50 Things to Do in Chicago Illinois

Chicago, Illinois, is a vibrant city with a rich history, diverse culture, and countless attractions. Whether you’re visiting for the first time or you’re a local looking for new experiences, there’s always something to do in the Windy City. From world-class museums and iconic architecture to outdoor adventures and hidden gems, here are 50 must-do activities in Chicago.

1. Visit Millennium Park

Millennium Park is a must-see for anyone visiting Chicago. Home to the famous Cloud Gate sculpture (also known as “The Bean”), the park offers art, architecture, and green space right in the heart of downtown. Don’t miss the Crown Fountain and the Jay Pritzker Pavilion for outdoor concerts.

2. Explore the Art Institute of Chicago

The Art Institute of Chicago is one of the oldest and largest art museums in the United States. Its vast collection includes iconic works like Grant Wood’s American Gothic and Georges Seurat’s A Sunday on La Grande Jatte. The museum’s diverse collection spans thousands of years and multiple cultures.

3. Walk the Magnificent Mile

The Magnificent Mile is Chicago’s premier shopping district, located along Michigan Avenue. Stroll past high-end boutiques, department stores, and luxury hotels, and enjoy the stunning architecture that lines this famous street.

4. Take in the Views from the Willis Tower Skydeck

The Willis Tower (formerly the Sears Tower) is one of Chicago’s most iconic buildings. Head up to the Skydeck on the 103rd floor to experience breathtaking views of the city and Lake Michigan. For the brave, step out onto The Ledge, a glass box that extends 4.3 feet from the building.

5. Tour the Chicago Riverwalk

The Chicago Riverwalk is a scenic pathway along the Chicago River, offering beautiful views of the city’s architecture. The Riverwalk is lined with cafes, restaurants, and public art, making it a perfect spot for a leisurely stroll or a boat tour.

6. Visit the Museum of Science and Industry

The Museum of Science and Industry, located in Jackson Park, is one of the largest science museums in the world. It features interactive exhibits on a wide range of topics, including space exploration, the human body, and transportation. Highlights include the U-505 submarine and the Apollo 8 spacecraft.

7. Explore the Field Museum

The Field Museum is a world-renowned natural history museum. It’s home to “Sue,” the largest and most complete Tyrannosaurus rex skeleton ever discovered. The museum’s vast collection also includes exhibits on ancient Egypt, the evolution of life, and cultures from around the world.

8. Spend a Day at Navy Pier

Navy Pier is one of Chicago’s top tourist destinations, offering a variety of attractions for all ages. Enjoy a ride on the Centennial Wheel, visit the Chicago Children’s Museum, or catch a live performance at the Chicago Shakespeare Theater. The pier also features restaurants, shops, and seasonal events.

9. Discover the Shedd Aquarium

The Shedd Aquarium is one of the largest indoor aquariums in the world, home to over 32,000 aquatic animals. Explore exhibits that showcase marine life from the Amazon River to the Arctic Ocean, and don’t miss the daily aquatic shows featuring dolphins, sea lions, and beluga whales.

10. Visit the Adler Planetarium

The Adler Planetarium, located on the shores of Lake Michigan, is America’s first planetarium. It offers interactive exhibits, live shows in its state-of-the-art theaters, and stunning views of the Chicago skyline. The planetarium is a must-visit for astronomy enthusiasts and families alike.

11. Tour the Frank Lloyd Wright Home and Studio

Frank Lloyd Wright, one of America’s most famous architects, began his career in Chicago. Visit his home and studio in the suburb of Oak Park to learn about his early work and see the birthplace of the Prairie School of architecture. Guided tours provide insight into Wright’s innovative designs.

12. Take a Chicago Architecture River Cruise

Chicago is renowned for its architecture, and there’s no better way to see it than from the water. A Chicago Architecture River Cruise offers a guided tour of the city’s most iconic buildings, including the Tribune Tower, Marina City, and the Wrigley Building, all while cruising along the Chicago River.

13. Explore Lincoln Park Zoo

Lincoln Park Zoo is one of the oldest zoos in the United States and remains one of the few free-admission zoos. Located in the heart of Lincoln Park, the zoo is home to a wide variety of animals, from big cats and gorillas to penguins and polar bears.

14. Visit the Chicago History Museum

The Chicago History Museum offers an in-depth look at the city’s past. Exhibits cover everything from the Great Chicago Fire and the World’s Columbian Exposition to Chicago’s role in the civil rights movement and its diverse neighborhoods.

15. Walk Through Grant Park

Grant Park is known as “Chicago’s front yard,” offering 319 acres of green space in the heart of the city. The park is home to Buckingham Fountain, one of the largest fountains in the world, and hosts several major events and festivals throughout the year.

