28 Fun Things to Do in Chicago

1. Millennium Park and Cloud Gate

Free, Parks and Gardens, Sightseeing

1 to 2 hours

Millennium Park in Chicago is a dynamic urban space offering a variety of activities for visitors. At its heart lies Cloud Gate, affectionately known as "The Bean," a stunning, mirrored sculpture by artist Anish Kapoor. This iconic piece invites endless photo opportunities as its reflective surface captures the city's skyline and the faces of those who gather around it. Beyond Cloud Gate, Millennium Park features the Jay Pritzker Pavilion, an architectural marvel designed by Frank Gehry, which hosts free concerts and events. The Lurie Garden offers a tranquil escape with its beautiful, native plantings. The Crown Fountain, with its towering glass block towers displaying digital faces, provides a playful splash zone for kids and adults alike. Visitors can also enjoy seasonal activities, such as ice skating in winter or outdoor films in summer. Millennium Park is a vibrant, cultural hub that promises a rich experience for all who visit.

2. Grant Park and Buckingham Fountain

Free, Parks and Gardens, Recreation

Half Day to Full Day

Grant Park and Buckingham Fountain in Chicago offer a plethora of activities and sights that cater to a variety of interests. Spanning over 300 acres, Grant Park is often referred to as "Chicago's front yard," featuring beautifully manicured gardens, walking paths, and open spaces perfect for picnics or leisurely strolls. You can explore iconic landmarks like the Art Institute of Chicago and the Museum Campus, which includes the Field Museum, Shedd Aquarium, and Adler Planetarium. At the heart of Grant Park lies Buckingham Fountain, one of the largest fountains in the world. During the warmer months, you can catch its spectacular water shows, which are choreographed to music and feature evening light displays. The nearby Lakefront Trail offers a scenic route for biking, jogging, or simply taking in views of Lake Michigan. Whether you're interested in cultural attractions, outdoor activities, or simply relaxing amid stunning urban landscapes, Grant Park and Buckingham Fountain provide a rich and diverse experience.

3. Art Institute of Chicago

Museums

2 hours to Half Day

The Art Institute of Chicago is a world-renowned museum that offers a diverse array of activities for visitors. You can explore its vast collection of artwork spanning thousands of years, from ancient artifacts to contemporary masterpieces. Noteworthy highlights include iconic pieces like Grant Wood's "American Gothic" and Georges Seurat's "A Sunday on La Grande Jatte." The museum also features an impressive collection of Impressionist and Post-Impressionist paintings, with works by artists such as Claude Monet, Vincent van Gogh, and Edgar Degas. In addition to its permanent collection, the Art Institute hosts rotating special exhibitions, offering fresh perspectives and unique cultural experiences. You can also participate in educational programs, guided tours, and art-making workshops suitable for all ages. For a more relaxed visit, enjoy a meal at one of the museum's cafes or shop for unique souvenirs at the museum store. Whether you're an art novice or a seasoned aficionado, the Art Institute of Chicago provides a rich, immersive experience in the world of art.

4. The Magnificent Mile

Free, Cafes, Neighborhood/Area, Shopping

2 hours to Half Day

The Magnificent Mile in Chicago is a bustling, vibrant stretch of Michigan Avenue offering a diverse array of activities. Renowned for its upscale shopping, visitors can explore luxury boutiques, flagship stores, and high-end retail outlets. Culinary enthusiasts will delight in the myriad of dining options, from gourmet restaurants to trendy cafes and iconic eateries. Cultural attractions abound, including the Museum of Contemporary Art and historic landmarks like the Wrigley Building and the Tribune Tower. For a touch of nature amidst the urban landscape, the nearby Chicago Riverwalk and Oak Street Beach provide scenic spots for relaxation and recreation. Architectural tours, both on foot and by boat, offer insights into the city’s storied skyline. During holidays, the area transforms with festive lights and decorations, enhancing its allure. Whether you’re shopping, dining, or sightseeing, The Magnificent Mile promises an unforgettable experience in the heart of Chicago.

