Find cheap flights from Toronto to Chicago from C$ 182

• Looking for a cheap flight? 25% of our users found flights on this route for C$ 229 or less one-way and C$ 424 or less round-trip.
• The cheapest flight from Toronto to Chicago was found 89 days before departure, on average.
• Book at least 3 weeks before departure in order to get a below-average price.
• High season is considered to be February, March and April. The cheapest month to fly is June.
• Morning departure is around 7% more expensive than an evening flight, on average*.
• 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.

• 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.

• How long does a flight from Toronto to Chicago take?

  The average direct flight takes 1h 47m, covering a distance of 702 km.

• How many flights are there between Toronto and Chicago?

  In normal times, a total of 667 direct flights connect Toronto to Chicago weekly. On average, there are 95 departures per day.

• Which airlines provide the cheapest flights from Toronto to Chicago?

  In the past 3 days, the cheapest one-way tickets to Chicago from Toronto were found on Porter Airlines (C$ 244) and American Airlines (C$ 299), and the lowest round-trip tickets were found on Porter Airlines (C$ 496) and American Airlines (C$ 498).

• 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 (17 flights per day, Air Canada (15 flights per day), and American Airlines (7 flights per day).

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

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

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

  Toronto has 3 major airports: Toronto Kitchener-Waterloo, 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.

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

  The earliest flight leaves Toronto at 6:30 am and lands in Chicago at 7:20 am.

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

  The last flight leaves Toronto at 9:15 pm and lands in Chicago at 10:14 pm.

• Which airlines fly direct between Toronto and Chicago?

  All the following airlines operate direct flights between Toronto and Chicago: American Airlines, Air Canada, Alaska Airlines, Finnair, British Airways, Copa Airlines, Aer Lingus, Iberia, Japan Airlines, Egypt Air, ANA, Air New Zealand, Qantas Airways, Qatar Airways, Royal Jordanian, Scandinavian Airlines, United Airlines, and Porter Airlines.

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

  The Boeing 737-800 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$ 384 and an overall rating of 7.9, Delta is the most popular choice. Porter Airlines is also a great choice for the route, with an average price of C$ 328 and an overall rating of 7.7.

• Which airlines have a flexible cancellation policy for flights from Toronto to Chicago due to COVID-19?

  United Airlines, Air Canada and Air New Zealand have all waived their change and cancellation fees on flights from Toronto to Chicago. Confirm policies on booking site.

• 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.

