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YTO - CHI

C$ 172 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 29/5. 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
0 bags
Fri 7/6
Fri 14/6

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These are the airlines KAYAK users have selected most often from within our search results in flight searches from Toronto to Chicago.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Toronto to Chicago.
In the last 7 days, travellers have searched 43,968,530 times on KAYAK, and here is why:

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Cheap flight deals 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 and deals for you by selecting your travel dates.
Choose your dates
6:30 a.m. - 5:40 p.m.YYZ-ORD
12h 10m1 stop
6:40 p.m. - 2:00 p.m.ORD-YYZ
18h 20m1 stop
C$ 291
Find Deal
Tue, 4 Jun - Tue, 11 Jun
6:30 a.m. - 5:40 p.m.YYZ-ORD
12h 10m1 stop
6:40 p.m. - 2:00 p.m.ORD-YYZ
18h 20m1 stop
C$ 295
Find Deal
Wed, 5 Jun - Wed, 12 Jun
8:50 p.m. - 9:37 p.m.YTZ-MDW
1h 47mdirect
8:00 a.m. - 10:42 a.m.MDW-YTZ
1h 42mdirect
C$ 298Porter Airlines
Find Deal
Fri, 24 May - Tue, 28 May
8:50 p.m. - 9:37 p.m.YTZ-MDW
1h 47mdirect
5:15 p.m. - 7:57 p.m.MDW-YTZ
1h 42mdirect
C$ 300Porter Airlines
Find Deal
Thu, 6 Jun - Thu, 13 Jun
12:00 p.m. - 12:54 p.m.YYZ-ORD
1h 54mdirect
1:00 p.m. - 3:43 p.m.ORD-YYZ
1h 43mdirect
C$ 333Air Canada
Find Deal
Wed, 22 May - Wed, 29 May
6:30 a.m. - 10:01 a.m.YYZ-ORD
4h 31m1 stop
7:10 a.m. - 9:58 a.m.ORD-YYZ
1h 48mdirect
C$ 339Air Canada
Find Deal
Thu, 23 May - Mon, 27 May
7:00 a.m. - 7:57 a.m.YYZ-ORD
1h 57mdirect
11:45 a.m. - 7:00 p.m.ORD-YYZ
6h 15m1 stop
C$ 346United Airlines
Find Deal
Sun, 2 Jun - Wed, 5 Jun
3:09 p.m. - 4:04 p.m.YYZ-ORD
1h 55mdirect
8:30 a.m. - 2:59 p.m.ORD-YYZ
5h 29m1 stop
C$ 356American Airlines
Find Deal
Fri, 7 Jun - Tue, 11 Jun
11:55 a.m. - 12:50 p.m.YYZ-ORD
1h 55mdirect
8:15 a.m. - 4:30 p.m.ORD-YYZ
7h 15m1 stop
C$ 357American Airlines
Find Deal
Wed, 19 Jun - Wed, 17 Jul
1:45 p.m. - 11:20 p.m.YYZ-ORD
10h 35m1 stop
6:00 a.m. - 8:45 a.m.ORD-YYZ
1h 45mdirect
C$ 375United Airlines
Find Deal
Wed, 5 Jun - Wed, 12 Jun

Flights from Toronto to Chicago - Travel Insights & Trends

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.

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 one-way flights from Toronto to Chicago.
Our data shows that the cheapest route for a one-way flight from Toronto to Chicago cost C$ 173 and was between Toronto Island Airport and Chicago Midway Airport. On average, the best prices are found if you fly this route. The average price for a return flight for this route is C$ 285.

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

The average price of all 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 Saturday, as we generally find the cheapest rates on that day for this route. On the other hand, Sunday is the most expensive day to fly from Toronto to Chicago. For your return ticket, we recommend flying on a Wednesday and avoiding Fridays 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 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 April, where tickets cost C$ 328 on average. On the other hand, the most expensive months are August and September, where the average cost of tickets is C$ 463 and C$ 462 respectively.

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

The average 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 C$ 204, prices are generally cheapest when you fly direct.

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

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for 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 month.
To get a below average price on the flight from Toronto to Chicago, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 37 days before departure.

Which airlines provide the cheapest flights from Toronto to Chicago?

The cheapest price for the route for each airline clicked by KAYAK users in the last 72 hours.
In the past 3 days, the cheapest one-way tickets to Chicago from Toronto were found on Porter Airlines (C$ 176) and Air Canada (C$ 196), and the lowest round-trip tickets were found on Porter Airlines (C$ 298) and Air Canada (C$ 333).

Which airlines fly most frequently between Toronto and Chicago?

Toronto and Chicago are connected by different airlines. The airlines that fly that route the most regularly are United Airlines (9 flights per day), American Airlines (6 flights per day), and Air Canada (4 flights per day).

Which airlines fly direct between Toronto and Chicago?