16. Enjoy a Show at the Chicago Theatre

The Chicago Theatre, with its iconic marquee, is one of the city’s most famous venues. Built in 1921, the theater hosts a variety of performances, including concerts, comedy shows, and theatrical productions. The historic interior is just as impressive as the shows on stage.

17. Visit the Museum of Contemporary Art Chicago

The Museum of Contemporary Art Chicago (MCA) is one of the largest contemporary art museums in the world. The museum’s ever-changing exhibits feature works by some of the most innovative artists of our time, alongside performances, film screenings, and public programs.

18. Explore the Garfield Park Conservatory

The Garfield Park Conservatory is one of the largest and most stunning botanical conservatories in the United States. It houses thousands of plant species across eight indoor display gardens, including a lush tropical rainforest and a desert room. The outdoor gardens are equally beautiful, especially in the spring and summer.

19. Walk the 606 Trail

The 606 is an elevated trail that stretches for 2.7 miles through several of Chicago’s neighborhoods, including Wicker Park, Bucktown, and Logan Square. Built on a former railroad line, the trail is perfect for walking, running, or biking and features art installations and green spaces along the way.

20. Attend a Cubs Game at Wrigley Field

Wrigley Field, home to the Chicago Cubs, is one of the most historic and beloved ballparks in Major League Baseball. Catching a Cubs game is a quintessential Chicago experience, whether you’re a die-hard fan or just soaking up the atmosphere of this iconic venue.

21. Visit the DuSable Museum of African American History

The DuSable Museum of African American History, located in Washington Park, is dedicated to the history, culture, and achievements of African Americans. The museum’s exhibits explore a wide range of topics, from the civil rights movement to the contributions of African American artists, scientists, and leaders.

22. Experience the Chicago Symphony Orchestra

The Chicago Symphony Orchestra (CSO) is one of the world’s leading orchestras, known for its exceptional performances and recordings. Attend a concert at Symphony Center to experience the power and beauty of classical music, conducted by some of the most renowned conductors in the world.

23. Shop at the Chicago French Market

The Chicago French Market, located in the West Loop, is an indoor market featuring over 30 vendors offering fresh produce, artisanal foods, and unique products. It’s a great spot to grab a quick bite, pick up gourmet ingredients, or enjoy a leisurely lunch.

24. Explore Chinatown

Chicago’s Chinatown is a vibrant neighborhood filled with shops, restaurants, and cultural landmarks. Visit the Chinatown Gate, explore the Chinese-American Museum, and enjoy authentic Chinese cuisine at one of the many restaurants lining Wentworth Avenue.

25. Tour the Robie House

The Robie House, located in Hyde Park, is one of Frank Lloyd Wright’s most famous works and a masterpiece of Prairie School architecture. The house is a UNESCO World Heritage site and offers guided tours that provide insight into Wright’s revolutionary design principles.

26. Visit the Chicago Cultural Center

The Chicago Cultural Center is a stunning building that hosts free art exhibits, concerts, and cultural events. The center’s interior features beautiful mosaics and the world’s largest Tiffany stained-glass dome. It’s a must-visit for anyone interested in Chicago’s cultural scene.

27. Walk Along the Lakefront Trail

The Lakefront Trail is an 18-mile path that runs along the shores of Lake Michigan, offering breathtaking views of the lake and the city skyline. The trail is popular with walkers, runners, and cyclists and connects many of the city’s beaches, parks, and cultural attractions.

28. Visit the Peggy Notebaert Nature Museum

The Peggy Notebaert Nature Museum in Lincoln Park is dedicated to nature and science. The museum features exhibits on the ecosystems of the Great Lakes region, a butterfly house with hundreds of live butterflies, and interactive displays that are perfect for children and families.

29. Explore the Chicago Botanic Garden

Located just outside the city in Glencoe, the Chicago Botanic Garden is a 385-acre living museum featuring 27 display gardens and four natural habitats. The garden is open year-round and offers a variety of seasonal events, horticultural classes, and nature walks.

30. Take a Food Tour

Chicago is known for its culinary scene, and a food tour is a great way to sample the city’s famous dishes. Whether you’re craving deep-dish pizza, Chicago-style hot dogs, or international cuisine, there’s a food tour that will take you to some of the best eateries in the city.

31. Discover Pilsen’s Street Art

The Pilsen neighborhood is known for its vibrant street art and murals, many of which reflect the area’s rich Mexican heritage. Take a self-guided walking tour to explore the colorful murals that adorn the buildings and alleys throughout the neighborhood.

32. Visit the American Writers Museum

The American Writers Museum, located on Michigan Avenue, is the first museum in the United States dedicated to the lives and works of American writers. The museum features interactive exhibits that celebrate the impact of literature on American culture and history.

