10 Best Things to Do in Chicago for Your First Visit

Planning a trip to Chicago? Before diving into the city’s top attractions, here are a few Chicago facts to set the scene. Known as “Chi-Town,” Chicago sits in northeastern Illinois along the southwestern shore of Lake Michigan. It is famously the birthplace of skyscrapers and is renowned for its museums, architecture, deep-dish pizza, vibrant neighborhoods, lakefront parks, music scene, and lively nightlife. Every year, it attracts visitors from all over the world.

Whether it’s taking a selfie in front of The Bean, strolling along the Chicago Riverwalk, catching a Cubs game at Wrigley Field, or experiencing an architectural boat tour, Chicago has something for everyone. Below is a list of the best things to do in Chicago to make your first visit unforgettable.

Millennium Park is one of Chicago’s most famous attractions and a perfect starting point. It is home to Cloud Gate, the mirrored sculpture popularly known as The Bean, which reflects the city skyline and makes for incredible photos.

The park also features:

• Lurie Garden, perfect for peaceful walks
• Jay Pritzker Pavilion, for free concerts and events
• Crown Fountain, an interactive digital artwork

In winter, ice skating is available at the park’s McCormick Tribune Ice Rink. Millennium Park also hosts seasonal events, green spaces, and is conveniently connected to downtown landmarks, including the Art Institute of Chicago.

The Chicago Riverwalk is a 1.25-mile path along the Chicago River, offering scenic waterfront views, public art, and food and drink options. Stroll, relax, or sip a drink at City Winery while watching boats pass by.

The Riverwalk is divided into several areas:

• The Confluence, ideal for photos
• The Arcade, lined with cafes and artwork
• The Esplanade, featuring eateries and bars

Visitors can also explore the Vietnam Veterans Memorial Plaza, Bridge House Museum, floating gardens, or enjoy kayaking and architectural boat tours along the river.

A guided architectural boat tour on the Chicago River is one of the city’s signature experiences. These tours highlight landmarks like Marina City, Wrigley Building, John Hancock Center, and Tribune Tower. Knowledgeable guides share insights about Chicago’s reconstruction after the Great Fire of 1871 and its architectural innovations.

Tours are available throughout the day, but early evening cruises are especially popular for sunset views over the skyline. First-time visitors will gain a deeper appreciation for Chicago’s architecture while enjoying the scenic river views.

For breathtaking city views, visit one of Chicago’s two famous observation decks:

• Willis Tower Skydeck: Located on the 103rd floor, featuring The Ledge, a glass balcony extending over the city streets below.
• 360 Chicago at John Hancock Center: Offers TILT, an experience that tilts visitors outward for a thrilling view of Michigan Avenue.

Both decks include interactive exhibits detailing Chicago’s history and architecture. Pre-booking tickets is recommended to skip the lines.

Chicago is a haven for food lovers, and a food tour is an excellent way to explore its culinary scene. Try local specialties such as:

• Deep-dish pizza– buttery crust, rich tomato sauce, and melted mozzarella
• Chicago-style hot dogs– topped with mustard, onions, relish, tomatoes, pickles, and sport peppers
• Italian beef sandwiches– thinly sliced beef with giardiniera

Popular pizza spots include Giordano’s (cheese-heavy pizzas) and Lou Malnati’s (generous toppings). A food tour lets you sample several iconic dishes in a short time while learning about Chicago’s unique culinary traditions.

The Museum Campus, along Lake Michigan, is home to three world-class attractions:

• Field Museum: Features natural history exhibits, including Sue, the largest T. rex skeleton in the world.
• Shedd Aquarium: Houses over 1,500 species, including penguins, sea otters, and tropical fish, along with interactive exhibits and conservation programs.
• Adler Planetarium: Offers historical spacecraft like Gemini 12, space exhibits, and scenic skyline views from its terrace.

Visitors can easily spend half a day exploring the museums while enjoying the lakefront scenery.

Wrigley Field, built in 1914, is one of the oldest and most recognizable baseball stadiums in the U.S. It is home to the Chicago Cubs and is famous for its hand-operated scoreboard and ivy-covered outfield walls.

On game days, the stadium is buzzing with excitement from fans cheering every pitch. Enjoy traditional ballpark fare like hot dogs and Garrett Popcorn while soaking in the atmosphere. The area surrounding the stadium is also lively, with bars, restaurants, and pre- and post-game activities.

Lincoln Park is a beautiful neighborhood centered around a large lakefront park. Highlights include:

• Lincoln Park Zoo: Free admission, with lions, gorillas, penguins, and more
• Lincoln Park Conservatory: Tropical plants and tranquil indoor paths
• Honeycomb Pavilion: Scenic views of the city skyline

The area is also home to museums such as the Chicago History Museum and Peggy Notebaert Nature Museum, along with notable restaurants like Alinea and Boka.

North Avenue Beach, on Lake Michigan, is a must-visit in summer. It features sandy shores, skyline views, and a beach house that resembles an ocean liner.

Activities include:

• Swimming and sunbathing
• Volleyball, biking, kayaking, and paddleboarding

The Castaways Bar & Grill, located in the beach house, offers food, drinks, and rooftop views—a perfect place to relax by the water.

The Magnificent Mile, a one-mile stretch of Michigan Avenue from Oak Street to the Chicago River, is Chicago’s premier shopping destination. Highlights include:

• Water Tower Place: Shops like Sephora, Macy’s, and American Girl Place
• 900 North Michigan Shops: Bloomingdale’s, designer boutiques, and luxury stores
• Flagship stores like Appleand Nike

The area also features historical landmarks, tall buildings, and a vibrant atmosphere, making it a must-visit for shopping enthusiasts.

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