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Top Deals on Flights to Chicago from € 336

Best fares for your destination

Milan (MIL) - Chicago (CHI)

Departure 12/12/2020
Return 22/12/2020

Rome (FCO) - Chicago (ORD)

Departure 20/12/2020
Return 05/01/2021

Catania (CTA) - Chicago (CHI)

Departure 02/11/2020
Return 08/11/2020

Rome (FCO) - Chicago (CHI)

Departure 05/12/2020
Return 09/12/2020

Palermo (PMO) - Chicago (CHI)

Departure 04/12/2020
Return 13/12/2020

Verona (VRN) - Chicago (ORD)

Departure 18/12/2020
Return 02/01/2021

Traveling to Chicago (ORD)


A picture-perfect skyline, full of skyscrapers, neon signs and cars that travel endlessly along its lengthy streets, immortalised in night photography as sparkling strips of light. This is Chicago, city of the blues, as depicted by John Landis in the cult classic The Blues Brothers, the movie featuring John Belushi and Dan Aykroyd. It's also the place where musicians such as Muddy Waters and Buddy Guy shot to fame. The Illinois city also has another quality: it is the city of departure for the famous Route 66, the road that symbolises the American myth.

By taking a flight to Chicago you can fully immerse yourself in the American way of life: visit neighbourhoods like the Loop, with its architectural gems such as Millennium Park, admire the city from the top of spectacular skyscrapers like the Willis Tower, with its 110 floors, and enjoy a blues show in one of its incredible bars. In the third biggest city in the United States after New York and Los Angeles, you'll never get bored. Here are a few of the things that you can do and see during a trip to Chicago.


An architectural gem in the middle of the Loop neighbourhood, the centre of Chicago, Millennium Park hosts masterpieces such as the majestic silver Jay Pritzker Pavilion, where you can also attend numerous free concerts, Cloud Gate, which is nicknamed The Bean by residents for its distinctive shape, and the futuristic Crown Fountain. Crossing BP Bridge, which connects the park to the Daley Bicentennial Plaza along Columbus Drive, you can admire the incredible skyline of the city as it reflects on Lake Michigan.

The shopping street, renamed the Magnificent Mile by locals. On its sides you will find more than 400 shops, from high fashion boutiques to temples of high-tech. The road has become one of the symbols of the city, thanks in part to the presence of some major skyscrapers, including the Wrigley Building – whose distinctive form was inspired by the Catedral de Sevilla – the Water Tower and the John Hancock Tower. Along Michigan Avenue you will also find the splendid Art Institute, another must. Its endless rooms contain masterpieces from artists such as Monet, Chagall, Dalì, Picasso, Manet, Warhol and also Edward Hopper, including his famous Nightwalks painting.

The famous black skyscraper with two antennas on the roof, an icon of Chicago that offers a spectacular panoramic view of the city thanks to its height of 1,450 meters and 110 floors. Catapulted up by an extremely fast lift to the 103rd floor, the doors open onto the Skydeck, where on a clear day you can see the four states, offering a complete view of Illinois, Indiana, Wisconsin and Michigan. Assuming you don't suffer from a fear of heights, the Ledge is a breathtaking experience: two glass cubes that extend out for more than a meter to give you a view of the city through the transparent floor beneath your feet. Given the height, this is a once-in-a-lifetime experience. When it was first opened in 1973, the Sears Tower, as it was then known, was the tallest skyscraper in the world, and was only overtaken in height in 1998 by the Petronas Twin Towers in Kuala Lumpur and then the new One World Trade Center, which is today the highest building in the whole of the United States.

This building rivals the Willis Tower for the best view in the city. It may be lower in height, but it arguably has a better position as it provides you with an excellent view of Lake Michigan that is particularly stunning at sunset. While the Willis Tower has the Ledge as a breathtaking observation point, at 360° Chicago, the name of the observatory on the 94th floor, you will find the spectacular Tilt, a glass wall that inclines horizontally towards Michigan Avenue, giving you the impression of being suspended in mid air.


The best time to book a flight to Chicago, tour the city, and enjoy the best climate is probably from the end of the summer to the start of autumn, when the weather is most pleasant. The summer months can be very hot, though they are also packed with concerts and cultural events, and there are plenty of goings on in the parks and urban neighbourhoods. The winter, on the other hand, is very cold with plenty of snow, meaning you are usually limited to visiting places indoors.

Check out our offers and book your Alitalia flight to Chicago now!

Weather in Chicago

11 °CFriday23/10/2020
7 °CSaturday24/10/2020
8 °CSunday25/10/2020
5 °CMonday26/10/2020
6 °CTuesday27/10/2020
8 °CWednesday28/10/2020
8 °CThursday29/10/2020
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