Cheapest return flights from Toronto to Chicago in October from 138€

AirHint found the following cheapest return flights from Toronto (YYZ) to Chicago (ORD) in October 2025 (see full year).

Return flights

29 Oct - 03 Nov Air Canada direct
16 Oct - 27 Nov Air Canada direct
08 Oct - 18 Oct Air Canada direct
31 Oct - 03 Nov Air Canada direct
30 Oct - 03 Nov Air Canada direct
24 Oct - 03 Nov Air Canada direct
31 Oct - 07 Nov Air Canada direct
24 Oct - 27 Oct Air Canada direct
17 Oct - 19 Oct Air Canada direct
16 Oct - 19 Oct Air Canada direct
03 Oct - 05 Oct Air Canada direct
03 Oct - 06 Oct Air Canada direct
04 Oct - 06 Oct Air Canada direct
23 Oct - 26 Oct Air Canada direct
20 Oct - 31 Oct Air Canada direct
16 Oct - 20 Oct Air Canada direct
30 Oct - 02 Nov United direct

Also check the deals for one-way flights from Toronto to Chicago in October.

Skyscanner

The deals are updated regularly. The prices may go up as tickets are purchased by other travellers. Only the cheapest flights are offered. Select a price to book and secure these cheap prices.

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