How much is a flight from Toronto Island to Chicago Midway?

There’s no fixed price — fares between Toronto and Chicago can vary a lot by day or time.

Can$108 is the lowest fare found in the past 15 days.

Flying during the week can be more affordable, as weekend flights tend to be pricier. Also consider demand and availability: the last remaining seats often come at higher fares!

Planning flights between Toronto and Chicago? Don’t forget the airport options

Especially when flying to medium or large cities, it's worth checking all possible airport combinations before booking.

• Airports in Toronto: 4 airports are listed in Toronto - John C. Munro, Kitchener Lake, Lester B. Pearson, Toronto Island Airport.
• Airports in Chicago: Chicago features 3 airports - Midway, O'Hare, Rockford.

Check for differences in transport costs to and from each airport — they affect your total spend. Choosing the right airport can make a real difference in price and timing.

Flight filters for the route Toronto Island – Chicago Midway

Customize your search on Jetcost to focus only on flights that suit your needs. Whether you want a direct connection, specific airline, or shorter layover, filters help you find it faster.

Other popular destinations

Flights to United States are often searched alongside: Atlanta, Los Angeles, Miami, New York City, Orlando.

The cheapest flights might leave at odd hours or arrive at less central airports — keep that in mind. If you travel often, you can always select your trusted airlines from the available options.