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

Return flights

27 Sep - 30 Sep	Scandinavian Airlines
22 Sep - 25 Sep	Frontier Airlines
27 Sep - 04 Oct	Spirit Airlines
22 Sep - 26 Sep	Frontier Airlines
26 Sep - 29 Sep	Frontier Airlines
21 Sep - 11 Oct	Lufthansa
25 Sep - 29 Sep	Frontier Airlines
15 Sep - 18 Sep	TAP
26 Sep - 26 Oct	Turkish Airlines
18 Sep - 25 Sep	Scandinavian Airlines
15 Sep - 06 Oct	TAP
14 Sep - 30 Sep	Frontier Airlines
19 Sep - 11 Oct	Frontier Airlines
26 Sep - 26 Oct	United	direct
20 Sep - 27 Sep	United	direct
26 Sep - 29 Sep	United	direct
15 Sep - 06 Oct	United	direct
18 Sep - 01 Oct	United

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

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 September from 534€

Return flights