Open interactive map ->Cheap flights from Chicago to Canada
Looking to fly from Chicago to Canada? We're tracking 7 Canadian destinations with live prices — recent fares have started from €84 to Toronto. Use the interactive map to see every option at once instead of searching city by city.
Popular destinations in Canada from Chicago
The most popular Canadian destinations from Chicago include Toronto, Vancouver, Montreal, Quebec and Calgary. Prices vary by season, airline, and how far in advance you book. Use the interactive map below to compare all available Canadian routes from Chicago and find the cheapest option for your dates.
Cheapest destinations from Chicago
Other destinations from Chicago
Flights to Canada from nearby airports
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Frequently asked questions
How many destinations in Canada can I fly to from Chicago?
SkyHopp currently tracks 7 destinations in Canada from Chicago Airport (ORD). Prices are refreshed regularly as our flight partners publish new fares.
What is the cheapest flight from Chicago to Canada?
Recent fares from Chicago to Canada have started from €84 to Toronto. Prices change frequently — check the table above for the latest available fares.
Are there direct flights from Chicago to Canada?
Some routes from Chicago to Canada may be direct, while others include a connection. Use the "Direct only" filter on the interactive map to show non-stop options only.
When is the cheapest time to fly from Chicago to Canada?
Shoulder-season months and mid-week departures typically offer the lowest fares. Check the month-by-month price calendar on each route page to find the cheapest window.