Chicago, the Windy City, is a vibrant metropolis brimming with culture, history, and unforgettable experiences. From iconic architecture and world-class museums to deep-dish pizza and stunning lakefront views, there’s something for everyone.
Whether you're a first-time visitor or a lifelong local, this guide highlights the 20 best things to do in Chicago that capture the heart and soul of the city.
1. See The Bean (Cloud Gate) at Millennium Park
Cloud Gate, affectionately known as "The Bean," is one of Chicago’s most iconic landmarks. Its mirrored surface reflects the city skyline and the surrounding park, offering visitors a unique and interactive visual experience. Located in Millennium Park, it's a must-see spot for photo opportunities and people-watching.
The sculpture, designed by Anish Kapoor, captures the spirit of modern Chicago through its bold, artistic design. It draws millions of visitors annually, making it a central part of any Chicago itinerary. Both locals and tourists alike are captivated by its beauty and creative charm.
2. Visit Chicago's front yard: Grant Park
Grant Park, often called “Chicago’s front yard,” is a sprawling urban oasis in the heart of the city. It offers scenic green space, walking paths, and stunning views of Lake Michigan. Home to Buckingham Fountain, it's a perfect place to relax or take in the skyline.
The park also hosts major cultural events like Lollapalooza and Taste of Chicago. With nearby attractions such as the Art Institute and Museum Campus, it serves as a hub of activity. Its central location makes it an essential stop for anyone exploring downtown Chicago.
3. Art Institute of Chicago
The Art Institute of Chicago is one of the oldest and most renowned art museums in the world. It houses an extraordinary collection, including masterpieces like A Sunday on La Grande Jatte and American Gothic. Art lovers are drawn to its vast galleries, which span centuries and continents.
Beyond its iconic artworks, the museum offers engaging exhibitions, educational programs, and a stunning modern wing. Located in Grant Park, it's easily accessible and surrounded by other cultural landmarks. Its rich offerings make it a cornerstone of Chicago’s vibrant arts scene
4. Shop till you drop on The Magnificent Mile
The Magnificent Mile is Chicago’s premier shopping destination, stretching along North Michigan Avenue. It features everything from luxury boutiques and flagship stores to popular retailers. Shoppers can enjoy a vibrant mix of fashion, beauty, tech, and more all in one place.
Beyond shopping, the area boasts fine dining, historic architecture, and iconic landmarks like the Wrigley Building. It’s a lively, upscale district that captures the energy of the city. Whether browsing or buying, a stroll down the Mag Mile is a quintessential Chicago experience.
5. Ride the Ferris wheel at Navy Pier
Riding the Ferris wheel at Navy Pier offers breathtaking views of the Chicago skyline and Lake Michigan. The Centennial Wheel stands 200 feet tall, providing a smooth, enclosed ride suitable for all ages. It’s a fun and memorable way to see the city from above.
Navy Pier itself is a hub of entertainment, with shops, restaurants, and seasonal events. The Ferris wheel is its iconic centerpiece, attracting millions of visitors each year. Both thrilling and scenic, it’s a must-do for first-timers and locals alike.
6. See the animals at the free Lincoln Park Zoo
Lincoln Park Zoo is one of the oldest and most beloved zoos in the country—and it’s completely free to visit. Nestled in a scenic park near the lakefront, it houses hundreds of animals from around the world. Families and visitors of all ages enjoy its engaging exhibits and naturalistic habitats.
The zoo also offers seasonal events, educational programs, and beautiful gardens year-round. Its combination of wildlife, accessibility, and cost-free admission makes it a standout attraction. For a fun and budget-friendly outing, it’s one of Chicago’s best experiences.
7. Enjoy expansive views at 360 CHICAGO Observation Deck
The 360 CHICAGO Observation Deck, perched on the 94th floor of the John Hancock Center, offers sweeping 360-degree views of Chicago's skyline and Lake Michigan from 1,030 feet above the Magnificent Mile. On clear days, visitors can see up to four states, making it a top spot for panoramic cityscapes and breathtaking sunsets .
Beyond the views, 360 CHICAGO features TILT, a unique thrill ride that leans visitors outward at a 30-degree angle over Michigan Avenue, providing a heart-racing perspective of the city below . The experience is complemented by CloudBar, Chicago’s highest cocktail lounge, offering local craft drinks with stunning vistas. This blend of scenic beauty and adrenaline-pumping excitement makes it a must-visit attraction in the city.
8. Visit SUE, the T. rex, at the Field Museum
Visiting SUE the T. rex at Chicago’s Field Museum is a must for any history or science enthusiast. As the most complete and best-preserved Tyrannosaurus rex skeleton ever discovered, SUE offers an unparalleled glimpse into the prehistoric world. Towering at 40.5 feet long and 13 feet tall at the hips, SUE's presence is both awe-inspiring and educational.
