Flights from Chicago to Milan

Discover amazing deals on round trip flights from Chicago to Milan. Search, compare, and book the best fares today.

Milan Italy

Flights from Chicago to Milan

The Chicago to Milan route connects the Windy City with Italy's fashion and design capital. With multiple departures from Chicago O'Hare International Airport (ORD) to Milan Malpensa (MXP), you'll find plenty of options to explore northern Italy's cultural hub.

Pro Tip: Book 6-8 weeks in advance for the best fares. Midweek departures (Tuesday-Thursday) often offer significant savings!

Direct flights available from ORD to MXP
Flight time: 9-10 hours
Best time to visit: April to June, September to October
Round trip from: $549

Popular Hotels in Milan

Handpicked accommodations for an unforgettable Milan experience

Hotel in Milan

Armani Hotel Milano

Milan, Via Manzoni

Sophisticated design hotel in the heart of Milan's fashion district

From $380/night

Four Seasons Milan

Four Seasons Hotel Milano

Milan, Via Gesù

15th-century convent turned luxury hotel in the fashion quadrilateral

From $650/night

Mandarin Oriental Milan

Mandarin Oriental Milan

Milan, Via Andegari

Elegant boutique hotel with award-winning spa near La Scala

From $520/night

Search All Milan Hotels

Create Your Custom-Made Journey Through Italy

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Where do you want to visit?

Select as many options as you like

Milan Centro

Milan Centro

Fashion capital with the iconic Duomo and La Scala opera

Lake Como

Lake Como

Stunning alpine lake with luxury villas and picturesque villages

Bergamo

Bergamo

Medieval hilltop city with Venetian walls and old town charm

Verona

Verona

City of Romeo and Juliet with ancient Roman amphitheater

Turin

Turin

Elegant city with royal palaces and the Shroud of Turin

Cinque Terre

Cinque Terre

Five colorful coastal villages with stunning hiking trails

Which type of activities do you enjoy?

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Fashion Shopping

Fashion & Shopping

World-class designer boutiques and fashion houses

Art Culture

Art & Culture

The Last Supper, museums and Renaissance masterpieces

Italian Food

Italian Cuisine

Risotto, ossobuco and authentic Milanese gastronomy

Wine

Wine Tasting

Lombardy wines, Franciacorta and vineyard tours

Lakes

Lakes & Nature

Como, Garda, Maggiore and alpine landscapes

Opera

Opera & Music

La Scala and world-renowned performances

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Or call us directly at 1-214-227-6700

Airlines Flying Chicago to Milan

Choose from top carriers for your journey

ITA Airways

ITA Airways

American Airlines

American Airlines

Lufthansa

Lufthansa

Air France

Air France

Swiss

Swiss

Other Italy Routes from Chicago

Pro Tip: Consider flying into Milan and out of Rome (or vice versa) to see more of Italy without backtracking.

To Rome

Chicago to Rome

From Miami

From New York

From Los Angeles