top airlines
Cheapest • from $192 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
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Airline reviews
Airline reviews
+1
Nonstop flights
You can fly direct with Air Canada, American Airlines and others. Average duration is 2h 02m
Direct flights
Direct flights
+1
+1
Direct flights
Direct flights
+1
Top routes
Cheapest • 19% average savings
Most popular
Insights
Insights
Insights
Insights
Avoid delays
Most punctual • 92% on-time
Best time • Fewest delays
Insights
Insights
Insights
Insights
When to book
in advance
Our data shows that travelers who book at least 4 weeks in advance save around 54% compared to booking last minute.
Insights
Insights
Insights
Insights
When to travel
Cheapest • 14% price drop
Most popular
Good to know
Good to know
+1
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Good to know
Good to know
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Flight Deals
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Expert advice
Flight 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

Thu, Apr 16 - Mon, Apr 20
Porter Airlines Logo
9:25 am - 10:15 am
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
11:00 am - 1:42 pm
MDW
-
YTZ
1h 42mnonstop
$192Porter Airlines
Thu, Apr 16 - Mon, Apr 20
Porter Airlines Logo
9:25 am - 10:15 am
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
11:00 am - 1:42 pm
MDW
-
YTZ
1h 42mnonstop
$193Porter Airlines
Thu, Apr 16 - Mon, Apr 20
Porter Airlines Logo
9:25 am - 10:15 am
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
11:00 am - 1:42 pm
MDW
-
YTZ
1h 42mnonstop
$194Porter Airlines
Thu, Apr 16 - Mon, Apr 20
Air Canada Logo
8:15 am - 9:10 am
YYZ
-
ORD
1h 55mnonstop
Air Canada Logo
9:50 am - 12:26 pm
ORD
-
YYZ
1h 36mnonstop
$198Air Canada
Thu, Apr 16 - Mon, Apr 20
Air Canada Logo
8:15 am - 9:10 am
YYZ
-
ORD
1h 55mnonstop
Air Canada Logo
4:15 pm - 6:58 pm
ORD
-
YYZ
1h 43mnonstop
$209Air Canada
Wed, Apr 1 - Tue, Apr 7
United Airlines Logo
10:15 am - 11:18 am
YYZ
-
ORD
2h 03mnonstop
United Airlines Logo
5:57 pm - 8:44 pm
ORD
-
YYZ
1h 47mnonstop
$224United Airlines
Thu, Apr 16 - Mon, Apr 20
Delta Logo
6:10 am - 12:43 pm
YYZ
-
MDW
7h 33m
1 stop
Delta Logo
2:12 pm - 11:10 pm
MDW
-
YYZ
7h 58m
1 stop
$258Delta
Thu, Apr 16 - Mon, Apr 20
Delta Logo
6:10 am - 12:43 pm
YYZ
-
MDW
7h 33m
1 stop
Delta Logo
9:29 am - 6:31 pm
MDW
-
YYZ
8h 02m
1 stop
$259Delta
Tue, Apr 7 - Tue, Apr 14
Multiple Airlines Logo
6:15 pm - 12:22 am
YTZ
-
ORD
7h 07m
1 stop
Multiple Airlines Logo
6:01 pm - 8:03 pm
ORD
-
YTZ
25h 02m
2 stops
$286Multiple Airlines
Tue, Apr 7 - Tue, Apr 14
Multiple Airlines Logo
6:15 pm - 12:22 am
YTZ
-
ORD
7h 07m
1 stop
Multiple Airlines Logo
6:01 pm - 10:25 am
ORD
-
YTZ
15h 24m
1 stop
$288Multiple Airlines
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.

How much is a round-trip flight from Toronto to Chicago?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Toronto to Chicago departing in April.

What is the cheapest Toronto to Chicago flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Toronto to Chicago costs $166 on the route between Toronto Island Airport (YTZ) and Chicago Midway Airport (MDW). Over the past month, this route was, on average, 19% cheaper than other Toronto-Chicago routes. The most popular route is between Toronto Pearson Intl Airport (YYZ) and Chicago O'Hare Intl Airport (ORD).

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 Thursday, 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 Thursday 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 July, where tickets cost $213 (return) on average. On the other hand, the most expensive months are December and January, where the average cost of round-trip tickets is $275 and $273 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.

No, with an average price for the route of $273, prices are generally cheapest when you fly direct.

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 4 weeks before departure, which saves you about 54% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.

Expert advice

Expert advice for your flight from Toronto to Chicago

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Our travel experts
Stefanie Waldek

Stefanie Waldek

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

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.

John Walton

John Walton

Expert on Porter Airlines

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.

Harriet Baskas

Harriet Baskas

Expert on American Airlines

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.