The exhibit goes beyond the fossil itself, immersing visitors in the Late Cretaceous period through interactive displays, animations, and sensory experiences like scent stations. Recent scientific updates have enhanced the skeleton with added gastralia bones, reflecting the latest research. Celebrating its 25th anniversary, SUE continues to captivate audiences, making it a standout attraction in Chicago.
9. Take a Chicago architecture river cruise
Taking a Chicago architecture river cruise is one of the best ways to explore the city’s legendary skyline. As the boat glides along the Chicago River, expert guides share stories behind iconic buildings like the Wrigley Building and Willis Tower. The cruise offers a relaxing, immersive view of the city’s architectural evolution.
Whether you're a history buff or a first-time visitor, the river cruise provides unique perspectives not visible from the streets. Daytime and evening options add flexibility, with sunset rides offering especially stunning views. It's both entertaining and educational—perfect for all ages.
10. Bring the kids to Maggie Daley Park
Maggie Daley Park is a family-friendly oasis in downtown Chicago, designed with kids in mind. Its whimsical Play Garden features imaginative play areas like suspension bridges, giant slides, and climbing towers. The park encourages active, creative play in a safe, scenic environment.
In addition to the Play Garden, the park offers mini-golf, a skating ribbon, and picnic spots. Its location near Millennium Park and the lakefront makes it easy to include in a day of sightseeing. With so much to do, it’s a top destination for families visiting the city.
11. Griffin Museum of Science and Industry
The Griffin Museum of Science and Industry in Chicago stands as one of the largest science museums in the Western Hemisphere, captivating visitors with over 35,000 artifacts and hundreds of interactive exhibits. Highlights include the U-505 Submarine, the only German sub on display in the U.S., and the Coal Mine experience, which offers a glimpse into the depths of mining operations. These immersive exhibits provide hands-on learning opportunities that engage visitors of all ages.
Beyond its permanent exhibits, the museum hosts dynamic temporary exhibitions like "Marvel's Spider-Man: Beyond Amazing," celebrating the legacy of the iconic superhero. The museum's commitment to science education is further exemplified by its interactive displays and educational programs, fostering curiosity and critical thinking. Whether you're exploring the intricacies of robotics or marveling at the marvels of human ingenuity, the Griffin Museum offers an enriching experience that makes it a top destination in Chicago.
12. Catch a Cubs game at Wrigley Field
Catching a Cubs game at Wrigley Field is a classic Chicago experience filled with history, energy, and tradition. As the second-oldest ballpark in Major League Baseball, Wrigley offers a nostalgic charm with ivy-covered walls and hand-operated scoreboards. Fans enjoy a lively atmosphere that celebrates both the sport and the city’s deep-rooted team pride.
Even non-baseball fans find something to love, from the singing of “Take Me Out to the Ball Game” to the vibrant neighborhood of Wrigleyville. The surrounding bars, restaurants, and rooftop views create a festive game-day vibe. It’s more than a sporting event—it’s a cultural must-do in Chicago.
13. Shedd Aquarium
The Shedd Aquarium stands as one of Chicago's premier attractions, captivating visitors with its vast array of aquatic life and immersive exhibits. Home to over 32,000 animals, the aquarium offers a journey through diverse ecosystems—from the vibrant coral reefs of the Philippines in the Wild Reef exhibit to the lush environments of the Amazon Rising. Signature experiences like the Caribbean Reef's 90,000-gallon habitat provide a 360-degree view of sea turtles, sharks, and stingrays, offering both educational and awe-inspiring encounters.
Beyond its exhibits, Shedd Aquarium offers unique interactive experiences that engage visitors of all ages. Guests can participate in animal encounters, behind-the-scenes tours, and even special programs like the "Trainer for a Day," providing deeper insights into marine life and conservation efforts. With its commitment to education, conservation, and unforgettable experiences, the Shedd Aquarium remains a must-visit destination in Chicago.
14. Stroll the Chicago Riverwalk
Strolling the Chicago Riverwalk is one of the best ways to experience the city's vibrant downtown and iconic architecture. This scenic pedestrian path stretches along the Chicago River, offering views of historic buildings, bridges, and passing boats. It’s a peaceful yet lively spot perfect for walking, sightseeing, or relaxing.
The Riverwalk also features cafes, public art, kayak rentals, and outdoor seating areas. Whether enjoying a riverside meal or listening to live music, there’s always something happening. Its blend of nature, culture, and city life makes it a top attraction for visitors and locals alike.
