Things to do

Chicago's Endless Charm: Discover 50 Best Things to Do in the Windy City

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With world-class cultural institutions, fabulous culinary scenes, nature, and cultural events and festivals, Chicago as a travel destination has a lot to offer. Whether you are interested in sports, museums, food, or water-based activities, the Windy City has it all.

Famous for its architecture, you can take guided tours to learn about the city's buildings and history. Interested in food? It has everything from deep-dish pizza to Chicago-style hot dogs. Here are the best things to do in Chicago to explore the city.

1. Take A Stroll Along The Magnificent Mile

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The Magnificent Mile is a famous stretch of road located on Michigan Avenue. The mile-long stretch is lined with luxury boutiques, department stores, and flagship stores of renowned brands such as Gucci, Louis Vuitton, and Tiffany & Co. 

As you walk along the Magnificent Mile, you'll also come across beautiful parks and green spaces. Magnificent Mile is also home to several iconic landmarks and attractions.

2. Visit Millennium Park To See The Cloud Gate Sculpture

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Millennium Park's most famous attraction is the Cloud Gate sculpture, also known as "The Bean." This iconic piece of art was created by British artist Anish Kapoor and was unveiled in 2006.

This stunning stainless steel structure measures 33 feet high, 42 feet wide, and 66 feet long. Its seamless mirror-like surface reflects the surrounding skyline, making it a popular spot for photography.

Address: 201 E Randolph St

3. Explore the Art Institute of Chicago

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Visiting the Art Institute of Chicago is a must during your trip to Chicago. It is one of the oldest and largest art museums in the United States, founded in 1879. The museum is known for its extensive collection, which spans thousands of years.

It houses a diverse range of art, including paintings, sculptures, prints, drawings, photography, textiles, and decorative arts. Some of the most famous artworks include Vincent van Gogh's "The Bedroom," and Pablo Picasso's "The Old Guitarist."

Address: 111 S Michigan Ave

4. Take An Architectural Boat Tour On The Chicago River

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This architectural tour takes place on a boat that navigates along the Chicago River, offering stunning views of the city's skyline and its famous buildings. It is not only informative but also offers stunning photo opportunities.

The tour is led by knowledgeable guides who provide interesting insights into the history and significance of the architectural landmarks. They highlight notable buildings such as the Willis Tower, the Tribune Tower, the Wrigley Building, and the Marina City Towers.

5. Enjoy A Chicago-style Deep-dish Pizza

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Chicago-style deep-dish pizza is a type of pizza in Chicago that is known for its thick, buttery crust, generous amount of cheese, and chunky tomato sauce on top. While it may not be for everyone's taste, it is definitely worth trying.

Some popular Chicago deep-dish pizza establishments include Lou Malnati's, Giordano's, and Gino's East. These restaurants have been serving up this iconic style of pizza for decades.

6. Catch A Game At Wrigley Field

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Wrigley Field is the home of the Chicago Cubs, one of the oldest and most beloved teams in Major League Baseball. It has a seating capacity of over 41,000 and is famous for its lively atmosphere and passionate fan base.

In addition to baseball games, Wrigley Field also hosts concerts and other events throughout the year. Fans from all over the world visit to experience the historic ballpark and enjoy the vibrant Wrigleyville neighborhood surrounding it.

Address: 1060 W Addison St

7. Visit The Field Museum Of Natural History

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The Field Museum of Natural History is one of the largest natural history museums in the world. It was founded in 1893 as part of the World's Columbian Exposition.

The museum houses over 40 million specimens and artifacts, including Sue, the largest and most complete Tyrannosaurus rex skeleton ever discovered. It also features extensive collections in anthropology, botany, geology, paleontology, and zoology.

Address: 1400 S Lake Shore Dr

8. Explore the Shedd Aquarium

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The Shedd Aquarium is one of the largest indoor aquariums in the world and houses over 32,000 animals. It features various exhibits that showcase different aquatic ecosystems and animal species.