33. Attend a Festival in Grant Park

Grant Park hosts some of Chicago’s biggest and most popular festivals, including the Taste of Chicago, the Chicago Blues Festival, and Lollapalooza. These events draw large crowds and offer a chance to experience Chicago’s diverse music, food, and arts scenes.

34. Take a Brewery Tour

Chicago’s craft beer scene is booming, and there are plenty of breweries to explore throughout the city. Take a brewery tour to learn about the brewing process and sample a variety of local beers. Some popular breweries include Revolution Brewing, Goose Island, and Lagunitas.

35. Visit the Chicago Children’s Museum

The Chicago Children’s Museum, located at Navy Pier, offers interactive exhibits and activities designed for children of all ages. The museum features hands-on exhibits on art, science, and imagination, making it a great destination for families with young children.

36. Explore the Newberry Library

The Newberry Library is an independent research library with a vast collection of rare books, manuscripts, and maps. The library offers free exhibitions, public programs, and tours, making it a must-visit for history buffs and book lovers.

37. Discover Andersonville

Andersonville is a charming neighborhood on the city’s North Side, known for its Swedish heritage, independent shops, and diverse dining options. Explore the Swedish American Museum, shop at unique boutiques, and enjoy a meal at one of the neighborhood’s many restaurants.

38. Visit the Pullman National Monument

The Pullman National Monument, located on Chicago’s South Side, is a historic site that tells the story of the Pullman Company and its role in American labor history. The monument includes the original Pullman factory, the Hotel Florence, and the Pullman Historic District.

39. Enjoy a Night Out in Wicker Park

Wicker Park is one of Chicago’s trendiest neighborhoods, known for its vibrant nightlife, eclectic shops, and diverse dining scene. Spend an evening exploring the neighborhood’s bars, music venues, and restaurants, and soak in the lively atmosphere.

40. Take a Gangster and Ghost Tour

Chicago’s history is filled with tales of gangsters and ghosts, and a guided tour is a great way to explore the city’s dark past. Learn about famous gangsters like Al Capone, visit haunted sites, and hear stories of the city’s most notorious events.

41. Visit the Smart Museum of Art

The Smart Museum of Art, located on the University of Chicago campus in Hyde Park, features a diverse collection of artworks from around the world. The museum’s exhibits include everything from Renaissance paintings to contemporary art, and admission is free.

42. Explore the Gold Coast Historic District

The Gold Coast Historic District is one of Chicago’s most affluent neighborhoods, known for its historic mansions and beautiful architecture. Take a stroll through the neighborhood to admire the opulent homes and visit landmarks like the Charnley-Persky House.

43. Visit the Chicago Water Tower

The Chicago Water Tower is one of the few buildings to survive the Great Chicago Fire of 1871. Located on Michigan Avenue, the Water Tower is now a symbol of the city’s resilience and is home to a small gallery showcasing local artists.

44. Experience the Music at Kingston Mines

Kingston Mines is one of Chicago’s most famous blues clubs, offering live music every night of the week. The club features two stages, with performances by some of the best blues musicians in the city. It’s a must-visit for anyone looking to experience Chicago’s legendary blues scene.

45. Visit the Oriental Institute Museum

The Oriental Institute Museum, located on the University of Chicago campus, is dedicated to the history and archaeology of the ancient Near East. The museum’s collection includes artifacts from ancient Egypt, Mesopotamia, and Persia, making it a fascinating destination for history enthusiasts.

46. Watch a Chicago Bulls NBA Game

Explore the Atrium at the United Center, where you can view the iconic Michael Jordan statue, watch a NBA basketball game and purchase official Bulls merchandise at the Madhouse Team Store.

47. Explore the Hyde Park Neighborhood

Hyde Park is home to the University of Chicago, the Museum of Science and Industry, and the Robie House. Explore the neighborhood’s historic architecture, enjoy a walk along the lakefront, and visit the local shops and restaurants.

48. Visit the International Museum of Surgical Science

The International Museum of Surgical Science, located in a historic mansion on Lake Shore Drive, offers exhibits on the history of surgery and medical science. The museum features artifacts, surgical instruments, and medical art, providing a unique and educational experience.

49. Attend a Concert at Ravinia Festival

Ravinia Festival, located just north of Chicago in Highland Park, is the oldest outdoor music festival in the United States. The festival offers a wide range of performances, including classical music, jazz, rock, and pop. Bring a picnic and enjoy a summer concert under the stars.

50. Explore the Art and Gardens at the Renaissance Society

The Renaissance Society, located on the University of Chicago campus, is a contemporary art museum that showcases cutting-edge works by emerging and established artists. The museum offers free admission and is known for its innovative exhibitions and public programs.