What to do in Chicago?

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Claire

Travel Expert

Chicago is a city bursting with culture, history, and unforgettable experiences, making it a must-visit destination for travelers of all kinds. From iconic landmarks like Millennium Park and the Willis Tower to vibrant neighborhoods and world-class museums, there’s no shortage of things to do in Chicago. Whether you’re a foodie, an art enthusiast, or an architecture lover, this guide to the best things to do in Chicago will help you uncover the highlights and hidden gems that make the Windy City truly one of a kind.

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1. Millennium Park and Cloud Gate

Millennium Park and Cloud Gate what to do in chicago

Snap the Perfect Selfie at Chicago’s Iconic Landmark

When searching for what to do in Chicago, visiting Millennium Park and its iconic Cloud Gate (affectionately called The Bean) is non-negotiable. This sprawling park in the heart of downtown Chicago is the ultimate blend of art, architecture, and nature. Stroll through the beautifully landscaped grounds, take in the contemporary sculptures, and enjoy free events like concerts or film screenings in the summer months. The main attraction, The Bean, is a reflective sculpture that creates mesmerizing photo opportunities, mirroring the city skyline and vibrant activity around it. Millennium Park is part of the larger Grant Park, which is often buzzing with locals and visitors alike. Whether you’re a casual explorer, art lover, or simply want a cost-free yet unforgettable experience, this spot has something for everyone. From winter ice skating to summer art festivals, it’s a year-round destination that captures Chicago’s urban energy. Perfect for travelers on a budget or families exploring the city together, it’s the place to start your Chicago adventure.

Average Price Per Person: Free

2. Art Institute of Chicago

Art Institute of Chicago what to do in chicago

World-Class Art in the Heart of the Windy City

Wondering what to do in Chicago for art enthusiasts? The Art Institute of Chicago is a cultural jewel you can’t miss. This prestigious museum houses an impressive collection of over 300,000 works of art, spanning thousands of years and cultures. Renowned for its masterpieces like Van Gogh’s The Bedroom and Georges Seurat’s A Sunday Afternoon, the museum offers an unforgettable experience for both casual visitors and art aficionados. Wander through galleries showcasing everything from ancient artifacts to modern contemporary installations. The Thorne Miniature Rooms and the iconic Impressionist Wing are visitor favorites, offering something uniquely Chicago while also celebrating global creativity. The Art Institute’s prime location near Millennium Park makes it an easy addition to your itinerary. Whether you’re exploring solo or with loved ones, you’ll find inspiration in every corner. Don’t forget to grab a coffee at their charming café and browse the gift shop for unique art-inspired keepsakes.

Average Price Per Person: $32; discounts for students, seniors, and children

3. Navy Pier

Navy Pier what to do in chicago

Entertainment, Dining, and Lakefront Views for Everyone

If you’re researching what to do in Chicago, Navy Pier is where excitement and leisure meet. Located along the stunning shores of Lake Michigan, Navy Pier offers a variety of experiences for all ages. This historic landmark boasts a mix of attractions, including its iconic Centennial Wheel, where panoramic city views await. Families can enjoy the Chicago Children’s Museum or hop on a lake cruise, while couples will love the romantic dining spots overlooking the water. During the summer months, Navy Pier hosts vibrant fireworks displays, outdoor concerts, and art exhibitions. Take a walk along the pier to enjoy public art, live street performers, and bustling energy all around. With dining options ranging from deep-dish pizza to waterfront cocktails, it’s easy to spend an entire afternoon here. Whether you’re on a budget or looking to splurge on experiences, Navy Pier guarantees lasting memories and incredible views of Chicago’s skyline.

