Cheap flights from Chicago to Milan
The lowest fare found is €305. The cheapest month to fly is October.
Search live pricesSearch round-trip pricesLowest price by month
| October | €305 |
| December | €370 |
| July | €401 |
When is the cheapest time to fly from Chicago to Milan?
Fares are typically lowest in October, starting from €305.
Popular routes
- Chicago → Helsinki
- Chicago → Geneva
- Chicago → Berlin
- Chicago → Hamburg
- Chicago → Cologne
- Chicago → Stuttgart
- Chicago → Malaga
- Chicago → Alicante
- Chicago → Valencia
- Chicago → Seville
- Chicago → Edinburgh
- Chicago → Birmingham
Prices updated 2026-09-08