Flights from Toronto to Chicago

Cheap YYZ to Chicago flights

Book your YYZ to MDW flights with Expedia and find last-minute Toronto to Chicago airfare. Expedia offers discount airfare on multiple airline carriers that fly direct and indirect routes between YYZ and MDW, with new flight deals and promotions almost daily. When you book your next trip from Pearson Intl. to Midway Intl. with Expedia, you can rest assured you’re getting great ticket prices and excellent service from one of the world’s most trusted travel providers.

Discount flights from Toronto to Chicago airfare

Browse the best deals on flights from YYZ to MDW. Deals are based on recent deals found by other Expedia users like you. Pricing may have changed for individual airlines. Expand the list to see all available flight deals from YYZ to MDW.
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Last Minute Toronto Flight Deals

Traveling on short notice? Expedia offers great deals on last-minute flights from Toronto Airport to the most popular destinations. Deals are based on recent prices found by other Expedia users within the last 12 hours. Prices change often for individual airlines, so check back regularly!
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Toronto, Ontario (YYZ) to Chicago, Illinois (MDW)

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Prices are:

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Popular Flights from Toronto, Ontario

Browse popular flight destinations from Toronto (YYZ), and plan your next exciting trip. Expedia has cheap flights from Toronto on multiple airline carriers, so book your next trip today!

Top Toronto Flights to US Destinations

Toronto to Chicago (YYZ - ORD)
Toronto to New York (YYZ - JFK)
Toronto to Denver (YYZ - DEN)
Toronto to Atlanta (YYZ - ATL)
Toronto to Miami (YYZ - MIA)
Toronto to San Francisco (YYZ - SFO)
Toronto to Los Angeles (YYZ - LAX)
Toronto to Las Vegas (YYZ - LAS)
Toronto to Houston (YYZ - IAH)
Toronto to Newark (YYZ - EWR)

Top Toronto International Destinations

Toronto to Chicago (YYZ - ORD)
Toronto to London (YYZ - LHR)
Toronto to New York (YYZ - JFK)
Toronto to Denver (YYZ - DEN)
Toronto to Paris (YYZ - CDG)
Toronto to Atlanta (YYZ - ATL)
Toronto to Miami (YYZ - MIA)
Toronto to San Francisco (YYZ - SFO)
Toronto to Los Angeles (YYZ - LAX)
Toronto to Amsterdam (YYZ - AMS)

Popular Flights from Chicago, Illinois

Browse popular flight destinations from Chicago (MDW), and plan your next exciting trip. Expedia has cheap flights from Chicago on multiple airline carriers, so book your next trip today!

Top Chicago Flights to US Destinations

Chicago to Chicago (MDW - ORD)
Chicago to New York (MDW - JFK)
Chicago to Denver (MDW - DEN)
Chicago to Atlanta (MDW - ATL)
Chicago to San Francisco (MDW - SFO)
Chicago to Miami (MDW - MIA)
Chicago to Los Angeles (MDW - LAX)
Chicago to Las Vegas (MDW - LAS)
Chicago to Houston (MDW - IAH)
Chicago to Newark (MDW - EWR)

Top Chicago International Destinations

Chicago to London (MDW - LHR)
Chicago to Paris (MDW - CDG)
Chicago to Amsterdam (MDW - AMS)
Chicago to London (MDW - LGW)
Chicago to Barcelona (MDW - BCN)
Chicago to Dubai (MDW - DXB)
Chicago to Rome (MDW - FCO)
Chicago to Hong Kong (MDW - HKG)
Chicago to Toronto (MDW - YYZ)
Chicago to Frankfurt (MDW - FRA)

YYZ to MDW Route Map

Toronto to Chicago Flights, Stats and Airplanes

Route information for flights from Pearson Intl. to Midway Intl..

Origin:
YYZ - Pearson Intl.
Destination:
MDW - Midway Intl.
Distance:
432.18 miles

YYZ - Pearson Intl. Airlines

Browse the the most popular airlines servicing the Toronto (YYZ) airport. Visit their flights pages to learn more about the most popular routes these carriers fly.

Air Canada
WestJet
United Airlines
American Airlines
Delta Air Lines

MDW - Midway Intl. Airlines

Browse the most popular airlines servicing the Chicago (MDW) airport. Visit their flights pages to learn more about the most popular routes these carriers fly.

AirTran Airways
Delta Air Lines
Frontier Airlines

Interesting Facts About Flights from Toronto to Chicago (YYZ to MDW)

  • The largest aircraft servicing flights between Toronto and Chicago from UNITED is the A320-1/2 built by Airbus Industrie with 138 seats.
  • UNITED carried a total of 53 passengers from YYZ to MDW in 2009.
  • 270 seats were available on flights from YYZ to MDW in 2009. Of those seats, a total of 149 passengers flew on all flights from YYZ to MDW that year.
  • The oldest aircraft servicing trips from Toronto, Canada to Chicago, IL in 2009 was Air Canada's A320-1/2 from Airbus Industrie which started flying in 1990.
  • The newest aircraft servicing YYZ to MDW in 2009 was Air Canada's A320-1/2 from Airbus Industrie. The A320-1/2 started flying in 1990.
  • The smallest aircraft servicing flights from YYZ to MDW for Air Canada is the A320-1/2 built by Airbus Industrie with 64 seats.
  • Air Canada operated flights from YYZ to MDW using one type of aircraft in 2009.
  • There were 149 passengers that flew from Toronto to Chicago in 2009.
  • In 2009, there were 3 airline companies operating between Toronto and Chicago.
  • The average aircraft occupancy on flights from Toronto to Chicago in 2009 was 61.27%.
  • UNITED, Air Greenland, Air Canada offer flights from Toronto, Canada to Chicago, IL.

(Source: FAA & BTS 2009 Databases)