Some of the highlights include the Amazon Rising exhibit, which replicates the Amazon rainforest and features piranhas, anacondas, and river otters. The Wild Reef exhibit showcases a coral reef ecosystem with sharks, rays, and other tropical fish.

Address: 1200 S DuSable Lk Shr Dr

9. Take A Walk Along Navy Pier

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Navy Pier is a 3,300-foot-long pier that extends into Lake Michigan and offers stunning views of the city skyline. As you start your walk, you'll pass by the iconic Navy Pier Ferris wheel, known as the Centennial Wheel. 

Continuing along the pier, you'll find a variety of shops, restaurants, and entertainment options. You can browse through unique boutiques, grab a bite to eat at one of the many restaurants or enjoy live music performances at the outdoor stage.

Address: 600 E Grand Ave

10. Visit The Museum Of Science And Industry

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The Museum of Science and Industry (MSI) features a wide range of exhibits and displays that cover various scientific disciplines. The museum is also home to the Omnimax Theater, which features a five-story, domed screen and shows.

Some of the permanent exhibits include the U-505 Submarine, where visitors can explore a captured German U-boat from World War II, and the Science Storms exhibit, which explores the principles of physics through interactive displays.

Address: 5700 S DuSable Lk Shr Dr

11. Check Out The Views From The Willis Tower Skydeck

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From the Willis Tower Skydeck, you can get a panoramic view of Chicago's famous skyline, with its impressive collection of skyscrapers. The view includes landmarks like the John Hancock Center, the Trump Tower, and the Aon Center.

One of the fun things to do in the Chicago, the Skydeck provides a unique vantage point to see the vast expanse of Lake Michigan. On a clear day, the lake appears endless, with its sparkling blue waters stretching out to the horizon.

Address: 233 S Wacker Dr

12. Explore The Lincoln Park Zoo

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Lincoln Park Zoo is one of the oldest zoos in North America and covers 35 acres of land within Lincoln Park. The zoo is home to over 200 species of animals, including lions, tigers, gorillas, penguins, and reptiles.

In addition to the animal exhibits, Lincoln Park Zoo also features a carousel, a train ride, and a paddleboat lake. There are also several dining options within the zoo, including cafes and food stands.

13. Take A Bike Ride Along Lake Michigan On The Lakefront Trail

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The Lakefront Trail is a popular bike path that stretches along the scenic Lake Michigan shoreline in Chicago. It offers breathtaking views of the lake, city skyline, and various landmarks along the way.

Start at the northernmost point of the trail at Ardmore Beach. As you ride further south, you will pass by popular beaches and continue riding south, passing by the beautiful Lincoln Park. As you approach downtown Chicago, you will pass by the iconic Navy Pier and after leaving Navy Pier, continue southbound along the trail.

14. Attend A Live Performance At The Chicago Theatre

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The Chicago Theatre, also known as the "Wonder Theatre of the World," is a historic landmark and iconic venue. Its iconic marquee and beautiful architecture make it a must-visit destination for anyone exploring.

Throughout its history, the Chicago Theatre has hosted a wide range of performances, including live concerts, Broadway shows, comedy acts, and film screenings. Many legendary artists and performers have graced its stage, including Frank Sinatra, Ella Fitzgerald, Louis Armstrong, and Benny Goodman.

Address: 175 N State St

15. Visit The Chicago Cultural Center

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The Chicago Cultural Center is known for its stunning architecture and serves as a hub for cultural and artistic activities in the city. The building features a grand staircase, marble columns, and intricate mosaics, making it a popular attraction for architecture enthusiasts.

It hosts a wide range of events and exhibitions, including concerts, dance performances, art exhibitions, and lectures. The center aims to showcase and promote the arts and culture of Chicago, providing free access to many of its programs.

Address: 78 E Washington St

16. Explore The Garfield Park Conservatory

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Garfield Park Conservatory is a botanical garden and one of the largest conservatories in the United States, covering an area of 4.5 acres. It was opened in 1908 and features a collection of plants from around the world, including tropical, desert, and temperate plants.