5. Navy Pier

Amusement Parks, Free, Sightseeing

2 hours to Half Day

Navy Pier, located on the shores of Lake Michigan in Chicago, is a vibrant entertainment destination offering a plethora of activities for all ages. You can start by taking a leisurely walk along the pier to enjoy stunning lake and city skyline views. For thrill-seekers, the Centennial Wheel provides an exhilarating ride with panoramic vistas. Families can explore the Chicago Children's Museum, packed with interactive exhibits, or catch a show at the Chicago Shakespeare Theater. During warmer months, the pier's beer garden and outdoor restaurants are perfect for a relaxing meal with waterfront views. Seasonal events like fireworks, live music, and festivals add to the lively atmosphere. Don't miss the Crystal Gardens, an indoor botanical garden that offers a serene escape. With its blend of attractions, dining options, and breathtaking scenery, Navy Pier ensures a memorable experience for everyone.

6. Lincoln Park Zoo

Zoos and Aquariums, Free

2 hours to Half Day

Lincoln Park Zoo in Chicago offers an array of engaging activities and attractions for visitors of all ages. One can explore the diverse animal habitats, which are home to over 1,000 animals from around the world, including big cats, primates, reptiles, and birds. The zoo features a variety of exhibits, such as the Regenstein Center for African Apes and the Kovler Lion House, providing up-close views and educational insights. Families can enjoy the Pritzker Family Children's Zoo, which focuses on North American wildlife and offers interactive elements for kids. The zoo also hosts seasonal events, such as ZooLights during the winter holidays, where the grounds are adorned with festive lights and decorations. Visitors can relax in the beautiful gardens or have a picnic in designated areas. The zoo's cafes and gift shops offer refreshments and souvenirs. Best of all, Lincoln Park Zoo is free to the public, making it an accessible and enriching experience for everyone.

7. 360 CHICAGO Observation Deck

Sightseeing

1 to 2 hours

360 CHICAGO Observation Deck, located on the 94th floor of the John Hancock Center, offers an unparalleled view of Chicago's skyline, Lake Michigan, and up to four neighboring states on clear days. Visitors can experience breathtaking 360-degree views from 1,030 feet above the Magnificent Mile. One of the deck's standout attractions is TILT, an exhilarating ride that tilts guests outward from the building, providing a unique downward-facing perspective of the city below. Additionally, interactive multimedia exhibits offer insights into Chicago's rich history, architecture, and culture. For a more relaxed experience, visitors can enjoy a drink or snack at BAR 94, the highest bar in Chicago, while soaking in the stunning vistas. Whether you're a tourist or a local, 360 CHICAGO promises an unforgettable experience, combining thrilling adventures with educational opportunities and unparalleled city panoramas.

8. The Field Museum

Museums

2 hours to Half Day

The Field Museum in Chicago offers an array of captivating experiences for visitors of all ages. As you step inside, you are greeted by Sue, the largest and most complete T. rex ever discovered, setting the stage for an exciting journey through natural history. Explore the museum’s extensive exhibits, including the Ancient Egypt exhibit, where you can see real mummies and artifacts, and the evolving Planet exhibit, which showcases Earth's geological history and biodiversity. Don't miss the Grainger Hall of Gems, featuring stunning precious stones and intricate jewelry, or the Cyrus Tang Hall of China, which delves into thousands of years of Chinese history and culture. Interactive displays in the Evolving Planet exhibit provide insights into the process of evolution and the diversity of life on Earth. With rotating special exhibits, educational programs, and hands-on activities, The Field Museum offers a dynamic and enriching experience that combines education with adventure.

9. Chicago Architecture River Cruise

Tours, Sightseeing

1 to 2 hours

The Chicago Architecture River Cruise offers an unforgettable journey through the Windy City's rich architectural heritage. As you glide along the Chicago River, expert guides provide engaging commentary on over 40 landmark buildings, offering insights into the history, design, and architects behind Chicago's iconic skyline. You'll marvel at the striking contrast between historic structures like the Wrigley Building and modern masterpieces such as the Aqua Tower. The cruise provides a unique vantage point to appreciate the city's diverse architectural styles, from Art Deco to Postmodern. The leisurely pace allows ample time for photography, ensuring you capture the essence of Chicago's urban beauty. Whether you're an architecture enthusiast or simply looking to enjoy a scenic tour, the Chicago Architecture River Cruise delivers an educational and visually stunning experience that highlights why Chicago is considered a global architectural capital.