Airline and price data is aggregated from results in KAYAK’s search results from the last 2 weeks for flights from Toronto to Chicago.
There are 4 airlines that fly direct from Toronto to Chicago. They are: Air Canada, American Airlines, Porter Airlines and United Airlines. The cheapest price of all airlines flying this route was found with Porter Airlines at C$ 266. On average, the best prices for this route can be found at Porter Airlines.

How many flights are there between Toronto and Chicago per day?

Each day, there are between 20 and 24 nonstop flights that take off from Toronto and land in Chicago, with an average flight time of 1h 56m. The most common departure time is 7:00 a.m. and most flights take off in the morning, while the most flights land at Chicago O'Hare Intl Airport. Each week, there are 157 flights. The most frequent day of departure is Wednesday, when 15% of all weekly flights depart. The fewest flights depart on a Saturday.

Which cabin class options are there for flights between Toronto and Chicago?

The average price of flights for each cabin class for the route found by users searching on KAYAK over the last 2 weeks.
There are 4 cabin class options for the route. These are First, Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

How long does a flight from Toronto to Chicago take?

The average direct flight takes 1h 47m, covering a distance of 1,127 km.

What’s the earliest departure time from Toronto to Chicago?

Early birds can take the earliest flight from Toronto at 6:30 am and will be landing in Chicago at 7:25 am.

What’s the latest departure time from Toronto to Chicago?

If you prefer to fly at night, the latest flight from Toronto to Chicago jets off at 9:00 pm and lands at 10:04 pm.

Good to know

Low season

January

High season

August

Cheapest flight

C$ 172
Best time to beat the crowds (11% less expensive on average)
Most popular time to fly (15% more expensive on average)
Flight from Toronto Pearson Airport to Chicago O'Hare 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.

FAQs for booking flights from Toronto to Chicago

  • What are some of the ways I can get from Chicago Midway International Airport (MDW) to downtown Chicago after a flight?

    One of the quickest options is to travel on the Orange Line provided by the Chicago Transit Authority, that can take passengers from the airport to downtown Chicago in about 20 minutes, with trains leaving every 15 minutes or so throughout the day.

  • Where should I look for the rental car companies at Chicago O'Hare International Airport?

    This airport offers an impressive number of both major rental car companies and local rental car companies that all have a location right on airport property for the convenience of passengers. All of the rental car companies operate at a multi-modal facility on the airport grounds. After any flight to this airport, passengers wishing to rent a car should follow the signage to travel on the Airport Transit System that can take you from any terminal building at the airport to the multi-modal facility in no more than about five minutes.

  • 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 C$ 125 for a one-way ticket and C$ 212 for a round-trip.

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

    Toronto has 2 major airports: Toronto Island and Toronto Pearson Intl. Chicago is served by 2 airports: Chicago Midway and Chicago O'Hare Intl. You’ll usually find the cheapest deals if you fly from Toronto Island and land at Chicago Midway Airport.

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

    Air Canada, 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 Boeing 737 MAX 8 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 direct flights from Toronto to Chicago on a daily basis.

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

    The two airlines most popular with KAYAK users for flights from Toronto to Chicago are Delta and Porter Airlines. With an average price for the route of C$ 432 and an overall rating of 8.0, Delta is the most popular choice. Porter Airlines is also a great choice for the route, with an average price of C$ 390 and an overall rating of 7.5.

  • 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.

See more FAQs

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 C$ 176 or less one-way and C$ 315 or less round-trip.
  • One of the most convenient ways you can travel from downtown Toronto to the Toronto Pearson International Airport (YYZ) is to travel on the UP Express light rail service, which makes the trip from downtown to the airport about 25 minutes or so, with trains leaving roughly every 30 minutes.
  • If you plan on travelling aboard a flight from Air Canada from Toronto Pearson International Airport, this airport offers the convenience of an Air Canada Maple Leaf Lounge as well as an Air Canada Maple Leaf Lounge Express inside Terminal 1, offering plenty of food and drink options plus showers in the standard lounge.
  • Chicago O'Hare International Airport (ORD) is not only a great airport choice for those making their way to downtown Chicago, but it is also quite convenient when making a trip to towns and suburbs to the north and east of Chicago, including Rockford, Aurora, and Gurnee.
  • 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.
See more tips

Prefer to fly non-stop from Toronto to Chicago?

Find which airlines fly direct from Toronto to Chicago, which days they fly and book direct flights.

