Flights from Chicago to Italy available from USD 405*

Visit Rome

With its ancient heritage, iconic landmarks and signature cuisine, Rome is a destination that gives visitors a real flavor of what Italy has to offer.

From the Colosseum to the Pantheon, there are many ancient sites to visit where you can step back in time and learn more about the city’s rich history. There are also plenty of galleries and museums, and you can even pay a visit to Vatican City, the home of the Catholic Church. Once you’ve had your culture fix, take a stroll through one of the city’s beautiful piazzas or markets to get a sense of daily life.

And of course, no trip to Rome is complete without sampling some of Italy’s traditional dishes. Don’t forget to try the carbonara and cacio e pepe, two pasta dishes that originated in the capital.

Visit Milan

Sleek and stylish, Milan is one of the world’s fashion capitals and is a destination full of European charm.

For those interested in Milan’s luxury shopping scene, head to the Galleria Vittorio Emanuele II, lined with designer stores and high-end retailers. Or explore the Brera district for more independent boutiques, perfect for picking up a souvenir or two. But Milan isn’t all style over substance! It’s also home to plenty of cultural highlights, like the Duomo cathedral and the Basilica di Santa Maria delle Grazie, where you can see Leonardo Da Vinci’s ‘The Last Supper’.

And when the evening rolls around, head over to Navigli, where bars and restaurants line the canals, and take part in the Italian tradition of aperitivo - pre-dinner drinks and snacks with friends to unwind from the day.

Fly in comfort

For the best fares and an unparalleled flying experience, choose Icelandair for your flights to Italy from Chicago. When you fly to the Europe with Icelandair, you can travel in comfort, with everything you need for an enjoyable and relaxing journey. Choose from a range of movies and music with our in-flight entertainment system, stay connected with Wi-Fi access on most flights, and you’ll even find a USB power port at every seat to power up your laptop or smartphone.

Add a stopover in Iceland to your journey

Whether it’s your first time heading to Europe or you’ve already explored a bit, why not add another destination to your trip? When you fly from Chicago to Italy with Icelandair, you can add a stopover in Iceland at no additional airfare. Take some time to get to know our island for anywhere from 1 to 7 days and then continue your journey. Explore Iceland's natural wonders along the Golden Circle route, or enjoy the culture and charm of Reykjavik with a walking tour of the capital.