Cheapest return flights from Chicago to Milano in September from $443

Best time to book flights for Chicago (ORD) to Milano (MXP) flights at AirHint

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

Return flights

29 Sep - 13 Oct Scandinavian Airlines
21 Sep - 01 Oct Turkish Airlines
17 Sep - 21 Sep Turkish Airlines
25 Sep - 22 Oct TAP
26 Sep - 22 Oct TAP
26 Sep - 23 Oct TAP
26 Sep - 24 Oct TAP
26 Sep - 28 Oct TAP
19 Sep - 05 Oct Turkish Airlines
26 Sep - 25 Oct TAP
26 Sep - 26 Oct TAP
06 Sep - 13 Sep Scandinavian Airlines
06 Sep - 13 Sep United direct
17 Sep - 21 Sep United direct

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

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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