10. Maggie Daley Park

Free, Parks and Gardens, Recreation

1 to 2 hours

Maggie Daley Park, nestled in the heart of downtown Chicago, offers a vibrant array of activities suitable for all ages. The park is home to the whimsical Play Garden, a dreamscape for children with its imaginative slides, climbing structures, and splash pads. Adventure-seekers can challenge themselves on the Climbing Wall, which boasts routes for both beginners and seasoned climbers. The Skating Ribbon, a unique path that winds through the park, provides a picturesque setting for ice skating in winter and rollerblading or scootering in warmer months. For those looking to relax, the serene Cancer Survivors’ Garden offers a peaceful retreat with beautiful landscaping and reflective spaces. Additionally, the park’s lush lawns and picnic groves are perfect for a leisurely afternoon, while the mini-golf course adds a fun twist to family outings. Maggie Daley Park seamlessly blends recreation, relaxation, and scenic views, making it a must-visit urban oasis.

11. Griffin Museum of Science and Industry

Museums

2 hours to Half Day

The Griffin Museum of Science and Industry offers a captivating blend of educational and interactive experiences for visitors of all ages. You can explore a variety of hands-on exhibits that delve into fascinating topics such as physics, chemistry, and engineering. One highlight is the state-of-the-art planetarium, where you can embark on a cosmic journey through the universe, learning about stars, planets, and galaxies. The museum's innovation lab allows you to engage in DIY science projects and experiments, fostering creativity and critical thinking. Additionally, you can attend live demonstrations and workshops that showcase cutting-edge scientific advancements and industrial technologies. For history enthusiasts, the museum provides intriguing exhibits on the evolution of industrial machinery and its impact on society. The Griffin Museum of Science and Industry is a perfect destination for those looking to ignite their curiosity and deepen their understanding of the world through science and technology.

12. Wrigley Field

Sports, Tours

2 hours to Half Day

Wrigley Field, located in Chicago, is one of Major League Baseball's most iconic ballparks. As the home of the Chicago Cubs, it offers an unforgettable experience for baseball fans and visitors alike. You can catch a thrilling Cubs game, soaking in the historic atmosphere and enjoying the timeless charm of the ivy-covered outfield walls. Beyond the games, you can take a guided tour of the stadium to explore its rich history, including the dugouts, press box, and even the chance to step onto the field. On non-game days, Wrigley Field frequently hosts concerts and other events, adding to its vibrant appeal. The surrounding Wrigleyville neighborhood is bustling with lively bars, restaurants, and shops, perfect for pre- or post-game entertainment. Whether you're a die-hard baseball fan or just looking for a unique Chicago experience, Wrigley Field offers something special for everyone.

13. Shedd Aquarium

Zoos and Aquariums

2 hours to Half Day

Shedd Aquarium in Chicago offers a captivating underwater experience with a wide array of activities and exhibits. You can explore the stunning aquatic environments, from the Amazon River to coral reefs. Witness the vibrant marine life, including sharks, dolphins, sea turtles, and various exotic fish. The Oceanarium provides an up-close look at beluga whales and sea otters. Interactive exhibits like "Stingray Touch" allow you to feel the smooth texture of stingrays. Don't miss the daily aquatic shows featuring dolphins and sea lions, showcasing their intelligence and agility. The 4D Experience Theater adds an extra sensory dimension to your visit with engaging films. Educational programs and behind-the-scenes tours offer deeper insights into marine conservation efforts. Shedd Aquarium is not just an attraction but a hub for learning and fostering a connection with our planet’s oceans and rivers.

14. The Chicago Riverwalk

Free, Parks and Gardens

1 to 2 hours

The Chicago Riverwalk is a vibrant, pedestrian-friendly promenade that stretches along the south bank of the Chicago River, offering a multitude of activities for visitors of all ages. You can start your day with a scenic stroll or a bike ride along the path, taking in stunning views of the city's iconic architecture. Outdoor enthusiasts can rent kayaks or take a guided boat tour to explore the river from a different perspective. For a more leisurely experience, relax at one of the many waterfront cafes and restaurants, where you can savor delicious local cuisine while watching boats drift by. Art lovers will appreciate the public art installations and occasional live performances. The Riverwalk also features green spaces and quiet spots perfect for picnicking or simply unwinding. Throughout the year, the area hosts various events and festivals, making it a dynamic and ever-changing destination.

