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

Return flights

19 Oct - 08 Nov	TAP
29 Oct - 22 Nov	TAP
21 Oct - 30 Oct	Scandinavian Airlines
25 Oct - 28 Oct	Scandinavian Airlines
14 Oct - 11 Nov	Spirit Airlines
07 Oct - 13 Oct	Austrian Airlines
06 Oct - 20 Oct	SWISS
02 Oct - 07 Oct	Spirit Airlines
12 Oct - 14 Oct	TAP
05 Oct - 19 Oct	Austrian Airlines
02 Oct - 25 Oct	Spirit Airlines
07 Oct - 19 Oct	Scandinavian Airlines
06 Oct - 19 Oct	Scandinavian Airlines
19 Oct - 04 Nov	United
28 Oct - 04 Nov	United	direct
27 Oct - 11 Nov	British Airways
15 Oct - 03 Nov	United	direct

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

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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Cheapest return flights from Chicago to Milano in October from 340€

Return flights