Cheapest one-way flights from Chicago to Milano in May from $304

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

AirHint found the following cheapest one-way flights from Chicago (MDW) to Milano (MXP) in May 2025 (see full year).

One-Way flights

28 May Porter Airlines (Canada) Ltd
31 May Porter Airlines (Canada) Ltd
30 May Porter Airlines (Canada) Ltd
17 May Porter Airlines (Canada) Ltd
21 May Porter Airlines (Canada) Ltd
16 May Porter Airlines (Canada) Ltd
19 May Frontier Airlines
02 May Porter Airlines (Canada) Ltd
03 May Porter Airlines (Canada) Ltd
06 May Delta

Also check the deals for return flights from Chicago to Milano in May.

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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