15. Skydeck Chicago at the Willis Tower

Sightseeing

1 to 2 hours

Skydeck Chicago at the Willis Tower offers an exhilarating experience that showcases the city's stunning skyline from 1,353 feet above ground. Upon arrival, you can explore the interactive exhibits detailing the history and architecture of Chicago and the Willis Tower. The main attraction is The Ledge, a series of glass boxes extending 4.3 feet from the Skydeck, providing a thrilling opportunity to step out and look straight down at the bustling streets below. You'll also have panoramic views of up to four states on a clear day. For a unique perspective, visit during sunset or nighttime to see the city lights twinkle. Additionally, the Skydeck often hosts special events and seasonal activities, enhancing your visit with unique experiences. Whether you're a local or a tourist, Skydeck Chicago offers unforgettable views and photo opportunities that capture the essence of the Windy City.

16. North Avenue Beach

Beaches, Free

2 hours to Half Day

North Avenue Beach, located in the heart of Chicago along Lake Michigan, is a vibrant destination that offers a variety of activities for visitors. Whether you're looking to relax or engage in some active fun, this popular beach has something for everyone. The expansive sandy shore is perfect for sunbathing or building sandcastles, while the clear waters invite you to take a refreshing swim. For those who enjoy water sports, paddleboarding, kayaking, and jet skiing rentals are readily available. Fitness enthusiasts can take advantage of the beach's volleyball courts or join one of the many fitness classes offered, such as yoga or beach boot camps. The scenic lakefront path is ideal for jogging, biking, or rollerblading, providing stunning views of the Chicago skyline. When hunger strikes, head to Castaways Bar & Grill, a lively spot housed in a ship-shaped building where you can enjoy food and drinks with a fantastic view. Whether you're there to relax or get active, North Avenue Beach is a must-visit spot in Chicago.

17. The Second City

Entertainment and Nightlife

1 to 2 hours

The Second City in Chicago offers a vibrant mix of comedic entertainment, workshops, and dining experiences. Renowned as a premier comedy institution, visitors can enjoy live performances featuring sketch comedy, improv, and stand-up acts that have launched numerous famous careers. The Mainstage Theatre and the e.t.c. Stage are popular for their rotating shows that combine sharp wit with social commentary. For those looking to delve deeper, the Second City Training Center provides classes in improvisation, writing, and acting, catering to both beginners and advanced students. The center's workshops are a great way to enhance your comedic skills or simply have fun in a supportive environment. After the show or class, you can relax at 1959 Kitchen & Bar, which offers a menu filled with delicious food and drinks. Whether you're a comedy enthusiast or just looking for a fun night out, The Second City promises an unforgettable experience full of laughter and creativity.

18. The Chicago Theatre

Entertainment and Nightlife, Sightseeing

1 to 2 hours

The Chicago Theatre, an iconic landmark located in the heart of downtown Chicago, offers a rich array of entertainment options. As a premier venue, it hosts an eclectic mix of performances including Broadway shows, concerts, comedy acts, and special events. Stepping inside, you'll be captivated by its stunning French Baroque architecture and the grandeur of its six-story auditorium, which boasts a majestic stage and excellent acoustics. Visitors can attend live performances by renowned artists and enjoy classic theater productions. For those interested in the venue's history, guided tours provide an insightful glimpse into its storied past, architectural beauty, and backstage secrets. The Chicago Theatre's marquee, one of the most photographed in the city, is a must-see for any visitor. Surrounding the theater, the vibrant downtown area offers plenty of dining and shopping options, making it easy to plan a full day or evening around your visit to this cultural gem.

19. Chicago Children's Museum

Museums

1 to 2 hours

The Chicago Children's Museum, located at Navy Pier, offers a variety of engaging and educational activities for children and families. Visitors can explore interactive exhibits designed to inspire learning through play. Highlights include the "Dinosaur Expedition," where kids can dig for fossils and learn about prehistoric creatures, and the "WaterWays" exhibit, which allows children to experiment with water flow and physics. The "Kids Town" area mimics a bustling cityscape, complete with a grocery store, CTA bus, and a fire station, encouraging imaginative role play. Art enthusiasts can unleash their creativity in the "Tinkering Lab" and "Art Studio," where various materials and tools are available for crafting and building projects. The museum also offers special programs, workshops, and performances throughout the year, ensuring every visit is unique. With its diverse range of activities, the Chicago Children's Museum provides a fun and enriching environment for kids to explore, discover, and learn.