15. Skydeck Chicago at the Willis Tower
Skydeck Chicago at the Willis Tower offers an unparalleled experience, standing as the highest observation deck in the United States. Located on the 103rd floor, it provides breathtaking panoramic views that stretch up to 50 miles on clear days, allowing visitors to see parts of Illinois, Indiana, Wisconsin, and Michigan. The journey to the top is swift and exhilarating, with elevators reaching the Skydeck in about 60 seconds .
A highlight of the Skydeck is "The Ledge," a series of glass balconies extending 4.3 feet outside the building, offering a thrilling view straight down from 1,353 feet above the city streets. These glass boxes are constructed with three layers of half-inch-thick glass, ensuring safety while providing an adrenaline-pumping experience. The Skydeck also features interactive exhibits that celebrate Chicago's rich history and culture, making it a comprehensive and memorable attraction for visitors of all ages.
16. Swim at North Avenue Beach
Swimming at North Avenue Beach is one of the best things to do in Chicago, especially during the summer months. Located in Lincoln Park, this beach offers a vibrant atmosphere with stunning views of the city skyline and Lake Michigan. The beach features a unique, ocean liner-inspired beach house that provides amenities such as restrooms, showers, and a rooftop deck for panoramic views.
Beyond swimming, North Avenue Beach offers a variety of activities, including beach volleyball, paddleboard rentals, and access to the Lakefront Trail for biking and jogging. The beach is also home to Castaways Beach Club, a popular spot for food and drinks with a lively atmosphere. With its combination of recreational options and scenic beauty, North Avenue Beach provides a quintessential Chicago summer experience.
17. See a sketch comedy show at The Second City
Seeing a sketch comedy show at The Second City is a quintessential Chicago experience, offering a blend of sharp wit, improvisation, and cultural commentary. Established in 1959, The Second City has been the launching pad for numerous comedy legends, including Tina Fey, Stephen Colbert, Steve Carell, and Keegan-Michael Key . The theater's intimate setting and dynamic performances ensure that each show is both unique and engaging, reflecting the pulse of contemporary society.
Beyond its rich history, The Second City continues to innovate, presenting new material that resonates with today's audiences. The current production, "The Best of The Second City: 65 Years of Funny," showcases a curated selection of iconic sketches reimagined for modern times. Attending a show here not only guarantees laughter but also offers a glimpse into the evolving landscape of comedic performance.
18. The Chicago Theatre
Visiting the Chicago Theatre is a must-do in Chicago due to its rich history and architectural grandeur. Opened in 1921 as the first lavish movie palace in the U.S., it was dubbed the "Wonder Theatre of the World". Its iconic six-story "C-H-I-C-A-G-O" marquee has become a symbol of the city.
The theater's French Baroque design features a grand lobby modeled after the Royal Chapel at Versailles, a majestic staircase, and a stunning auditorium adorned with murals. Today, it hosts a variety of performances, from concerts to comedy shows, offering an unforgettable experience in a historic setting. Whether attending a show or taking a guided tour, The Chicago Theatre provides a unique glimpse into the city's cultural legacy.
19. Visit the DuSable Black History Museum and Education Center
Visiting the DuSable Black History Museum and Education Center is one of the best things to do in Chicago because it offers a profound exploration of African American history and culture. Founded in 1961 by Dr. Margaret Taylor-Burroughs and her husband Charles Burroughs, it stands as the nation's oldest independent Black history museum. The museum's extensive collection includes over 15,000 artifacts, artworks, and documents that chronicle the African American experience.
The museum's exhibitions, such as "Freedom: Origin and Journey," take visitors on a journey through key periods in African American history, addressing the Transatlantic Slave Trade and the struggle for equality. Additionally, the museum offers educational programs and special events that engage the community and promote understanding of Black history and culture. With its rich history and commitment to education, the DuSable Museum provides an essential and enlightening experience for all visitors.
20. Let the kids play at the Chicago Children's Museum
Visiting the Chicago Children's Museum is one of the best things to do in Chicago for families with young children. Located at Navy Pier, the museum offers over 15 interactive exhibits designed to spark curiosity and promote learning through play. From climbing structures like the Cloud Buster to imaginative spaces like Kids Town, children can explore, create, and discover in a safe and engaging environment.
The museum's commitment to inclusivity ensures that children of all abilities can participate fully in the exhibits. With features like adjustable-height tables in the Kraft Artabounds Studio and universally accessible exhibits like Waterways, every child can enjoy the experience. Whether it's digging for "fossils" in the Dinosaur Expedition or experimenting in the Tinkering Lab, the Chicago Children's Museum provides a memorable and educational outing for families visiting the city.
