As the closest sister city to Toronto (and the only one in America), Chicago is constantly ranked as one of the top tourist destinations in the U.S., and for very good reason. With an abundance of attractions and events, along with great food, an amazing waterfront and beautiful architecture, it’s worth the roughly eight-hour drive from Ontario to visit the Windy City this summer.
“There’s so much going on in the city of Chicago,” says Lynn Osmond, president and CEO of Choose Chicago. “Lots of festivals, music, food, sports.… We just have so much to share as a city.”
Chicago is just over an eight-hour drive from the Toronto area. Heading west on Highway 401, you’ll cross the border into Detroit from Windsor, Ont. A majority of the drive after that is through Michigan before you cross into Indiana and gain an hour before finally entering Illinois. If you want to take a break along the drive, Ann Arbor or Kalamazoo, Mich., are both excellent cities to stop in.