20. American Writers Museum

Museums

1 to 2 hours

The American Writers Museum in Chicago offers a vibrant, interactive experience celebrating the diverse voices and rich history of American literature. Visitors can explore thematic exhibits that delve into the lives and works of iconic writers, from Mark Twain to Maya Angelou. The "Nation of Writers" gallery showcases pivotal literary contributions across different eras, while the "Surprise Bookshelf" features rotating displays of beloved classics and modern works. Interactive touchscreens invite guests to delve deeper into authors' biographies and literary styles, and the "Word Waterfall" presents a mesmerizing visual display of influential quotes. The "Children’s Literature Gallery" caters to younger audiences with engaging activities and storybook displays. Special events, such as author readings, writing workshops, and panel discussions, provide unique opportunities for literary immersion. Overall, the museum offers a dynamic and educational experience, fostering a deeper appreciation for the art of writing and its impact on American culture.

21. DuSable Black History Museum and Education Center

Museums

1 to 2 hours

The DuSable Black History Museum and Education Center, located in Chicago, offers a rich and immersive experience into the African American cultural heritage and history. Visitors can explore a wide range of exhibits that showcase the contributions and struggles of African Americans throughout history. The museum features permanent and rotating exhibitions, including art, historical artifacts, and multimedia presentations, providing a comprehensive view of Black history from the African diaspora to contemporary times. Educational programs and workshops are also available, catering to all age groups, from children to adults. These programs include lectures, film screenings, and interactive activities that delve deeper into specific themes and figures in Black history. The museum often hosts cultural events, such as musical performances, book readings, and community discussions, fostering a vibrant cultural exchange and engagement. Additionally, the museum's gift shop offers a variety of books, artwork, and memorabilia, allowing visitors to take a piece of history home with them.

22. Adler Planetarium

Museums

2 hours to Half Day

The Adler Planetarium, located in Chicago, offers a captivating blend of astronomy and space exploration. Visitors can immerse themselves in the wonders of the universe through its state-of-the-art sky shows, which project stunning visuals of stars, planets, and galaxies in a domed theater. The planetarium's exhibits delve into the history of astronomy, showcasing ancient astronomical tools and modern advancements. Interactive displays and hands-on activities, such as the Community Design Lab, allow guests to engage with scientific concepts and experiment with space-related technologies. The Grainger Sky Theater offers an awe-inspiring experience with its 8K resolution and cutting-edge sound system. The Adler also hosts special events, lectures, and workshops that cater to both amateur stargazers and seasoned astronomers. With its prime lakefront location, the planetarium provides breathtaking views of the Chicago skyline, making it a perfect spot for both learning and leisure.

23. Offbeat Street Art Tour

Tours, Sightseeing

2 hours to Half Day

The "Offbeat Street Art Tour" offers an immersive exploration of urban creativity, guiding you through vibrant neighborhoods adorned with eclectic murals, thought-provoking graffiti, and hidden art installations. As you stroll through the city’s less-traveled streets, expert guides share the stories behind the artworks and the artists, revealing the cultural and social messages embedded in each piece. You’ll discover how local and international artists transform public spaces into dynamic art galleries, often highlighting pressing social issues or celebrating community heritage. The tour also provides opportunities to witness live street art in the making, offering a behind-the-scenes look at the techniques and materials used by contemporary street artists. Along the way, you might visit artist studios or pop-up galleries, adding an interactive dimension to your experience. Perfect for art enthusiasts and curious explorers alike, the "Offbeat Street Art Tour" is a unique way to see the city through the lens of its most creative minds.