The conservatory is divided into several themed rooms, such as the Palm House, the Fern Room, the Desert House, and the Aroid House. In addition to indoor exhibits, it also has outdoor gardens and a children's garden.

Address: 300 N Central Park Ave

17. Attend A Concert At The Jay Pritzker Pavilion

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The Jay Pritzker Pavilion is a world-renowned outdoor concert venue located in Millennium Park. The venue hosts a wide variety of concerts throughout the year, ranging from classical and jazz performances to popular music acts.

Attending a concert at the Jay Pritzker Pavilion is a unique experience due to its open-air design. The venue can accommodate up to 11,000 people, with seating available in both fixed seats and on the Great Lawn.

Address: 201 E Randolph St

18. Take A Segway Tour Of The City

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A Segway tour of Chicago is a unique and fun way to explore the city's top attractions. It allows you to cover more ground than walking, while still being able to enjoy the sights and sounds of the city up close.

During the Segway tour, you will be provided with a Segway personal transporter, which is a self-balancing electric vehicle. Before the tour begins, you will receive a brief training session on how to operate the Segway, ensuring that you feel comfortable and confident riding it.

19. Explore the Museum of Contemporary Art

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The Museum of Contemporary Art (MCA) is dedicated to showcasing the work of living artists. It houses a vast collection of contemporary art, including paintings, sculptures, photography, video art, and installations.

If you are looking for things to do in the city of Chicago, spend an afternoon looking at exhibits at MCA. The museum's collection includes works by renowned artists such as Andy Warhol, Frida Kahlo, Jackson Pollock, and Cindy Sherman, among many others.

Address: 220 E Chicago Ave

20. Visit The Adler Planetarium

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The Adler Planetarium is a public museum and planetarium founded in 1930. It offers a wide range of exhibits and programs that explore the wonders of the universe. It also houses a collection of historical astronomical instruments and artifacts. 

Visitors can explore interactive exhibits on topics such as space exploration, astronomy, and the history of the universe. One of the main attractions is its state-of-the-art sky theater, which features immersive shows that take visitors on virtual journeys through space.

Address: 1300 S DuSable Lk Shr Dr

21. Take A Walk Through The Historic Neighborhood Of Wicker Park

Wicker Park, located in the West Town community area, is known for its vibrant arts and culture scene, trendy boutiques, and diverse dining options. It has a rich history, with many of its buildings dating back to the late 19th and early 20th centuries.

The neighborhood is home to numerous art galleries, theaters, and music venues, making it a hub for the city's creative community. The Flat Iron Arts Building is a notable landmark in Wicker Park, housing numerous artist studios and galleries.

22. Explore The Chicago History Museum

The Chicago History Museum has a vast collection of artifacts, documents, photographs, and other historical items that showcase the city's history. The rotating exhibits cover various aspects of Chicago's history, culture, and people.

The museum's permanent exhibits cover a wide range of topics, including the city's founding and early history, the Great Chicago Fire of 1871, the World's Columbian Exposition of 1893, and the city's role in various historical events such as the Civil Rights Movement.

Address: 1601 N Clark St

23. Sample A Variety Of Cuisines At Chicago Food Truck Festivals

Chicago is known for its vibrant food truck scene, and there are several food truck festivals held throughout the year in the city. Chicago Food Truck Festival is one of the largest food truck festivals in the city, featuring a wide variety of food trucks offering different cuisines. 

While not exclusively a food truck festival, Taste of Chicago is one of the largest food festivals in the city and features a section dedicated to food trucks. Chicago Food Truck Social brings together food trucks from all over the city.

24. Relax On The Oak Street Beach

Oak Street Beach offers beautiful views of the city skyline and a wide sandy shoreline. The water is generally clean and safe for swimming, although lifeguards are only on duty during the summer months.

Visitors can even relax and sunbathe here. The beach also has volleyball courts, a bike path, and a beach house with restrooms and concessions. Visitors can rent beach chairs, umbrellas, and paddleboards from nearby rental services.

25. Visit the Peggy Notebaert Nature Museum

The Peggy Notebaert Nature Museum is a natural history museum and part of the Chicago Academy of Sciences. It focuses on the natural history and ecology of the Midwest region.

