Cheap flights from Chicago to Italy
Travel > Europe > Italy
Travel tip: If you visit Venice, make a walk through all the small streets. And also take a look over the Marcus Place in the center.Check our current prices for flights from Chicago to Italy. Please note that we also give you historical search data for this city connection. These are all airfares that people found in the past, in order to find more current flight information from Chicago to Italy, you will need to run a search below.
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Cheap Milan airfares from $1104/RT are provided by Cheapoair.com. Outbound flight is leaving on 06/27/2025, 07:15 pm from Chicago O`hare (ORD) airport and arrives at Milan Malpensa (MXP) at 08:05 pm. The flight time is 0 hours and 50 minutes. The Returning flight departes on 07/07/2025, 08:05 pm (other return dates are also available). Date posted: 08 Jan 2025
Price evolution for flights From Chicago To Italy

Recent Deals on Flights from Chicago to Italy:Roundtrip / Oneway
- $1104
Sas Scandinavian Airlines
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Milan, IT (MXP) 06/27/2025 07:15 pm Milan, IT (MXP) Chicago, IL (ORD) 07/07/2025 08:05 pm - $1120
Tap Airways
cheapoair.com check priceFrom To Departure Time Chicago, IL (ORD) Milan, IT (MXP) 06/27/2025 06:00 pm Milan, IT (MXP) Chicago, IL (ORD) 07/07/2025 05:55 am - We are sorry but currently there are no oneway offers for flights from Chicago to Italy.
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Know what to do when flying to Italy?
Venice Travel Guide Many of you must have seen a few cities and liked them, but have you ever fell in love with any of them the minute you saw them? I have! It’s called VENICE! It’s the most spectacular city, full of glamour, charm, romance...THE QUEEN [...]Venice History History states that the city Venice was built way back in AD 452, when Italy was invaded by Teutonic tribes. With this invasion, all the people of north Italy were forced to take cover on the many islands of its lagoon. It was later in the year [...]
Venice Sightseeing A paradise of gondolas, glittering canals, museums and churches -- what more could a tourist ask for? The floating city is certainly a unique holiday experience that treats you to special marvels that will leave you wanting more and more. [...]
Venice Nightlife Venice, Italy is considered to be one of the most beautiful cities in the world. The city has got several pet names like ‘City of Light’, ‘City of Bridges’, ‘City of Water’, ‘Queen of the Adriatic’, ‘La Dominante’, and [...]