Average Price Per Person: Free entry (attractions like the Ferris wheel cost around $15–$20)

4. Chicago Architecture River Cruise

Chicago Architecture River Cruise what to do in chicago

See Chicago’s Skyline from the Water

If you’re wondering what to do in Chicago to truly appreciate its architectural wonders, the Chicago Architecture River Cruise is a must-do. This guided boat tour takes you through the heart of the city via the Chicago River, providing unbeatable views of the skyline and fascinating insights into Chicago’s iconic buildings. Whether you’re an architecture buff or a casual tourist, the detailed commentary will open your eyes to how Chicago became the birthplace of the skyscraper. You’ll pass famous landmarks like the Willis Tower, Wrigley Building, and the John Hancock Center while learning about the architects and history behind them. Most tours last 75–90 minutes, making it a great way to see the city from a different perspective without taking up your entire day. Sit back, relax, and snap stunning photos as the boat cruises beneath Chicago’s picturesque bridges. Evening tours often provide a dazzling look at the skyline lit up at night—an unforgettable sight for visitors.

Average Price Per Person: $45–$55 (varies by tour operator)

5. Lincoln Park Zoo

Lincoln Park Zoo what to do in chicago

A Wildlife Escape in the Middle of the City

Looking for family-friendly ideas for what to do in Chicago? Head to Lincoln Park Zoo, one of the oldest zoos in the United States and completely free to the public. Located in the beautiful Lincoln Park neighborhood, this urban zoo is home to a wide variety of animals, from majestic lions to playful penguins and gorillas. Wander through well-designed exhibits like the Regenstein Center for African Apes or explore the lush gardens that make this zoo feel like a peaceful retreat from city life. It’s the perfect stop for families, nature enthusiasts, or anyone looking to spend a leisurely afternoon surrounded by wildlife. Seasonal events like ZooLights in winter or outdoor concerts during summer add even more value to this iconic attraction. Because entry is free, it’s also a great budget-friendly option that doesn’t skimp on excitement. Pair your zoo visit with a stroll around the nearby Nature Boardwalk for an added dose of Chicago’s natural beauty.

Average Price Per Person: Free

6. Willis Tower Skydeck

Willis Tower Skydeck what to do in chicago

Stand on the Ledge and See Chicago from New Heights

When deciding what to do in Chicago, a visit to the Willis Tower Skydeck should be on your list for an unforgettable skyline experience. As one of the tallest buildings in the Western Hemisphere, Willis Tower offers unparalleled 360-degree views of the city and beyond. Located on the 103rd floor, the Skydeck features The Ledge—a series of glass-floored balconies that extend out from the building. Standing on The Ledge is both exhilarating and Instagram-worthy, providing you with heart-stopping views of the city below. On clear days, you can see up to four states stretching into the horizon. The Skydeck also offers educational displays highlighting Chicago’s history, architecture, and neighborhoods, making it both entertaining and informative. Whether you visit during the day or at sunset, the views are breathtaking. It’s the perfect activity for solo travelers, couples, or families who want to experience Chicago from a completely new perspective.

Average Price Per Person: $30–$45

7. Museum of Science and Industry

Museum of Science and Industry ​what to do in chicago

An Interactive Journey Through Science and Innovation

Curious about what to do in Chicago that’s both educational and entertaining? The Museum of Science and Industry is the answer. Known for its hands-on exhibits and immersive displays, this massive museum offers something for everyone. Explore a real U-505 submarine, watch baby chicks hatch, or walk through a simulated tornado in the Science Storms exhibit. For space enthusiasts, the replica Apollo 8 spacecraft is a must-see, while the Model Railroad showcase will captivate train lovers of all ages. One of the museum’s highlights is The Coal Mine, a popular exhibit that takes you on a simulated journey deep underground. The museum is designed to inspire curiosity, making it an ideal stop for families, students, and anyone with a love of science. You could easily spend an entire day here, so plan accordingly! With its vast range of exhibits, this museum is both a top-tier attraction and a memorable experience in Chicago.