Good to know

Low seasonJanuary
Cheapest flight$123
Best time to beat the crowds but there is an average 10% increase in price.
Most popular time to fly and prices are also 4% 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 Canada
YYZ
-
ORD
Oct 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 Airlines
YYZ
-
ORD
Mar 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 $123 for a one-way ticket and $192 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, and United 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 $266 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 $152 or less one-way and $264 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 423 reviews
8.0Comfort
7.0Entertainment
8.2Boarding
8.6Crew
7.6Food
Airline reviews

The Flight took off 2hrs late because there was no pilot showing up when the flight was ready to board.. Though the cabin crew was present and had prepared the plane, the FO turned around after 15 min and went away. A crew to fly the plane finally arrived over an hour later and we were able to board 1h30 min later than planned time... until everything was loaded, we left 2h late from the gate. This was a small plane, so don't expect any Entertainment... Wi-Fi access on board would work, but took an awful amount of time to figure out and get it work (I'm an IT person). Flying as VIPorter customer, I was expecting at least some warm meal, but everything served was just cold.. except the coffee maybe. Even in so-called VIPorter seats, space is cramped and trays are so tiny, you can barely setup your food. Flight caught up during the coast-to-coast crossing and was able to recoup about 45 min from the delay.. still arrived very late in Vancouver and had to wait a long time to get our registered bags. Let's see how the return flight will be in a few days..

6.0 GoodBeat, Jan 2026
YUL - YVR
Read more Porter Airlines reviews

The Flight took off 2hrs late because there was no pilot showing up when the flight was ready to board.. Though the cabin crew was present and had prepared the plane, the FO turned around after 15 min and went away. A crew to fly the plane finally arrived over an hour later and we were able to board 1h30 min later than planned time... until everything was loaded, we left 2h late from the gate. This was a small plane, so don't expect any Entertainment... Wi-Fi access on board would work, but took an awful amount of time to figure out and get it work (I'm an IT person). Flying as VIPorter customer, I was expecting at least some warm meal, but everything served was just cold.. except the coffee maybe. Even in so-called VIPorter seats, space is cramped and trays are so tiny, you can barely setup your food. Flight caught up during the coast-to-coast crossing and was able to recoup about 45 min from the delay.. still arrived very late in Vancouver and had to wait a long time to get our registered bags. Let's see how the return flight will be in a few days..

It was okay. Had a thing with the front desk, she had me repack my suitcases to have them be under the weight restrictions, but then the other one was overweight, she argued with me about it when there were tons of people in line. Wasn’t great.

Due to a known technical error that Porter has not fixed in over a year, I was unable to check in the children on my reservation online and had to do it at the airport. Upon check in, there were no seats together, which was an issue as we had young children. The gate agent did manage to seat us together by moving other passengers, which was appreciated, but the other passengers were never informed, leading to confusion and delay upon boarding. The flight was over an hour late; no explanation or apology was ever issued. The bags on Porter take a long time to arrive--over half an hour at Hamilton on my inbound flight, and not much better on my return to Edmonton.

On my e-boarding pass it shows free wifi, yet the plane I was on didn’t have wifi. Please remove false advertising from your website and boarding passes

3.5 hr delay for a 1 hr work flight. No information as to why the delay until 20 mins before boarding.

Organization and the adjusted times but the snacks could be of a bigger portion

I like it, but the food isn't good. They need to offer more simple things. This bowls that have so many things your don't know what your are eating. The milenials like it, no the rest. And last but not least, they allowed somebody have a huge dog, vey agressive and fidgety in the flight. That's horrible. No animals should be allowed inside the airplane, what about allergies, etc

Smaller plane. Food and bar service for free is amazing. Drinks were in glass not plastic cups.

Poor landing as we overshot the runway and had to re land the plane. Lost both of my luggage not found as of yet. Had to pay extra money for my luggage in USD, now great my luggage is gone. Will not fly with Porter again.

This flight to St. Johns was really good. Boarding was a breeze. We left spot on time. Seats were actually pretty good. Recliner further than I expected. Three more flights to go we will see if this is the status quo for Porter.👍

We are a senior couple (70+) and chose emergency exit seats so we would have 2 seats together and neither of us had to sit in a middle seat. My husband is type 1 diabetic on an insulin pump and I monitor his blood sugar levels. I am 5'9" and 250 lbs and found the seats extremely uncomfortable. Toward the end of the flight I developed diarrhea which lasted a full 24 hours.

They never sent me a confirmation to say my flight time had changed so I cut my holiday short by 6 hours Had to pay over 50 American for my luggage to be checked on the way home and that’s more that it cost on the way there. Arbitrarily charging more for the same thing when the passenger has no options is shady The cabin was an icebox going there and back, if all the passengers have their gloves on and their hoods up that should be an obvious sign to turn up the heat

I was very nice to arrive earlier than scheduled. Very much appreciated. No issues with flight. All was good.

