Whether it’s your first Chicago holiday or you have visited several times, the famous Windy City skyline never ceases to impress with well over a thousand high-rise buildings, upward of 100 of which stand over 500 feet tall. The tallest of these huge buildings is the 108-story Willis Tower (formerly known as the Sears Tower). All in all, four of America’s tallest buildings stand proudly in the city of Chicago, making it one of the world’s most impressive skylines. Make the most of your holiday to Chicago by checking out these awesome buildings on the Historic Skyscrapers Walking Tour.

Chicago Attractions

Some of the top Chicago attractions include chilling out in Millennium and Grant Parks and taking boat rides on the Chicago River. Navy Pier never fails to make you feel 12 years old again, as you sample 50 acres’ worth of family attractions, amusements and exhibition spaces, including a huge carousel, an indoor ice skating rink, a funhouse maze and the fantastic Chicago Children’s Museum. One of the best ways to see as much of what this great city has to offer as possible is investing in a Chicago CityPass.

Photograph of Diane Williams

Your Plans, Our Expertise

Speak with our Personal Travel Planners and we can build a unique holiday tailored to your exact requirements.

Don’t know the best spot? No problem, we can advise. Got something specific in mind? We can help with that too.

Our Recommended Chicago Offers

Staff Tips

Adrienne Keogh

Chicago's annual summer dance festival is held for 11 weeks each year. Get a free one-hour dance lesson and follow that by indulging in two hours of live music and dancing.

Adrienne KeoghSales and Operations Manager
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