What’s the cost of a flight from Chicago Midway to Toronto Island?

Prices vary based on date, airline, and availability. Compare several options if you're flying between Chicago and Toronto.

Choose a date to explore the best fares now.

If possible, avoid holiday periods: ticket prices tend to rise quickly and availability drops, especially on busy routes. Morning and evening flights are often in high demand too — book early to get a good fare.

Which airports near Chicago or Toronto offer flights?

In many cases, using a nearby airport can improve your chances of finding direct flights or better rates.

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

Secondary airports can offer faster travel thanks to shorter lines and quicker boarding times than major ones.

Flight filters for the route Chicago Midway – Toronto Island

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 Canada are often searched alongside: Calgary, Montreal, Quebec, Toronto, Vancouver.

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.