Cheapest return flights from Toronto to Chicago in October from 127€

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

Return flights

26 Oct - 01 Nov Air Canada direct
03 Oct - 05 Oct Air Canada direct
14 Oct - 17 Oct Air Canada direct
19 Oct - 01 Nov United direct
31 Oct - 03 Nov United direct
21 Oct - 23 Oct Air Canada direct
17 Oct - 19 Oct United direct
09 Oct - 14 Oct United direct
11 Oct - 12 Oct Air Canada direct
08 Oct - 19 Oct United direct
26 Oct - 27 Oct Air Canada direct
19 Oct - 31 Oct Air Canada direct
23 Oct - 29 Oct Air Canada 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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