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10 Things To Do in Chicago

If these aren't on your Windy City bucket list, they need to be.

By Lynsey Elve on December 3, 2021

Courtesy of Puparrazi Photography

Ah, sweet home Chicago. So much to do and see in the nation’s third largest city, but with so many nooks and crannies to explore it’s hard to know which activities and sights to prioritize. That’s where we come in. Below are the 10 bucket list things you have to do in the Windy City. While some may be considered “touristy” and others hidden gems, all will produce memorable moments!

1. Walk the shores of Lake Michigan

Lake Michigan is hands down one of the best things about living and visiting Chicago. The lake shore boasts 26 miles of beautiful public beaches, from North Avenue Beach to Montrose Beach, with 18.5 miles of trails and green space for hiking, biking, volleyball playgrounds, baseball diamonds, tennis courts and soccer fields. One wonderful new addition to the lake shore is a beautiful green space near Fullerton Avenue. Take a seat on a bench and watch the sunset behind the skyline.

2. Visit Millennium Park

Located in the heart of the city, Millennium Park is a must-experience in Chicago. The park itself is a state-of-the-art collection of architecture, landscape design and art including hundreds of free concerts, tours and family activities (there is something free to do every day!). The crown jewel of Millennium Park is the famous “Bean,” a single stainless-steel object 66 feet long, 33 feet high and 42 feet wide designed to reflect the cityscape (pictured below). It was designed by Anish Kapoor and has become a cherished treasure in the city.

Millenium Park Chicago IL
Chicago / Jeff Adkins

3. Take in the many museums

From science and industry to art and history of all kinds, Chicago offers so many museums for local city dwellers and visitors to explore all year round. Some favorites include The Field Museum with the famed “Sue,” the largest and most complete Tyrannosaurus rex skeleton ever; the Museum of Science and Industry with a Boeing 727 sitting inside it; and the Shedd Aquarium, with more than 8,000 aquatic animals. If you’re looking for cultural history, visit the Chicago Cultural Center with its remarkable stained glass domes and ongoing mix of free music, dance, films, lectures and art exhibitions.

4. Enjoy Restaurant Row

The land of food and drink resides in Chicago’s West Loop neighborhood on Randolph Street. The area, affectionately called “Restaurant Row” is lined with some of the best restaurants, bars and eateries in the city, state and nation. Anchored by Stephanie Izard’s renowned Girl and the Goat, this area includes culinary and cocktail standouts including Au Cheval, Green Street Meats and SoHo House Chicago. Izard’s newest creation is Duck Duck Goat, an Asian-inspired food lovers dream.

5. Have a cocktail at the top of the John Hancock building

The view from the top of the John Hancock building is amazing. It can be a bit of a tourist trap, so instead of visiting the official observatory deck, head to the 95th or 96th floor for a cocktail, a meal, or both at the Signature Room and enjoy sweeping views of the city and lake shore without putting up with throngs of tourists. You pay a bit more for the view, but it’s a great experience and they make a superb Bloody Mary.

6. Visit Lincoln Park Zoo

One of the nation’s oldest zoos, The Lincoln Park Zoo houses 1200 animals representing 230 species and guess what? It’s open 365 days a year and it’s free to the public. It sits just off the lake shore in the Lincoln Park neighborhood, and is a popular place to be year-round. In the winter months the establishment hosts “ZooLights” a holiday light show of amazing proportions (nearly 2 million lights!) that can put the biggest Scrooge in the holiday spirit.

7. Indulge at Annette’s Italian Ice

If you want to experience a lovely little neighborhood off the beaten path and dig in to some amazing Italian ice and ice cream, you should visit Annette’s Italian Ice, nestled in the quaint Armitage shopping district. The flavors are endless, the staff is wonderful and it’s not too busy. Try the “cookie jar” or “Tennessee toffee” ice cream with a hard chocolate shell. You’re thank us later.

8. Take an architecture tour

If it’s nice in Chicago, you definitely want to be on a boat. There are so many different boat tours offered in Chicago, one of the city favorites is the Wendella Architecture Tour including 75 minutes of cruising down the river and looking at and learning about the Chicago skyline. If architecture and history aren’t your thing, you can also experience a variety of other river cruises including sunset wine and cheese rides or Barbecue and Beer cruises to name a few.

9. Visit the Willis Tower Skydeck

The Willis Tower (formerly Sears Tower) is the largest building in the Western Hemisphere at 1,353 feet. The Skydeck sits atop this behemoth building and offers amazing views of Chicago and three other states. The most exciting and terrifying experience of the Skydeck is “The Ledge,” a glass balcony extending four feet off the 103rd floor of the Tower.

10. Take a selfie on one of Chicago’s moveable bridges

The scenery from Chicago’s 18 different moveable bridges is an Instagramers dream! If you’re in the “Loop” take a few minutes to check out the different bridges and take a selfie from any one of the bridges with your photo pointed towards the east. The water, boats, other bridges and skyscrapers in the background makes for one memorable photo.

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