A Windy City Bucket List: 8 Essential Things to Do in Chicago

What do you imagine when you think about visiting Chicago?

Is it the delicious food scene and mouthwatering deep-dish pizza? Is it the pretty parks and countless museums on offer? Or what about the stunning architecture housing some of the best nightlife nationwide?

Of the 60 million tourists who visit the windy city, everyone will have a different image in their heads. That’s because there are endless things to do in Chicago and areas to explore.

A Chicago trip is a once-in-a-lifetime opportunity. Yet, if you don’t research before you arrive, you could miss out on some top attractions and landmarks.

If you want to discover eight things to put on your Chicago travel itinerary, read our guide below!

1. Venture Through Millennium Park

Millennium Park is a 24.5-acre public park in the heart of downtown Chicago. It is a perfect place to start your journey and immerse yourself in the city’s vibrant atmosphere. 

The park is famous for its iconic Cloud Gate sculpture, known by locals as “The Bean.” 

Take a stroll through the park’s beautiful landscaped gardens. And if you are lucky, you can catch a free concert or movie screening at the Jay Pritzker Pavilion in the summer. 

Don’t forget to visit the Crown Fountain, where you can cool off in the interactive water features.

2. Visit the Art Institute of Chicago

This establishment is one of the largest and oldest art museums in the United States. It houses a collection that spans over a thousand years and includes works from around the globe. 

You can marvel at pieces like Grant Wood’s “American Gothic” and Vincent van Gogh’s “The Bedroom.” But the museum also features an impressive collection of contemporary and modern art. 

It’s easy to get lost in displays. So be sure to give yourself enough time to explore the museum’s vast halls and galleries.

3. Take an Architectural Boat Tour

If you have ever seen a photo of Chicago, you’ll have noticed its impressive architecture. One of the best ways to experience it is by taking an architectural boat tour along the Chicago River. 

These guided tours provide a unique view of the city’s skyline. They also offer a fascinating insight into its architectural history. 

Admire towering skyscrapers, including the iconic Willis Tower and the Tribune Tower. Or learn about famous architects like Frank Lloyd Wright and Mies van der Rohe. Both are people who left their mark on the city’s skyline. 

The boat tours are informative and entertaining. Thus it makes them an excellent choice for architecture enthusiasts and casual visitors.

4. Catch a Game at Wrigley Field

If you’re a sports fan, you shouldn’t miss the chance to experience a baseball game at the home of the Chicago Cubs. 

Known for its charm and lively atmosphere, Wrigley Field is one of the oldest ballparks. The stadium has a capacity of 41,118, but you should still try to book your tickets in advance.

Even if you’re not a baseball fan, attending a game here is an essential Chicago experience. You will enjoy the electric energy, savor classic food, and view the ivy-covered walls.

5. Explore Navy Pier

Navy Pier is a bustling entertainment destination on the shores of Lake Michigan. It offers many attractions, like amusement park rides, a Ferris wheel, and an IMAX cinema.

You can stroll along the pier while enjoying the glimmering lake and try tasty meals at one of the eateries.

The pier hosts fireworks displays, outdoor concerts, and other local events in summer. So, if you’re visiting Chicago as a family, put Navy Pier at the top of your travel itinerary!

6. Wander Through Chicago’s Neighborhoods

Chicago has diverse communities, each with a unique character and charm. Since the city sprawls 234 square miles, it’s no surprise that no two neighborhoods are alike.

Take the time to explore neighborhoods like Wicker Park. People know it for its vibrant art scene, trendy boutiques, Lincoln Park Zoo, and dining options. 

Next, head to Chinatown. You get to experience a different cultural atmosphere and enjoy authentic Chinese cuisine.

Make sure you also visit the historic neighborhoods of Wrigleyville and Boystown. These areas are known for their energetic nightlife and offer an array of bars, clubs, and live music.

7. Sample Chicago’s Food Scene

No visit to Chicago is complete without trying its famous culinary specialties. The city is renowned for its deep-dish pizza. So grab a slice at iconic pizzerias like Lou Malnati’s or Giordano’s. 

Don’t miss the chance to sample a classic Chicago-style hot dog. These mouthwatering delicacies are topped with mustard, relish, onions, tomatoes, pickles, and peppers. Also, don’t forget to try some Chicago-style popcorn, a delightful mix of a caramel and cheese snack.

For a more upscale dining experience, explore the city’s diverse restaurant scene. They range from a Michelin-starred establishment to a romantic dinner cruise.

8. Experience the Museum Campus

Last but not least, your Chicago trip should include The Museum Campus. It is a park located on the shores of Lake Michigan, featuring three world-class museums. 

Start at the Field Museum, which showcases a collection of natural history artifacts. Arguably the most popular display is the famous T. rex skeleton named Sue. 

Next, head to the Shedd Aquarium, where you will see the aquatic ecosystem and witness marine life. End your journey at the Adler Planetarium. You can dive into universal wonders through interactive exhibits and planetarium shows. 

The Museum Campus also offers stunning views of the Chicago skyline. This makes it the ideal spot for a leisurely walk, picnic, or family photoshoot.

Jump Into the Best Things to Do in Chicago!

Before the turn of the century, Chicago exploded onto the tourist map. It’s easy to see why, with its vast quantity of museums and galleries and quality bars and restaurants.

Today people still flock here to appreciate this fascinating city. It doesn’t matter if you come to relax, sightsee, or party. There are countless things to do in Chicago to keep you entertained!

After reading our guide, you know how to make the most of your time. But if you want to uncover more travel planning tips, tricks, and more for your journey, keep reading our blog!


Hi, I am Friedman the admin of this blog. I am very passionate in blogging and I love to share informative, authentic contents on entertainment, health, travel, technology, fashion, latest trends, business, digital marketing etc on my blog

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