The museum was founded in 1857 and has since become a prominent institution for environmental education and conservation. The museum features a variety of exhibits that showcase the biodiversity of the Midwest, including displays of native plants, animals, and ecosystems.

Address: 2430 N Cannon Dr

26. Attend A Live Jazz Performance At A Local Jazz Club

If you're looking to attend a live jazz performance at a local jazz club in Chicago, there are several options to choose from. Green Mill Cocktail Lounge, located in the Uptown area is a historic jazz club that features a vintage ambiance and hosts live jazz performances every night.

Andy's Jazz Club in the River North neighborhood, offers live jazz music seven nights a week. Jazz Showcase, located in the South Loop, offers live performances every night and has a cozy atmosphere perfect for enjoying the music.

27. Attend A Live Comedy Show At The Second City

Some of the fun events to do in Chicago include watching a live comedy show. The Second City is a world-renowned comedy theater known for its improvisational style and talented performers. 

At The Second City, you can expect to experience a live comedy show like no other. The theater offers a variety of shows throughout the year, ranging from sketch comedy to improv performances.

Address: 1608 N Wells St f4

28. Enjoy Live Blues Performances At Buddy Guy's Legends

Buddy Guy's Legends is a renowned blues club located in Chicago, Illinois. The club offers live blues performances by both established and up-and-coming blues artists.

The live performances at Buddy Guy's Legends showcase a variety of blues styles, from traditional Chicago blues to contemporary blues-rock. You can expect to hear soulful vocals, blistering guitar solos, and powerful harmonica playing.

Address: 700 S Wabash Ave

29. Witness Thrilling Aerobatic Performances At Chicago Air And Water Show

The Chicago Air and Water Show is an annual event that showcases thrilling aerobatic performances by some of the best pilots in the world. Held on the shores of Lake Michigan, this two-day event attracts millions of spectators who come to witness the incredible displays of skill and precision.

One of the show's highlights is the performance by the U.S. Navy Blue Angels, the renowned flight demonstration squadron. With their signature blue and gold jets, the Blue Angels perform breathtaking maneuvers that include high-speed passes, tight formations, and incredible aerial acrobatics.

30. Attend The Chicago Jazz Festival

There is a lot of stuff to do Chicago for music lovers. The Chicago Jazz Festival is an annual music festival and one of the longest-running and most prestigious jazz festivals in the world. The festival showcases a wide variety of jazz styles, from traditional to contemporary.

The festival spans multiple days and stages, offering a diverse lineup of performances. It features performances by renowned jazz artists, including both established musicians and up-and-coming talents.

31. Indulge In Italian Cuisine At Little Italy

Little Italy in Chicago is a neighborhood known for its vibrant Italian culture and cuisine. Visitors can expect to find various authentic Italian eateries and rooftop restaurants that serve traditional dishes from different regions of Italy.

In addition to pizza and pasta, Little Italy offers a variety of other Italian specialties. Visitors can enjoy dishes such as osso buco, a braised veal shank served with risotto, or polenta, a cornmeal dish often served with meat or cheese.

32. Explore The Museum Of Broadcast Communications

The Museum of Broadcast Communications (MBC) is dedicated to preserving and showcasing the history of radio and television broadcasting. It features a collection of artifacts, including vintage radios, television sets, and broadcasting equipment.

It also houses a vast archive of audio and video recordings, photographs, and documents related to the history of broadcasting. Exhibits at the MBC cover a wide range of topics, such as the evolution of radio and television technology and the development of iconic shows.

Address: 360 N State St

33. Take A Free Guided Tour With Chicago Greeter

The Chicago Greeter is a great way for visitors to explore the city, learn about its unique character, and connect with locals who are passionate about sharing their knowledge and love for Chicago. Greeters are knowledgeable about Chicago's history, culture, architecture, and local attractions.

It offers a more personal and authentic experience compared to traditional guided tours, allowing visitors to discover hidden gems and gain a deeper understanding of the city's culture and history.

