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

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.

What are the airport options between Chicago and Toronto?

If both departure and destination cities offer multiple airports, comparing them can help you save time and money.

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

Some airports have different terminals for low-cost and traditional airlines — knowing in advance can save time. You can filter results to see only the airports that suit you.

Flight filters for the route Chicago Midway – Toronto Pearson

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, Halifax, Montreal, 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.