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Cheap flights from Chicago to Italy

Looking to fly from Chicago to Italy? We're tracking 8 Italian destinations with live prices — recent fares have started from €272 to Bologna. Use the interactive map to see every option at once instead of searching city by city.

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Popular destinations in Italy from Chicago

The most popular Italian destinations from Chicago include Bologna, Rome, Milan, Palermo and Venice. Prices vary by season, airline, and how far in advance you book. Use the interactive map below to compare all available Italian routes from Chicago and find the cheapest option for your dates.

Cheapest destinations from Chicago

  1. BolognaItaly
    FI·13h 40m·3 stops
    €272
  2. RomeItaly
    B6·10h 19m·1 stop
    €272
  3. MilanItaly
    FI·11h 15m·2 stops
    €302
  4. PalermoItaly
    FI·13h 15m·3 stops
    €341
  5. VeniceItaly
    FI·11h 15m·2 stops
    €369
  6. FlorenceItaly
    LX·9h 55m·1 stop
    €447
  7. NaplesItaly
    LX·13h 15m·2 stops
    €483
  8. GenoaItaly
    B6·12h 39m·3 stops
    €616

Other destinations from Chicago

  • Chicago to Germany
  • Chicago to France
  • Chicago to Spain
  • Chicago to Greece
  • Chicago to Netherlands
  • Chicago to United Kingdom
  • Chicago to Turkey
  • Chicago to Austria

Flights to Italy from nearby airports

  • New York to Italy
  • Newark to Italy
  • New York to Italy
  • Boston to Italy
  • Washington to Italy
  • Miami to Italy

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Frequently asked questions

How many destinations in Italy can I fly to from Chicago?+
SkyHopp currently tracks 8 destinations in Italy from Chicago Airport (ORD). Prices are refreshed regularly as our flight partners publish new fares.
What is the cheapest flight from Chicago to Italy?+
Recent fares from Chicago to Italy have started from €272 to Bologna. Prices change frequently — check the table above for the latest available fares.
Are there direct flights from Chicago to Italy?+
Some routes from Chicago to Italy may be direct, while others include a connection. Use the "Direct only" filter on the interactive map to show non-stop options only.
When is the cheapest time to fly from Chicago to Italy?+
Shoulder-season months and mid-week departures typically offer the lowest fares. Check the month-by-month price calendar on each route page to find the cheapest window.
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