10 Best Things to See and Do in Chicago (USA)

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Chicago aka “The Windy City” is loaded with amazing things to see and do. Situated on the shores of Lake Michigan, the city offers something for everyone. From fantastic restaurants, museums and skyscrapers to expansive parks and great sports venues, Chicago is an amazing city to visit. Here are the 10 best things to do and see in the exciting city of Chicago.

1. Check out the Skydeck at Willis Tower

It’s easy to see why the Skydeck Chicago at the 110-story Willis Tower is one of Chicago’s #1 attractions. Imagine being perched atop North America’s second-tallest building, taking in the awe-inspiring views of the city. On a clear day, you can see all the way to Indiana, Michigan and Wisconsin. The highlight of the Skydeck experience is The Ledge. This glass platform extends out over the streets below as you stand 103 floors above Wrigley Field and Millennium Park.

Visit GetYourGuide to buy a skip the line ticket for your visit. This includes entry to the Skydeck on the 103rd floor, access to The Ledge and various other benefits.

Chicago Skyline

2. Take a Stroll in Millennium Park

A trip to Chicago is not complete without seeing the gorgeous architecture and landscaping of Millennium Park. This 24+ acre spot is a showcase for some pretty cool things.

The Crown Fountain is two towers that face each other on opposite ends of a reflecting pool. These have LED screens that display the faces of Chicago residents. The cool part of the fountain is that the spouts are aligned to make it look like the faces are spitting water on passersby. The 110-ton Cloud Gate is another landmark feature of the park. It’s better known as “the bean” and is forged out of stainless steel, reflecting images of the Chicago skyline.

You can also catch a concert, stroll through the Lurie Garden or just bring a picnic lunch and enjoy the day on the amazing park grounds. You can also be your own guide by downloading the audio tour.

The Bean Chicago at night
Photo by Lance Anderson via Unsplash

3. Catch a Cubs Game at Wrigley Field

Now that the Cubs have finally won the World Series (after a 108-year drought), baseball fans have flocked to catch a “Cubbies” game at legendary Wrigley Field. Wrigley is the second oldest MLB ballpark in the country (after Fenway Park in Boston) and the experience of rooting on the Cubs is unforgettable (Cubs fans are pretty enthusiastic). Fans sitting in the bleachers have the most fun as you’ll be facing towards the batter. If the Cubs aren’t in town, schedule a guided tour of the ballpark. Parking is crazy, so it’s best to take the Chicago L (rapid transit system) to Addison (Red Line).

Baseball at Wrigley Field

4. Visit the Lincoln Park Zoo

The Lincoln Park Zoo is one of Chicago’s most popular attractions. It’s on the north of Chicago in the Lincoln Park neighbourhood. The zoo is home to a wide variety of animals from zebra to hippos to apes. The zoo has done a great job in creating a natural habitat for their furry friends and it will make you feel like you have travelled to the rainforest or are on safari in Africa.

They have great exhibits that highlight some pretty cool animals like African apes, penguins and harbour seals. It’s family and budget-friendly because the zoo does not have an entrance fee (you have to pay for some of the attractions in the zoo). You can’t get there on the Chicago “L”, so try the city bus or a taxi. If you drive, parking is pretty tight and can cost a bit.

5. Explore the Garfield Park Conservatory

If you head Chicago’s west side, you’ll find one of the largest greenhouse conservatories in the US—the Garfield Park Conservatory. The complex has been around for more than 100 years and showcases some of the most stunning botanical displays around. It’s often referred to as “landscape art under glass.” Enjoy the lush fauna of thousands of plant species from all over the world in a tropical indoor setting. The eight indoor display gardens are open all year-round.

During the warmer weather, you can explore 10 acres of outdoor gardens, nature play areas for the kids, a water lily pond, and many more fun activities. Check the website for what programs or events may be going on while you’re in town. Admission is free.