34. Get Amused At The Chicago Magic Lounge

The Chicago Magic Lounge is dedicated to the art of magic and offers a unique and intimate experience for guests. The lounge features a variety of magic shows, including close-up magic, stage magic, and interactive performances.

Guests can enjoy drinks and food while being entertained by professional magicians. The lounge also offers classes and workshops for those learning magic tricks.

Address: 5050 N Clark St

35. Enjoy Interactive Exhibits At Chicago Children's Museum

The Chicago Children's Museum is a non-profit organization that provides educational and engaging experiences for children and families. It features a wide range of exhibits and activities designed to promote learning through play.

Some exhibits include a construction zone where children can build and create, a water play area, a pretend supermarket, a dinosaur expedition, and much more. There is also a play area specifically designed for children under 5 years old.

Address: 700 E Grand Ave

36. Shop For Unique Finds At Maxwell Street Market

Maxwell Street Market is a historic open-air market with diverse food vendors and a variety of merchandise for sale. Visitors can find a wide range of products, including fresh produce, clothing, electronics, antiques, and much more.

The market is particularly famous for its food offerings, with numerous food stalls serving up delicious street food from various cultures, such as Mexican, Polish, African, and Caribbean cuisine.

Address: 800 S Desplaines St

37. Discover The City's Culinary Scene With Chicago Food Planet Tours

Chicago Food Planet Tours offers guided food tours designed to showcase the city's diverse culinary scene and highlight local food establishments. Participants can sample a variety of dishes from different cuisines while learning about the history and culture of the neighborhoods they visit. 

Some popular tours offered by Chicago Food Planet Tours include the "Best in Chow: Chicago River North" tour, the "Near North Food Tasting & Cultural Walking Tour," and the "Bucktown/Wicker Park Food Tour."

38. Explore The Trendy Bucktown

Bucktown is a trendy artistic neighborhood with a thriving art scene, culture, nightlife, green spaces, shopping, and more. The neighborhood is known for its fashion-forward offerings, with many local designers and independent retailers setting up shop here.

It boasts a wide range of trendy restaurants, bars, and cafes. The neighborhood also offers a vibrant nightlife scene, with trendy bars and clubs that attract a young and stylish crowd.

39. Explore The Vibrant Street Art In Pilsen Neighborhood

Pilsen is known for its vibrant arts scene, Mexican heritage, and historic architecture. Pilsen has a rich history, with many of its residents being of Mexican descent. This is reflected in the neighborhood's colorful murals, Mexican restaurants, and cultural events.

Walking through the streets of Pilsen, you'll find colorful murals adorning the sides of buildings, alleyways, and even entire blocks. These murals often depict themes of identity, immigration, social justice, and cultural pride.

40. Learn About History At DuSable Museum of African American History

DuSable Museum of African-American History is one of the oldest African-American museums in the country. The collection includes over 15,000 artifacts, including artwork, historical documents, photographs, and personal belongings of prominent African-American figures.

The exhibits cover various aspects of African American history, including slavery, the Civil Rights Movement, music, literature, and visual arts. It also hosts educational programs, lectures, workshops, and community events.

Address: 740 E 56th Pl

41. Experience The Vibrant Culture At Chinatown

One of the first things that you will notice when you visit Chinatown is the lively atmosphere. The streets are filled with colorful decorations, traditional Chinese music playing in the background, and the aroma of delicious Chinese cuisine wafting through the air.

The vibrant energy of the community is contagious and you can't help but feel a sense of excitement and liveliness. There are numerous restaurants, bakeries, and food stalls where you can indulge in traditional dishes like dim sum, Peking duck, and hot pot.

42. Attend A Classical Music Concert At Symphony Center

The Symphony Center is a renowned venue for classical music concerts. Located in the heart of downtown Chicago, it is home to the Chicago Symphony Orchestra (CSO).

This elegant venue features excellent acoustics and a seating capacity of over 2,500. The stage is spacious, allowing for large orchestras and choirs to perform. The beautiful architecture and décor of Orchestra Hall add to the overall experience of attending a classical music concert.