Average Price Per Person: $25–$33 (additional fees for special exhibits)

8. Wrigley Field

Wrigley Field what to do in chicago

Experience Baseball History at Chicago’s Legendary Stadium

If you’re a sports fan looking for what to do in Chicago, a visit to Wrigley Field is a must. Built in 1914, Wrigley Field is home to the Chicago Cubs and remains one of the most iconic and historic baseball stadiums in the United States. Even if you’re not attending a game, guided tours of Wrigley Field offer a behind-the-scenes look at this legendary ballpark. Walk through the dugout, step onto the field, and soak in the charm of its ivy-covered walls and classic scoreboard. A Cubs game here is an unforgettable experience, with fans creating an electric atmosphere that will leave you cheering for more. The surrounding neighborhood, Wrigleyville, is also packed with bars, restaurants, and shops, making it a great spot to spend the day. Whether you’re a baseball fan or just curious about Chicago’s sports culture, Wrigley Field offers a perfect mix of history, excitement, and nostalgia.

Average Price Per Person: $25–$100+ (varies by game or tour)

9. Chicago Riverwalk

Chicago Riverwalk what to do in chicago

Stroll, Dine, and Relax Along Chicago’s Scenic Riverfront

For anyone wondering what to do in Chicago, the Chicago Riverwalk is an essential stop. This vibrant urban space stretches along the Chicago River, offering a perfect mix of leisure, dining, and entertainment. Whether you’re up for a scenic walk, grabbing a coffee, or sitting back to enjoy the riverside atmosphere, there’s something for everyone here. Stop by riverside restaurants and bars for a cocktail with a view, or grab a kayak rental to explore the river at your own pace. Art lovers will enjoy spotting public art installations scattered along the path, while architecture buffs can marvel at the buildings towering above. The Riverwalk comes alive in the evening, with twinkling lights and reflections from the water creating a romantic atmosphere. Families, couples, and solo travelers alike will love this free and beautiful space for unwinding. It’s a great place to watch boats pass by, snap stunning photos, and enjoy Chicago’s energy up close.

Average Price Per Person: Free 

10. Shedd Aquarium

Shedd Aquarium what to do in chicago

Dive into a World of Marine Life at Chicago’s Top Aquarium

Looking for family-friendly ideas for what to do in Chicago? Head to the Shedd Aquarium, a world-class destination showcasing aquatic life from around the globe. Located along the scenic Museum Campus, Shedd Aquarium is home to over 32,000 fascinating creatures, from vibrant tropical fish to playful sea otters and majestic beluga whales. Explore immersive exhibits like the Caribbean Reef, where you’ll see rays and sharks up close, or head to the Oceanarium to witness incredible dolphin shows and underwater viewing experiences. Interactive touch tanks and educational programs make it a hit with kids and adults alike. The aquarium’s central location means you can easily pair your visit with other nearby attractions like the Field Museum or Adler Planetarium. Whether you’re a marine enthusiast or simply love discovering the natural world, the Shedd Aquarium offers a captivating adventure you won’t forget.

Average Price Per Person: $39.95–$49.95

11. The Second City

The Second City what to do in chicago

Laugh Out Loud at Chicago’s Legendary Comedy Club

If you’re searching for what to do in Chicago at night, don’t miss a show at The Second City. As one of the most iconic comedy theaters in the world, The Second City has launched the careers of comedic legends like Tina Fey, Steve Carell, and Bill Murray. Located in the lively Old Town neighborhood, this venue hosts improv and sketch comedy shows that are guaranteed to have you laughing out loud. Each performance is unique, with comedians riffing on current events, pop culture, and audience interactions. Grab a drink, settle into the intimate theater, and enjoy a night of quick-witted humor. The Second City offers a variety of shows to suit all tastes, from classic sketch comedy to cutting-edge improv, making it a must-visit spot for fans of live entertainment. Whether you’re on a date night, out with friends, or just love comedy, this experience is an unforgettable slice of Chicago’s culture.

