Search flights from Toronto (YTO) to Chicago (CHI)

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Cheapest flights to Chicago

The cheapest flights available in the next 60 days – prices are updated regularly

Thu 13 Nov
US$172.35
One way
Economy
1 traveller
Wed 5 Nov
US$172.92
One way
Economy
1 traveller
Wed 12 Nov
US$174.17
One way
Economy
1 traveller

Flying from Toronto to Chicago: things to know

The most popular route is from Billy Bishop Toronto City Airport in Toronto to Midway International Airport in Chicago. On average this flight takes 1 hour 49 minutes one way and costs US$386 for the round trip.

Most popular route
Billy Bishop Toronto City Airport (YTZ) to Midway International Airport (MDW)
Average flight time
1 hour 49 minutes
Average round-trip price
US$386
Fly from Toronto to Chicago
10 airlines

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Airlines that fly from Toronto to Chicago

Airline options may vary according to recently booked flights and your search terms

  • Porter Airlines
  • Air Canada
  • United Airlines
  • American Airlines
  • Air Transat
  • Japan Airlines
  • All Nippon Airways
  • Flair Airlines
  • British Airways
  • Aer Lingus

Frequently asked questions

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Flights from Toronto to the United States

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Flights to Illinois

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Flights to Chicago O'Hare International Airport

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Flights to Midway International Airport

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Flights from Canada to the United States

More options to fly to the United States.

Hotels in Chicago

A popular choice with visitors to the United States.

All flights

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