We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
Browse Airline Reviews
Before you book your next flight, see reviews from travellers around the world
Read Reviews

Low fares for Toronto (YTO) to Chicago (CHI) Low fares for Toronto to Chicago
Fri 29/09 - Sun 01/10
2 days, 0 stops max
£183
Fri 24/11 - Thu 30/11
6 days, 0 stops max
£175
Thu 21/09 - Mon 25/09
4 days, 0 stops max
£175
Wed 13/09 - Sun 17/09
4 days, 0 stops max
£183
Fri 08/09 - Thu 14/09
6 days, 0 stops max
£207
Tue 22/08 - Fri 25/08
3 days, 0 stops max
£329
Mon 21/08 - Tue 22/08
1 day, 0 stops max
£329
About TripAdvisor Flights

Your one-stop shop for finding the best flights from Toronto to Chicago. Simply tell us where and when you want to travel and we'll do all the legwork for you. Featuring the most powerful shopping tools on the web, we search the largest online travel websites, established airfare discounters, plus the world's leading airlines and low-cost carriers to bring back thousands of flight options.

Travel information for Toronto, Canada to Chicago

Route information
  • Toronto, Canada is 447 miles from Chicago
  • There are 70 daily flights from Toronto, Canada to Chicago
  • There are 83 weekly flights from Toronto, Canada to Chicago
  • 62 non-stop flights are operating from Toronto, Canada to Chicago today
  • Air Canada has the most nonstop flights between Toronto, Canada and Chicago
  • London, United Kingdom - Heathrow Airport is the most popular connection for one stop flights between Toronto, Canada and Chicago
In-Flight Information
  • The average flying time for a direct flight from Toronto, Canada to Chicago is 1 hour 50 minutes
  • Most direct flights leave around 8:16 EDT
Arrival information
  • Chicago is 9 mi from Midway Airport (Chicago, IL).
  • Midway Airport (Chicago, IL)
    • Right now, 10 airlines operate out of Midway Airport.
    • Midway Airport offers nonstop flights to 75 cities.
    • Every week, at least 1,736 domestic flights and 74 international flights depart from Midway Airport.
  • Chicago is 16 mi from O'Hare Intl Airport (Chicago, IL).
  • O'Hare Intl Airport (Chicago, IL)
    • Right now, 81 airlines operate out of O'Hare Intl Airport.
    • O'Hare Intl Airport offers nonstop flights to 217 cities.
    • Every week, at least 21,160 domestic flights and 2,267 international flights depart from O'Hare Intl Airport.

Shop for hotels in Chicago