Average Price Per Person: $30–$60

12. Chicago Cultural Center

Chicago Cultural Center what to do in chicago

Art, Architecture, and Free Events in a Stunning Setting

For a budget-friendly answer to what to do in Chicago, visit the Chicago Cultural Center. Known for its stunning architecture and free exhibitions, this historic building is a cultural hub in the heart of the city. The center’s highlights include the breathtaking Tiffany glass dome—the largest of its kind in the world—and beautifully designed mosaics and marble interiors. Visitors can explore a rotating selection of art exhibitions, concerts, and cultural events, all free of charge. It’s the perfect stop for those who appreciate art, history, and architecture without breaking the bank. The Cultural Center also frequently hosts lectures, workshops, and film screenings, making it a dynamic destination for travelers looking to experience Chicago’s creative pulse. Whether you’re wandering through the galleries or just marveling at the stunning interiors, this iconic spot offers a peaceful escape in the heart of the bustling city.

Average Price Per Person: Free

13. Garfield Park Conservatory

Garfield Park Conservatory what to do in chicago

Discover a Tropical Oasis in Chicago’s West Side

If you’re exploring what to do in Chicago and want a break from the city’s urban energy, the Garfield Park Conservatory is a hidden gem. Often called “landscape art under glass,” this lush conservatory is one of the largest in the United States and offers an enchanting escape into nature. Inside, you’ll find thousands of plant species across various themed rooms, from tropical palms and ferns to desert cacti and blooming flowers. Visitors can walk through the Palm House, relax in the Fern Room, or marvel at the seasonal displays, which are carefully curated throughout the year. Admission is free, making it a perfect budget-friendly outing for nature lovers, photographers, and families. Don’t miss the outdoor gardens during warmer months, where pathways wind through colorful landscapes and ponds. Whether you visit in winter or summer, the Garfield Park Conservatory provides a refreshing dose of greenery and tranquility in the heart of the city.

Average Price Per Person: Free (donations encouraged)

14. Magnificent Mile

Magnificent Mile what to do in chicago

Shop, Dine, and Explore Chicago’s Famous Boulevard

If shopping and city sights are on your list of what to do in Chicago, the Magnificent Mile is your go-to destination. This bustling stretch of Michigan Avenue is home to high-end boutiques, flagship stores, and world-class dining. Whether you’re window shopping or indulging in a spree, you’ll find everything from luxury brands to unique local shops. Beyond shopping, the Magnificent Mile is surrounded by iconic attractions like the historic Water Tower, the John Hancock Center, and beautiful public art installations. Stop for a meal at one of the many restaurants or cafes, where you can enjoy anything from Chicago-style deep-dish pizza to upscale cuisine. During the holiday season, the area transforms into a dazzling winter wonderland, with twinkling lights and festive displays drawing visitors from all over. The Magnificent Mile is more than just a shopping destination—it’s a vibrant hub where fashion, food, and culture collide.

Average Price Per Person: Free

15. Chicago Blues Clubs

Chicago Blues Clubs what to do in chicago

Experience the Soul of the City with Live Blues Music

For music lovers seeking what to do in Chicago, visiting a Chicago blues club is a must. The city is the birthplace of electric blues, and its vibrant music scene continues to thrive in venues like Buddy Guy’s Legends, Kingston Mines, and Rosa’s Lounge. These intimate clubs showcase talented local musicians and traveling artists who keep Chicago’s rich blues tradition alive. Spend an evening soaking in soulful guitar riffs, heartfelt vocals, and the warm, welcoming vibe that blues clubs are known for. Many venues offer food and drinks, so you can enjoy classic Chicago eats while listening to live music. Whether you’re a blues aficionado or a casual listener, these clubs provide an unforgettable night out that’s uniquely Chicago. The energy, passion, and authenticity of a live blues performance will leave you with a deeper appreciation for the city’s cultural heritage.

Average Price Per Person: $15–$30 cover charge

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