Wander Your Way Around the Windy City: 10 Must-Do Chicago Activities

Chicago’s had record numbers of tourists in the Windy City over the last couple of years. It’s no surprise. The town is vibrant and fun with great food, a plethora of parks and lots of attractions.

Are you visiting Chicago soon?

Read on for 10 must-do Chicago activities.

Millenium Park and the Bean

It wouldn’t be a visit to Chicago if you didn’t make it to Millenium Park. Don’t forget to take your photo at the famous sculpture, Cloud Gate, known as the “Bean” to locals. 

Anish Kapoor created the famous sculpture. Spend some time walking in and around it. The mirrored surface makes for some great reflections of the surrounding city. 

Take your time walking around the park. Stop by the tower fountains. They feature giant faces looking down on the reflecting pool. The faces spurt water from their mouths at intervals. 

While you’re at the Bean, duck across the street to the Chicago Cultural Center and see the Tiffany Dome.

The Willis Tower SkyDeck Chicago

The SkyDeck is at the top of Willis Tower, formerly the Sears Tower. You’ll get an amazing 360-degree view of the city from the observatory.

Are you brave? Take a step onto the 1,353-foot high Ledge. It’s a glass floor extending over 4 feet from the edge of the building. The Ledge’s support system is invisible making the view unparalleled.

Tickets for the Ledge are $24 and include museum exhibits. 

Navy Pier

Some people avoid Navy Pier citing it as a tourist trap. But if you’ve never been to Chicago, you should take some time and explore this historic landmark. Navy Pier is on the shoreline of Lake Michigan. 

It’s over 3,000 feet long and includes parks, shops, restaurants, and attractions.

It first opened in 1916 and was built by Charles Sumner Frost, a well-known architect. It was the Municipal Pier but was renamed in 1927 in honor of WWII navy veterans. 

Navy Pier houses the Chicago Children’s Museum and the Chicago Shakespeare Theater. 

Architecture Cruise

Chicago is host to many famous buildings, and some of the world’s most famous architects are from the Windy City.

Sit back and relax on an architecture cruise. Let an expert point out the unique features and history of Chicago’s buildings. Chicago has over 50 skyscrapers gracing the skyline. 

The Art Institute of Chicago

Don’t miss the Art Institute of Chicago located on Michigan Avenue. You can’t miss the iconic lions flanking the entrance. They were sculpted by Edward Kenny. 

If you’re into the Impressionists, you’ll love the collection of Impressionist paintings. The unforgettable “Sunday on the Island of La Grande Jatte,” by George Seurat is there. 

The Institute is also home to paintings by Georgia O’Keefe, Chagall, and Matisse.

Eat, Eat, Eat

The Windy City is a foodie’s paradise! There are so many unforgettable dishes. Start your day early at one of USA Today’s 10 best coffee and breakfast shops, Cupitol Coffee & Eatery. Read more here. 

Chicago is synonymous with pizza. The locals favor the thin-crust pizza. But you’ve got to try the famous deep dish at least once while you’re there. Try Lou Malnati’s for a deep-dish treat. 

Try an Italian beef sandwich in Little Italy/University Village. Finish your meal with an Italian ice treat. And a visit to Chicago wouldn’t be the same without trying a Chicago dog. Superdawg is a fun retro place serving up great Chicago dogs. 

While you’re hitting up all these fun eateries, don’t forget to log your travels! You won’t want to forget all the great places you’ve visited. 

Wrigley Field

Chicago has some serious sports fans. A visit to Wrigley Field is a must for any sports fan. Even if you’re not a baseball buff, you’ll appreciate this historic baseball park. 

If you don’t have time for a game or you’re there in the off-season, take a tour. For about $25, you’ll get a guided tour lasting almost 90 minutes. The guides are knowledgeable, and you’ll learn lots of fun facts. 

Parking in Chicago is tough and the Wrigley Field area is no exception. Your best bet is public transportation. Take the “L” to the Addison stop. 

The 606

Have you ever been on an urban hiking trail?

Check out the 606. It’s an elevated recreational trail running for almost 3 miles. It’s open from 6 am to 11 pm. If you brought the dog on this trip. the 606 welcomes him too. 

It follows an old abandoned rail line and passes lots of fun bars and restaurants. The rail line was elevated in the late 1800s to eliminate the dangerous ground-level rail crossings.

The 606 trail opened in the early 2000s.  

Shedd Aquarium

Chicago’s Shedd Aquarium is one of the largest in the world. See penguins, sharks, and whales. Touch a stingray. For additional fees, the aquarium offers tours behind the scenes and animal encounters.

Admission runs about $40 for adults, $30 for children. Plan to spend at least half a day there to get the most bang for your buck. If you get a CityPASS or Go Chicago Card, you’ll get one free ticket to the aquarium. 

The Shedd Aquarium is in Grant Park near the Field Museum and Adler Planetarium. 

Grant Park

Grant Park is over 300 acres of green space starting at the eastern edge of the Loop. It runs down close to the South Side. The park is close to Millennium Park. 

Located in Grant Park is the Field Museum and Shedd Aquarium. Don’t miss Buckingham Fountain. Every hour between May and October there’s a 20-minute water show at the fountain.

Buckingham Fountain is one of the world’s largest fountains. Jets shoot water as high as 150 feet into the air. Take note that the fountain closes for the winter. 

The Best Chicago Activities

Now you know what the 10 best Chicago activities are, what are you waiting for? It’s time for your visit to the famous Windy City.

Stand atop the Ledge at SkyDeck Chicago. Eat some of the most delicious food around. Stroll the Navy Pier, and take in a show or two. Visit the Shedd Aquarium and enjoy the city views from Grant Park. 

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