Address: 220 S Michigan Ave

43. Catch A Live Broadway Show

There are tons of things to do Chicago Illinois and one of them is attending a live Broadway show. The city has a rich history of hosting Broadway shows and is home to numerous theaters that regularly showcase productions from the Great White Way.

One of the most iconic Broadway theaters in Chicago is the Cadillac Palace Theatre, which has been hosting Broadway shows since 1999. This historic venue attracts top-notch productions and is known for its grand architecture and luxurious interiors.

44. Check Out Views From 360 Chicago Observation Deck

The 360 Chicago Observation Deck is a popular tourist attraction located on the 94th floor of the John Hancock Building. It offers breathtaking panoramic views of the city and Lake Michigan.

Visitors can experience the TILT, a unique feature that tilts guests outward at a 30-degree angle from the building's windows. This provides an adrenaline-pumping perspective of the city from 1,000 feet above the ground.

Address: 875 N Michigan Ave

45. Immerse In The History And Sounds At Johnny Twist Blues Museum

Johnny Twist Blues Museum is a dedicated museum that showcases the life and achievements of Johnny Twist, a renowned blues musician. The museum features a collection of artifacts, including personal belongings, instruments, and memorabilia that belonged to Johnny Twist.

Visitors can explore his early life, influences, and journey to becoming a celebrated blues musician. The Johnny Twist Blues Museum also offers interactive exhibits where visitors can listen to Johnny Twist's music, watch live performances, and learn about the evolution of blues music.

Address: 6455 S Cottage Grove Ave

46. Explore Art And Culture At National Museum Of Mexican Art

The National Museum of Mexican Art is dedicated to showcasing Mexican art and culture. It houses over 10,000 artworks, including paintings, sculptures, textiles, ceramics, and folk art. The collection spans from ancient Mexican artifacts to contemporary works by Mexican and Mexican-American artists.

The museum's building itself is a work of art, with vibrant murals and beautiful architecture that reflects Mexican artistic traditions. It regularly hosts exhibitions that explore various aspects of Mexican culture, history, and identity. 

Address: 1852 W 19th St

47. Escape To The Beautiful Chicago Botanic Garden

The Chicago Botanic Garden is a 385-acre living plant museum in Glencoe, Illinois, just outside Chicago. The garden features various plant displays and collections, including 27 display gardens and four natural areas. 

These gardens showcase different types of plants, such as roses, bonsai, water lilies, and prairie plants. The natural areas include woodlands, wetlands, and prairies that provide habitats for native plants and wildlife.

Address: 1000 Lake Cook Rd, Glencoe

48. Relax In The Green Spaces At Grant Park

Grant Park is a large urban park that covers an area of 319 acres. It is bordered by Lake Michigan to the east, Michigan Avenue to the west, Roosevelt Road to the south, and Randolph Street to the north. 

It is home to several notable landmarks and attractions, such as Buckingham Fountain, Millennium Park, and the Art Institute of Chicago. The park is also a popular venue for events and festivals, including the Taste of Chicago Food Festival and the Grant Park Music Festival.

49. Take A Guided Tour Of Frank Lloyd Wright Home and Studio

The Frank Lloyd Wright Home and Studio was the residence and workplace of renowned architect Frank Lloyd Wright from 1889 to 1909. The home and studio were designed by Wright himself, and they showcase his innovative architectural style and design principles.

The building features many of the characteristics that would become synonymous with Wright's work, such as open floor plans, natural materials, and integration with the surrounding landscape.

Address: 951 Chicago Ave, Oak Park

50. Enjoy Recreational Activities At Maggie Daley Park

Maggie Daley Park is a public park that spans over 20 acres. It features a large playground area called the Play Garden, which includes a climbing wall, slides, and a suspension bridge.

There is also a skating ribbon, which is a winding ice skating path that can be used in the winter months. Other attractions include a mini golf course, a rock climbing wall, and a tennis court. Spending an afternoon here is one of the best things to do in Chicagoland.

Address: 337 E Randolph St