Nonstop departures

Toronto to Chicago

Monday

ANA, Air Canada, Air New Zealand, +12 more

ANA, Air Canada, +13 more

Tuesday

ANA, Air Canada, Air New Zealand, +13 more

ANA, Air Canada, +14 more

Wednesday

ANA, Air Canada, Air New Zealand, +13 more

ANA, Air Canada, +14 more

Thursday

ANA, Air Canada, Air New Zealand, +12 more

ANA, Air Canada, +13 more

Friday

ANA, Air Canada, Air New Zealand, +13 more

ANA, Air Canada, +14 more

Saturday

ANA, Air Canada, Air New Zealand, +14 more

ANA, Air Canada, +15 more

Sunday

ANA, Air Canada, Air New Zealand, +13 more

ANA, Air Canada, +14 more

See more nonstop flights

Nonstop returns

Chicago to Toronto

Monday

ANA, Air Canada, Air New Zealand, +13 more

ANA, Air Canada, +14 more

Tuesday

ANA, Air Canada, Air New Zealand, +14 more

ANA, Air Canada, +15 more

Wednesday

ANA, Air Canada, Air New Zealand, +14 more

ANA, Air Canada, +15 more

Thursday

ANA, Air Canada, Air New Zealand, +13 more

ANA, Air Canada, +14 more

Friday

ANA, Air Canada, Air New Zealand, +15 more

ANA, Air Canada, +16 more

Saturday

ANA, Air Canada, Air New Zealand, +14 more

ANA, Air Canada, +15 more

Sunday

ANA, Air Canada, Air New Zealand, +14 more

ANA, Air Canada, +15 more

See more nonstop flights
See more nonstop flights

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.
8.1
WestJet EncoreOverall score based on 51 reviews
8.7Crew
7.4Entertainment
7.6Comfort
7.3Food
8.6Boarding
Airline reviews

Great flight, comfort, and staff. Prefer tv in back of seat but watching on phone will do

10.0 ExcellentDarren, May 2023YYZ - LAX
Read more about WestJet Encore reviews

Great flight, comfort, and staff. Prefer tv in back of seat but watching on phone will do

Pros: "Friendly staff and the support they offered to my mother who needed a wheelchair."
Cons: "I would have liked to have had WestJet internet and entertainment access. It was not offered on our flight from Toronto to Fredericton."
Pros: "The fact that military personnel and retired military personnel and their spouse can check in luggage for free. The check in crew was also very courteous."
Pros: "It ran on time. The pilot landed the plane without a big jolt. We could board and deplane using 2 exits."
Cons: "Seat space"
Pros: "Rotten stuff cancels out the good doesn't it. Be great if you could take some courses from Stephen Covey as you are missing some skills sets in hospitality. And stop being so cheap with the 3rd rate old old movies!"
Cons: "I did not appreciate having the second row to the last on my 2nd plane coming back - I only had a turn around time of 20 minutes to catch my third Westjet flight. When we asked if the plane would wait for us - your crew just laughed in our faces."
Pros: "Great, friendly crew in this scenic trip across to Victoria. Nice new aircraft operating this route."
Pros: "Cheerfulness of WestJet employees."
Cons: "Seat comfort; seats hard. Person next to me average size but still spilled into my seat with “man-spreading” and shoulders."
Pros: "Efficient crew and reasonable seating"
Cons: "Need more legroom or a device to fold passenger legs for the flight duration..."
Pros: "Crew was good. Seats need to be updated and are confining. I appreciated being able to disembark through front and rear door."
Cons: "More space between the seats."
Pros: "the crew was very polite but the flight was too short to have a meal"
Cons: "delayed embarking"

Wish we had music during take off and landing like the last flight

First time with Porter and I can say this is best airline company in Canada. Great service, free WiFi, free snack and drinks (including beer and wine). Seats were super comfy on the Embraer jet and I appreciated the folding try table too. Staff were excellent both legs of the trip.

Tight transfer in Montreal. (15 min) However, we made it, as did my luggage.

Check in was slow because of passenger ahead in Reserve line. Seats were somewhat uncomfortable.

First time with Porter. Amazing experience overall, will be my airline of choice in North America whenever possible. Liked the quality of food and how it was served but one suggestion- a hot meal on the longer flights, perhaps?

Delayed by 2.5 hours. This happened previously on my flight from YOW to YVR on Dec. 26.2023. This is a terrible airline. The reason was there was lack of ground crew. This is a known event. AVOID PORTER AIRLINES IF YOU CAN. There is a reason half the plane was empty.

The airline arrival at the downtown airport is a big plus.. Food and beverage was excellent. Their non weather related cancellation is horrible. Overall I gave the airline 7 over 10 Tips for people flying porter from Boston. The airline doesn’t have inflight entertainment No TV No WIFI. Bring your entertainment with you.

The airline arrival at the downtown airport is a big plus.. Food and beverage was excellent. Their non weather related cancellation is horrible. Overall I gave the airline 7 over 10

Wasn’t on the flight- again. Bad weather in Halifax and I was in an accident. What a poor experience to have to pay for all this flight and not be on it

I didn’t make my flight due to poor weather and I had an accident driving there. I tried to get my money back or even credit and nothing. I have an entire flight both to Florida and back that I paid for and no one will give me any money back. I know this isn’t just Porter and it’s 3rd party- however airlines should allow these companies to take money for things they don’t get. I’m so upset. Who can afford a full flight they never take?

