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Book Flights from Toronto to Chicago

Find great value on flights from Toronto to Chicago with CheapOair! Plan a vacation to Chicago and savour breath-taking view of its skyline from Sears Tower which is the tallest building in North America and boasts of wonderful architecture. Enjoy the exotic wildlife at Lincoln Park Zoo and also take out time for Shedd Aquarium which is home to rare marine species including dolphins. Taste delicious American and Asian cuisines at restaurants in Greektown or explore Lincoln Square to enjoy rare collection of wines. Whatever type of vacation you are looking for, CheapOair will help you save big on flights to Chicago!

Frequently Asked Questions - Toronto to Chicago Flights

  • When does the first flight of the day depart from YTO?

    8:30AM United Airlines Flight #8551

  • When does the last flight depart to CHI?

    9:18PM United Airlines Flight #8650

  • What is the travel distance between Toronto and Chicago?

    437 miles

  • What is the price range for flights from YTO to CHI?

    C$255 - C$255

  • How many weekly flights are there between YTO to CHI?

    There are 70 weekly flights between YTO and CHI.

  • How many daily flights fly between Toronto and Chicago?

    There are 9 daily flights between YTO and CHI

  • Which is the busiest day in terms of passengers traffic between YTO to CHI?


  • In last 30 days, what %age of CHI visitors spent less than 3 days in the city?

    50.00 %

  • Which is the nearest airport to Chicago, Illinois?

    Midway International Airport

  • Which is the nearest airport to Toronto, Canada?

    Billy Bishop Toronto City Airport

  • What’s the cost of the cheapest return flight from YTO to CHI?