Cheapest return flights from Chicago to Milano in September from $1161

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

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

Return flights

30 Sep - 07 Oct KLM
23 Sep - 02 Oct KLM
01 Sep - 10 Sep Delta
22 Sep - 06 Oct Delta
14 Sep - 28 Sep Air France
01 Sep - 08 Sep Delta
07 Sep - 22 Sep Delta
11 Sep - 18 Sep Delta
29 Sep - 11 Oct Air France
10 Sep - 15 Sep Delta
11 Sep - 17 Sep Delta
25 Sep - 04 Oct KLM
13 Sep - 04 Oct KLM
12 Sep - 22 Sep KLM

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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