The on-board crew were professional and friendly and made the trip feel like we were taken care of well. The gate for the flight departure changed three times...not great but not terrible. Considering it was the day of the New Jalisco Cartel mayhem, we can't really complain.

We were treated well by the staff at the airport and on board aircraft. Delay was uncontrollable due to the weather. Had to wait for another gate as we were late landing in Fort Lauderdale.

I was supose to have a carrey on incluided for each passenger and they made me paid 75$ each at the gate.

Great crew and entertaining Captain. Seats were not what we had expected based on my booking but things worked out in the end. Of course, like all airlines these days not enough leg or elbow room.

The entertainment system was down; food by purchase only; several people did not receive their luggage. No one answers at the local office or online about the luggage.

I did not like I have been charged for my carry on

Onward flight was okay. return from Lisbon was poor as we missed our flight due to a long line at the passport control. Air Transat made no effort to accommodate us even though we were at the passport control 40 minutes prior to the departure.

They never clean the toilet, and the food is worse

Wonderful. Quick boarding. Early departure and we arrived 30 minutes early at our destination. Unfortunately, when you arrive early, there is still a departing aircraft at our gate. We had to park for 30 minutes until the gate was clear. So our early arrival was not really early at the gate. Otherwise it was a quick and smooth flight. Appreciated the efficiency.

Chargers didn’t work, no entertainment and we had to wait for taxiing for easily 40 minutes after arriving early. Bags were late too!

No real complaints. The in flight food was much better than I expected. The in flight entertainment was excellent.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

Horrible Flight significantly delayed. Not due to united issue. But trying to rebook connection flight and get information about overnight accommodation was difficult. Agent did not seem to care or have any interest to help.

United Airlines is my preferred airlines and I am thankful for Gary who also help support me on the phone to switch my flight literally last min.

This Japanese airline provides great service and very helpful in assisting their passengers.

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

I understand that there is a catering issue - water should be the minimum stock. During the flight, not once that the attendants came through with water. The conversations in the kitchen were very loud and they were swearing. I do not expect any white glove service, at the minimum, we should be cordial. It was almost an inconveniece that we were on the flight. And it made us feel if you even dare question us, we'll make you deplane.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

It was good experience this time. The flight was on time.

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

The gate agent had a really bad attitude and refused to help me get on the standby list. She just handed me a card and said I needed to call a number. I asked her to help with the AA app on my phone and she just shrugged and said she didnt know. After a few phone calls, I eventually just went to a different gate agent on the other side of the terminal and got the help I needed.

Overall, my last three trips on American Airlines have all been either delayed or "rescheduled" due to mechanical issues. At least on delay caused me to miss two possible connecting flights each later than the first. My last option for my last connection required the assistance of the onsite service desk (O'Hare Airport). The wait time for the service desk was such that it jeopardized getting booked on the last connecting flight available for the night. Suffice it to say, my latest experiences with American Airlines have caused me extensive loss of productive business and personal time and can therefore be classified as significantly less than satisfactory.

Waiting for gate in RDU for more than 20mins is crazy.

American Airlines was great and worked very hard to change my ticket so I could get an earlier, direct flight back to Dallas. However, I was informed that Kayak made mistakes with my itinerary and classified my ticket as desiring to be on the earlier flight instead of taking the necessary step of calling AA to get me on the standby list. This ended up keeping me from being added to the standby list and delayed me getting home by 6 hours. I am happy to discuss this further with Kayak so they can correct their procedures so this won't happen again.

Waited for oxygen tanks for 30 minutes after boarding was complete.

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

Terrible…. Reported missing luggage’s with injectable meds that needed refrigeration. Yet, delivery could not be expedited. Luggage’s were delivered 5 days after arrival. The meds were useless as ice pack had melted. So disappointed!!!

My seat was covered in vomit and I will be reaching out to Air Canada

It's kindof ridiculous that your system is even asking me about this since my flight was canceled and I wasn't rescheduled.

3 hr delay at the gate while they were doing maintenance. Next time, do not board passengers while maintenance is being performed

Digital check in is very poor with air canada compaired to other airlines

Baggage delayed we had to catch our cruise without any clothes 😒

Air Canada Rouge is great. Toronto Airport is the usual nightmare

Good but need to be better with the flight times.

The staff was great and made the long trip easy peasy!

The free Wi-fi for Aeroplan members was a great touch. The time passed quickly. I found the seats seemed a little closer together than I remember. Not Air Canada's fault, but we were about 20 minutes late landing because the airport was too busy. We had to circle around for a while. The boarding and disembarking went very smoothly.

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$8121h 50m
Buses$11716h 17m