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 Sarah McCormick

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
Fiona Kelly

Chicago- Head to the underwater viewing area to catch a glimpse of swimming sea lions or take a guided tour of the hundreds of species on view at the Lincoln Park Zoo. Admission to the zoo is free seven days a week.

Fiona KellyPersonal Travel Planner
Claire Somers

Chicago - You can't go wrong with the Wiener Circle or Byron's, both by Wrigley Field, for a genuine Chicago dog & fries experience. For deep dish pizza, Uno/Due are owned by the same place so you'll get an equally wonderful meal at either. Be prepared to wait though, the lines can be 2 hours long in summer. Giordano's is an acceptable alternative.

Claire SomersPersonal Travel Planner
Denise Walsh

Chicago - See a free water display every hour at the Buckingham Fountain from mid-April to mid-October. The best time to go is between dusk and 10 p.m. when the fountain's 134 spouting jets are accompanied by a music and light display.

Denise WalshPersonal Travel Planner
Adrienne Keogh

Chicago - Definitely check out Wrigley Field, home of the Chicago Cubs baseball team. Catch a game and enjoy the experience of attending an American baseball game or enjoy a stadium tour. With over 100 years of history there's lots to see and learn!

Adrienne KeoghSales and Operations Manager
Go back