Garfield Park Conservatory
Photo by Jonathan Larson via Unsplash

6. Have an Undersea Adventure at the Shedd Aquarium

For some reason, more people want to visit the Field Museum than this best thing to see in Chicago—the Shedd Aquarium. It’s their loss because the Shedd is one of the best aquaria in the country. They opened their doors in 1930 and for a long time, was the largest aquarium in the US. Shedd’s Waters of the World gallery features exhibits on oceans, rivers, islands and lakes all in the heart of Chicago. The stars of the show are the beluga whales, rockhopper penguins and alligators, but don’t forget to check out the giant Pacific octopus and starfish and all the other sea creatures that called the aquarium home.

Photo by Silas Hao on Unsplash

7. Feel Like a Kid Again at the Navy Pier

Jutting out into the Great Lake of Michigan is the one and only Navy Pier, a family-friendly getaway spot. The 196-foot-tall Ferris wheel dominates the Chicago skyline and is a great way to get a bird’s eye view of the Windy City. Once you have experienced all the rides, you can explore the other fun activities like the 18-hole miniature golf course and the Chicago Children’s Museum.

The Navy Pier is not just for kids, grown-ups can catch a play at the Chicago Shakespeare Theater, browse the many shops, take a dinner cruise on the lake or grab a brew at the Miller Lite Beer Garden. End the night with a bang! During the summer there are concerts and a nighttime firework show. Admission to the park is free, but you’ll have to pay to enjoy the rides. The best way to get to the park is aboard the free Navy Pier trolley.

Chicago Navy Pier

8. See Impressive Collections at the Art Institute of Chicago

The Art Institute of Chicago is home to one of the most impressive displays of art in the country. Its collection of works come from all over the world. The Art Institute’s most popular exhibits feature the impressionist collection that includes works from van Gogh, Monet and Renoir. The museum also has a collection of pretty cool artefacts that showcases interior design and furniture from Europe and America.

There are always fantastic travelling exhibits that stop in Chicago to show off a variety of artists and genres. The museum is right next to Millennium Park and is easy to get to via the Jackson or Monroe L stations. Admission is $25 for adults, but if you have a CityPASS or a Go Chicago Card, it’s included in your pass (along with entry to a bunch of other popular Chicago attractions).

The Art Institute of Chicago


9. Shop the Magnificent Mile

If you want to experience endless shopping, amazing food and magnificent architecture and the best entertainment in town, then you have to head to North Michigan Avenue and check out the “Magnificent Mile”. It is one of the world’s great avenues and what makes Chicago a truly international vacation spot. This 13-block stretch in the heart of the city runs from the shores of the Chicago River to the Landmark Drake Hotel, one-mile to the north. With hundreds of stores and restaurants and scores of hotels and entertainment venues, this slice of Chicago has something for every taste, passion and budget.

Downtown Chicago Magnificent Mile

10. Live History at the Field Museum

The Field Museum is one of Chicago’s most visited attractions and sits on a half an acre of land in the city’s popular Grant Park. The Field Museum is filled with exhibits that will amuse and intrigue visitors of all ages. The Ancient Egypt exhibit is probably the biggest draw (not just because it was the home base for Indiana Jones). Check out the three-story Egyptian tomb and the interactive story of life on the Nile. Another must-see exhibit is all about the dinosaur. SUE is the museum’s T. Rex. She’s 40 foot long and her sharp teeth are pretty scary. There are so many other things to learn but you’ll need to set aside the whole day to discover them all. Admission to the Field Museum is also included in the CityPASS and Go Chicago Card.

T Rex at the Field Museum
Photo by Chris Nguyen via Unsplash

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James Stewart

Written by

James Stewart

Jim is a travel writer and retired lecturer of African Studies. He is a self-described life-long trekker and his career as a U.S. Air Force officer gave him the chance to experience amazing and exotic destinations in Europe, Asia and Africa. He is at home with a good Wilbur Smith book or anywhere there is a story to tell... [Read full bio]

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