AirHint found the following cheapest return flights from Chicago (ORD) to Milano (MXP) in May 2026 (see full year).

Return flights

03 May - 15 May	TAP
14 May - 21 May	Icelandair
10 May - 17 May	TAP
07 May - 14 May	Scandinavian Airlines
08 May - 22 May	TAP
22 May - 26 May	Scandinavian Airlines
19 May - 31 May	Scandinavian Airlines
23 May - 02 Jun	Scandinavian Airlines
20 May - 29 May	Icelandair
25 May - 20 Jun	Scandinavian Airlines
29 May - 05 Jun	Icelandair
24 May - 27 May	Scandinavian Airlines
31 May - 06 Jun	Icelandair
24 May - 31 May	Icelandair
25 May - 20 Jun	Lufthansa	direct
31 May - 06 Jun	Lufthansa	direct

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

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 May from $378

Return flights