Cheapest return flights from Chicago (MDW) to Toronto (YYZ)

Cheapest month: December 2026, from $ 327. Book in one tap, or open a month for every date.

All destinations from Chicago (MDW)

One-wayReturn

  • October 2026

    29 Oct – 1 Nov 3 nights
    $ 349 return
    Delta
    Price seen 9 Oct
    October dates

  • December 2026

    16 Dec – 11 Jan 2027 26 nights
    $ 327 return Cheapest month
    Frontier Airlines
    Price seen 9 Oct
    December dates

  • May 2027

    28 May – 7 Jun 2027 10 nights
    $ 817 return
    Delta
    Price seen 9 Oct
    May dates
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Updated Oct 9, 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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