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.

Everything was great. I really like how they had their safety film set up showing you the beauty of the country.

I liked the early check in. Flight was a bit bumpy due yo weather. Overall, everything went well.

Limited snack options cause the snack vendor was on strike

It was an excellent experience, traveling from Toronto to Denver with United.

Ontime boarding. Almost 1 hour take off delay. We could have boarded slightly later since the pilots were in traffic

Flight was delayed, I had to put my luggage all the way in the back! They served only a beverage no snack on the way in Air Canada, definitely not a good first impression.

This was the first AC flight in a long time that we experienced no delays or frustrations. The gate attendant was extremely polite and accommodating to my husband who has Parkinson’s disease which made boarding extremely stress free. Flight departed ON TIME and was a smooth ride. If only all my AC experiences could be like this.

I didn’t like the fact that all the customs officers went to lunch so I was in line for 90 minutes due to where the staff directed me. We were told three very different reasons for why the plane was delayed. It was a crowded plane with difficult storage situations for the Carry On bags. The Air Canada airline staff were all very good and professional. I was so disappointed in my cheese and fruit box as the cheese had molded and the fruit wasn’t fresh so I couldn’t eat the majority of the food. This was the last meal I could find as the restaurants had closed when I got in to my destination. I think you could work on improving the food quality.

Once again my complaint is how close the seats are together. Also, the bathrooms were not very clean by the second half of the flight.

Excellent in flight service, perhaps the best we've ever had. Business class feels tired and needs improvement to compete with other airlines. The food looked good but tasted terrible. Check in was quick, the flight arrived early and our luggage was on our flight with us.

Book cheap flights from Toronto to Chicago

Recent one-way flight deals

 
Only flying one-way? Below are some of the best one-way flight deals from Toronto to Chicago found on KAYAK in the last 72 hours.
29/5Wed
1 stop
12h 10mYYZ-ORD
C$ 172
5/6Wed
1 stop
12h 10mYYZ-ORD
C$ 174
14/6Fri
directPorter Airlines
1h 47mYTZ-MDW
C$ 176
26/7Fri
directPorter Airlines
1h 47mYTZ-MDW
C$ 177
16/6Sun
directAir Canada
1h 54mYYZ-ORD
C$ 196
11/6Tue
directAir Canada
1h 57mYYZ-ORD
C$ 201
12/6Wed
directUnited Airlines
2h 02mYYZ-ORD
C$ 210
10/6Mon
1 stopUnited Airlines
12h 57mYYZ-ORD
C$ 221
7/6Fri
1 stopAmerican Airlines
6h 52mYYZ-ORD
C$ 231
22/6Sat
1 stopAmerican Airlines
6h 54mYYZ-ORD
C$ 234

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Last minute flights from Toronto to Chicago

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights from Toronto to Chicago that are departing in the next 10 days.
13/5Mon
directPorter Airlines
1h 47mYTZ-MDW
21/5Tue
directPorter Airlines
1h 42mMDW-YTZ
C$ 411
13/5Mon
multi-stop
34h 39mYYZ-ORD
21/5Tue
multi-stop
25h 20mORD-YYZ
C$ 444
12/5Sun
directAmerican Airlines
1h 56mYYZ-ORD
31/5Fri
directAmerican Airlines
1h 35mORD-YYZ
C$ 510
13/5Mon
directAir Canada
1h 59mYYZ-ORD
16/5Thu
directAir Canada
1h 45mORD-YYZ
C$ 514
13/5Mon
directAmerican Airlines
1h 55mYYZ-ORD
16/5Thu
multi-stopAmerican Airlines
4h 50mORD-YYZ
C$ 525
13/5Mon
directUnited Airlines
1h 54mYYZ-ORD
16/5Thu
directUnited Airlines
1h 48mORD-YYZ
C$ 536
13/5Mon
multi-stopAir Canada
5h 55mYTZ-ORD
21/5Tue
multi-stopAir Canada
5h 46mORD-YTZ
C$ 543
13/5Mon
directUnited Airlines
2h 04mYYZ-ORD
15/5Wed
directUnited Airlines
1h 48mORD-YYZ
C$ 566
13/5Mon
multi-stopWestJet
9h 32mYYZ-ORD
16/5Thu
multi-stopWestJet
11h 13mORD-YYZ
C$ 614
10/5Fri
multi-stopWestJet
6h 37mYYZ-MDW
18/5Sat
multi-stopWestJet
5h 14mMDW-YYZ
C$ 617

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Flights to Chicago

Return flight deals:

Chicago - Toronto

Cabin classes:

C$ 1,382
C$ 1,154
C$ 545
C$ 284