Book cheap flights from Toronto to Chicago

Recent round-trip flight deals

28/6Wed

1 stopMultiple Airlines

9h 46mYYZ-ORD

3/7Mon

1 stopMultiple Airlines

7h 35mORD-YYZ

C$ 352

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21/6Wed

1 stopMultiple Airlines

9h 46mYYZ-ORD

28/6Wed

1 stopMultiple Airlines

11h 55mORD-YYZ

C$ 361

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21/6Wed

2 stopsMultiple Airlines

14h 13mYYZ-MDW

28/6Wed

1 stopMultiple Airlines

11h 30mMDW-YYZ

C$ 361

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21/6Wed

2 stopsMultiple Airlines

14h 13mYYZ-MDW

28/6Wed

1 stopMultiple Airlines

11h 30mMDW-YYZ

C$ 365

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7/7Fri

directPorter Airlines

1h 47mYTZ-MDW

14/7Fri

directPorter Airlines

1h 42mMDW-YTZ

C$ 371

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13/9Wed

directAmerican Airlines

1h 57mYYZ-ORD

5/10Thu

directAmerican Airlines

1h 45mORD-YYZ

C$ 372

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7/7Fri

directPorter Airlines

1h 47mYTZ-MDW

14/7Fri

directPorter Airlines

1h 42mMDW-YTZ

C$ 373

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22/6Thu

directAir Canada

1h 55mYYZ-ORD

28/6Wed

1 stopAir Canada

6h 50mORD-YYZ

C$ 379

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7/7Fri

directPorter Airlines

1h 47mYTZ-MDW

14/7Fri

directPorter Airlines

1h 42mMDW-YTZ

C$ 380

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21/9Thu

1 stopAmerican Airlines

5h 35mYYZ-ORD

25/9Mon

1 stopAmerican Airlines

5h 07mORD-YYZ

C$ 382

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28/6Wed

directPorter Airlines

1h 47mYTZ-MDW

3/7Mon

directPorter Airlines

1h 42mMDW-YTZ

C$ 382

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13/9Wed

directAmerican Airlines

1h 57mYYZ-ORD

5/10Thu

1 stopAmerican Airlines

8h 07mORD-YYZ

C$ 384

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30/8Wed

1 stopMultiple Airlines

8h 19mYYZ-ORD

6/9Wed

1 stopMultiple Airlines

10h 02mORD-YYZ

C$ 387

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18/9Mon

1 stopAmerican Airlines

5h 08mYYZ-ORD

24/9Sun

directAmerican Airlines

1h 46mORD-YYZ

C$ 390

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21/6Wed

directAir Canada

1h 50mYYZ-ORD

27/6Tue

1 stopAir Canada

6h 50mORD-YYZ

C$ 422

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21/6Wed

directAir Canada

1h 50mYYZ-ORD

2/7Sun

directAir Canada

1h 43mORD-YYZ

C$ 423

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21/9Thu

1 stopDelta

7h 24mYYZ-MDW

25/9Mon

1 stopDelta

7h 55mMDW-YYZ

C$ 430

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21/6Wed

directAir Canada

1h 50mYYZ-ORD

1/7Sat

1 stopAir Canada

5h 56mORD-YYZ

C$ 430

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19/7Wed

1 stopDelta

8h 42mYYZ-MDW

24/7Mon

1 stopDelta

8h 03mMDW-YYZ

C$ 458

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6/9Wed

1 stopWestJet

4h 55mYYZ-MDW

8/9Fri

1 stopWestJet

5h 11mMDW-YYZ

C$ 525

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Recent one-way flight deals

28/6Wed

1 stopMultiple Airlines

9h 46mYYZ-ORD

C$ 182

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28/6Wed

directPorter Airlines

1h 47mYTZ-MDW

C$ 182

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10/9Sun

2 stopsMultiple Airlines

25h 08mYYZ-MDW

C$ 186

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28/6Wed

directPorter Airlines

1h 47mYTZ-MDW

C$ 199

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28/6Wed

1 stopMultiple Airlines

9h 46mYYZ-ORD

C$ 202

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21/6Wed

1 stopMultiple Airlines

9h 46mYYZ-ORD

C$ 203

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29/6Thu

directPorter Airlines

1h 47mYTZ-MDW

C$ 206

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19/7Wed

1 stopMultiple Airlines

9h 06mYYZ-ORD

C$ 206

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2/7Sun

directPorter Airlines

1h 47mYTZ-MDW

C$ 210

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16/7Sun

directPorter Airlines

1h 47mYTZ-MDW

C$ 217

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13/9Wed

1 stopAmerican Airlines

5h 19mYYZ-ORD

C$ 224

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12/9Tue

1 stopAmerican Airlines

7h 28mYYZ-ORD

C$ 226

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14/9Thu

directAmerican Airlines

1h 57mYYZ-ORD

C$ 229

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22/6Thu

directAir Canada

1h 50mYYZ-ORD

C$ 238

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30/6Fri

1 stopAir Canada

6h 07mYYZ-ORD

C$ 245

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7/7Fri

directAir Canada

1h 55mYYZ-ORD

C$ 246

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21/11Tue

1 stopDelta

7h 24mYYZ-MDW

C$ 268

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4/7Tue

directUnited Airlines

1h 55mYYZ-ORD

C$ 274

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23/6Fri

1 stopUnited Airlines

13h 46mYYZ-ORD

C$ 285

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31/8Thu

1 stopWestJet

6h 01mYYZ-MDW

C$ 305

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