Cheapest return flights from Chicago (MDW) to Toronto (YTZ), October

10 dates in October, from $ 444. Book in one tap, or check whether to buy now or wait.

One-wayReturn
Dates, airline, and price
Dates Airline Price
17 Oct 24 Oct Porter Airlines (Canada) Ltd
Direct Flight
14 Oct 17 Oct Porter Airlines (Canada) Ltd
Direct Flight
17 Oct 18 Oct Porter Airlines (Canada) Ltd
Direct Flight
16 Oct 19 Oct Porter Airlines (Canada) Ltd
Direct Flight
15 Oct 18 Oct Porter Airlines (Canada) Ltd
Direct Flight
16 Oct 18 Oct Porter Airlines (Canada) Ltd
Direct Flight
16 Oct 24 Oct Porter Airlines (Canada) Ltd
Direct Flight
15 Oct 22 Oct Porter Airlines (Canada) Ltd
Direct Flight
14 Oct 24 Oct Porter Airlines (Canada) Ltd
Direct Flight
20 Oct 24 Oct Porter Airlines (Canada) Ltd
Direct Flight
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Deals for one-way flights from Chicago to Toronto in October.

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Updated Oct 11, 2026.

About these fares

These results come from our latest search across airlines for your currency. Prices change quickly and are not locked until you complete booking—always confirm the total and fare rules on the partner site.

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