24. The Green Mill

Entertainment and Nightlife

2 hours to Half Day

The Green Mill, located in Chicago, is a historic jazz club that offers a vibrant and nostalgic experience for music lovers. Stepping into The Green Mill is like traveling back in time to the Prohibition era, with its classic speakeasy ambiance and vintage decor. The club is renowned for its live jazz performances, featuring both local talents and internationally acclaimed artists. You can enjoy a variety of jazz styles, from traditional and swing to bebop and modern jazz, ensuring there's something for every jazz aficionado. The intimate setting allows you to get up close and personal with the performers, creating an engaging and immersive experience. In addition to the music, The Green Mill offers a well-stocked bar with a selection of cocktails, wines, and spirits. Patrons can sip on their favorite drinks while soaking in the rich, melodic tunes. Whether you're a jazz enthusiast or just looking for a unique night out, The Green Mill provides an unforgettable atmosphere filled with history and exceptional music.

25. Garfield Park Conservatory

Free, Parks and Gardens

1 to 2 hours

Garfield Park Conservatory in Chicago is one of the largest and most stunning conservatories in the United States, offering a lush, year-round escape into nature. Visitors can explore a variety of themed plant collections housed in beautiful glass structures, including the Palm House, Fern Room, and Desert House. Each room showcases unique ecosystems with diverse plant species from around the world. The conservatory also features outdoor gardens, such as the City Garden and Monet Garden, perfect for leisurely strolls or quiet reflection. Engage in educational programs and workshops on gardening, sustainability, and plant care, suitable for all ages. Families can enjoy interactive exhibits and seasonal events, like the Spring Flower Show or holiday-themed displays. Don't miss the chance to participate in guided tours, which provide deeper insights into the conservatory's history and botanical treasures. Whether you're a plant enthusiast or simply seeking tranquility, Garfield Park Conservatory offers a delightful experience for everyone.

26. The Richard H. Driehaus Museum

Museums, Historic Homes/Mansions

1 to 2 hours

The Richard H. Driehaus Museum, located in a meticulously restored 19th-century mansion in Chicago, offers a captivating journey into the Gilded Age. Visitors can explore the opulent interiors, adorned with lavish furnishings, stained glass, and intricate woodwork that reflect the grandeur of the period. The museum's exquisite collection includes fine and decorative arts, with a particular emphasis on the works of Louis Comfort Tiffany. In addition to the permanent exhibits, the museum hosts rotating special exhibitions that delve into various aspects of art, culture, and history. Engaging guided tours provide deeper insights into the mansion's architecture and the stories behind its treasures. The museum also offers a variety of educational programs, lectures, and events that cater to diverse interests. A visit to the Driehaus Museum is a step back in time, offering a rich, immersive experience of America's opulent past.

27. Chicago Cultural Center

Museums, Free

1 to 2 hours

The Chicago Cultural Center, located in the heart of downtown Chicago, is a vibrant hub for arts and culture. As one of the city's most iconic landmarks, it offers a variety of free public events and exhibitions. Visitors can explore stunning art galleries featuring contemporary works from local and international artists. The building itself is an architectural marvel, boasting the world's largest Tiffany stained-glass dome and intricate mosaics. Attend a live performance in the Preston Bradley Hall, where concerts, theater productions, and dance performances frequently take place. The center also hosts informative lectures, film screenings, and family-friendly workshops. For those interested in history, guided tours provide fascinating insights into the building's rich past and design. Whether you're an art aficionado, history buff, or simply looking to experience Chicago's cultural scene, the Chicago Cultural Center offers a diverse array of activities to engage and inspire.

28. University of Chicago

Free, Neighborhood/Area, Tours, Sightseeing

1 to 2 hours

The University of Chicago offers a wealth of opportunities for intellectual and personal growth. Academically, it is renowned for its rigorous curriculum and strong emphasis on critical thinking across diverse fields such as economics, law, and the sciences. Students can engage in groundbreaking research alongside esteemed faculty, contributing to innovations and scholarly advancements. Beyond academics, the vibrant campus life includes over 400 student organizations, ranging from cultural clubs to intramural sports teams, ensuring there's something for everyone. The university's location in the heart of Chicago provides easy access to the city's rich cultural scene, including world-class museums, theaters, and dining experiences. The picturesque Hyde Park neighborhood, where the campus is situated, offers a blend of historic charm and modern amenities. Students can explore the lush greenery of the Midway Plaisance and the nearby lakefront. Whether you're attending thought-provoking lectures, participating in dynamic student groups, or enjoying the city's diverse attractions, the University of Chicago provides a stimulating environment for both academic and personal development.