20 Best Things to Do in Chicago

Chicago’s rich cultural history, combined with its unique offerings, makes it a top destination for travelers worldwide. The best things to do in Chicago offer a vibrant mix of artistic, historical, and modern experiences. In this guide, we will explore 20 of the most exciting activities and attractions to help you make the most of your visit to the Windy City.

See the List below For The 20 Best Things to Do in Chicago;

1. The Magnificent Mile

20 Best Things to Do in Chicago

The Magnificent Mile, fondly called ‘The Mag Mile’ by locals, is the heart of Chicago’s shopping and entertainment district. A bustling stretch of Michigan Avenue, it boasts high-end boutiques, department stores, and a plethora of dining options. But it isn’t just about shopping; The Mag Mile is home to some of Chicago’s most significant architectural wonders. As you stroll, you’re surrounded by a combination of historic and modern buildings. Taking the time to look up, you might notice the iconic John Hancock Center. This mix of retail therapy and architectural appreciation makes it one of the best things to do in Chicago for tourists and locals alike.

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2. Millennium Park & Cloud Gate (The Bean)

20 Best Things to Do in Chicago

Located in the heart of downtown, Millennium Park is an iconic symbol of Chicago. Home to the Cloud Gate, commonly known as ‘The Bean’, this stainless steel sculpture reflects the city’s skyline, providing a unique photo opportunity for visitors. Beyond The Bean, Millennium Park offers a myriad of art installations, walking paths, and seasonal events. During summer, locals and tourists flock to the Jay Pritzker Pavilion for free concerts. In winter, the McCormick Tribune Ice Rink is the place to be. Indeed, Millennium Park stands as a testament to Chicago’s commitment to art, community, and green spaces, making it one of the best things to do in Chicago.

3. Navy Pier

20 Best Things to Do in Chicago

An iconic landmark, Navy Pier is more than just a pier; it’s a world of entertainment. With a range of activities from the Centennial Wheel to the Chicago Shakespeare Theater, there’s something for everyone. Children can delve into interactive exhibits at the Chicago Children’s Museum, while adults can enjoy cruises offering breathtaking views of the skyline. As you meander through, the aroma of Chicago-style popcorn from Garrett Popcorn Shops might tempt you. With numerous events year-round, the Navy Pier encapsulates the vibrancy of the city, making it one of the best things to do in Chicago.

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4. Art Institute of Chicago

20 Best Things to Do in Chicago

The Art Institute of Chicago is not just a museum; it’s an experience. As one of the oldest and largest art museums in the US, it houses a collection that spans thousands of years. From ancient artifacts to modern art, from Seurat’s “A Sunday on La Grande Jatte” to Grant Wood’s “American Gothic”, the breadth of art here is astounding. Beyond the artworks, the building itself, designed in the Beaux-Arts architectural style, is a masterpiece. Visitors can easily spend a whole day exploring its vast corridors, making it one of the best things to do in Chicago for art enthusiasts.

5. Willis Tower Skydeck

20 Best Things to Do in Chicago

No visit to Chicago is complete without a trip to the Willis Tower Skydeck. Once the tallest building in the world, the Skydeck offers an unparalleled view of the city. Stepping onto ‘The Ledge’, a glass-floored balcony on the 103rd floor, gives thrill-seekers a unique perspective. On clear days, you can see four states! As the elevator ascends, you’re treated to a multimedia presentation about the city’s history and the tower’s significance in Chicago’s skyline. This combination of history, architecture, and sheer thrill makes it one of the best things to do in Chicago.

6. Chicago Riverwalk

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Nestled alongside the serene Chicago River, the Riverwalk offers a tranquil escape in the midst of the bustling city. Stretching for miles, this pedestrian-friendly path is a hub of activity. From boat rides showcasing the city’s architectural wonders to alfresco dining, there’s no shortage of experiences here. Historically, the river played a pivotal role in Chicago’s growth, and as you traverse its banks, the stories and legends associated with it come alive. Considering its blend of relaxation, history, and architecture, the Riverwalk easily ranks among the best things to do in Chicago.

7. Shedd Aquarium

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A deep dive into marine life awaits you at the Shedd Aquarium. Home to over 32,000 aquatic animals, this place is a marvel for ocean enthusiasts. The exhibits transport you from the Amazon Rainforest to the waters of the Pacific Northwest. The ‘Wild Reef’ exhibit, for instance, simulates a Philippine coral reef and is teeming with sharks, rays, and vibrant coral. Beyond just viewing, the aquarium offers interactive experiences, allowing visitors to touch certain species. The blend of education, conservation, and sheer wonderment it offers makes the Shedd Aquarium one of the best things to do in Chicago.

8. Field Museum

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Hadrosaur Skeleton, Field Museum” by Lisa Andres is licensed under CC BY 2.0

Delve into the realms of natural history at the Field Museum. With over 40 million artifacts and specimens, it’s a treasure trove of knowledge. The star attraction is undoubtedly ‘Sue’, the most extensive and best-preserved Tyrannosaurus rex ever found. But that’s just the tip of the iceberg. From ancient Egyptian tombs to the glittering gem exhibit, the museum captures the essence of our planet’s history and the evolution of its inhabitants. For those passionate about history, culture, and science, the Field Museum is undeniably one of the best things to do in Chicago.

9. Chicago Cultural Center

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Chicago Cultural Center GAR Dome HDR” by fusionpanda is licensed under CC BY-NC 2.0

Housed in a neo-classical building, the Chicago Cultural Center is both an architectural gem and a hub for the arts. Its interiors are adorned with intricate mosaics, marble, and two awe-inspiring stained-glass domes. But the beauty isn’t just skin deep. The center hosts an array of free public events, from music concerts to art exhibits. As a testament to Chicago’s commitment to culture and the arts, it provides a space where both residents and tourists can immerse themselves in creativity. Given its architectural and cultural significance, it’s among the best things to do in Chicago.

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10. Wrigley Field

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Baseball and Chicago go hand in hand, and at the heart of this love affair is Wrigley Field. This iconic stadium, home to the Chicago Cubs, has witnessed some of baseball’s most memorable moments. A visit here isn’t just about watching a game; it’s about immersing oneself in a rich sporting history. The vintage scoreboard, the ivy-covered outfield walls, and the passionate fans make it a unique experience. Whether you’re a baseball aficionado or someone keen on understanding American culture, a visit to Wrigley Field is undoubtedly one of the best things to do in Chicago.

11. Chicago Architecture River Cruise

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When it comes to appreciating Chicago’s iconic skyline, there’s no better perspective than from its waterways. The Architecture River Cruise offers a narrated journey through the city’s architectural marvels. As you sail, guides share stories of the visionaries who shaped the city. From the neo-gothic Tribune Tower to the ultramodern Aqua building, the cruise is a visual treat. Given its combination of information, leisure, and spectacular views, the cruise stands out as one of the best things to do in Chicago.

12. Lincoln Park Zoo

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Nestled in the heart of the city, Lincoln Park Zoo is a serene escape that connects visitors with nature. Home to a diverse range of species, this zoo emphasizes conservation and education. What makes it even more special is its free admission, ensuring that everyone has access to these wonders. Seasonal events, interactive exhibits, and the sheer joy of watching animals in meticulously designed habitats make it one of the best things to do in Chicago.

13. Chicago Symphony Orchestra

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For those with an ear for classical music, the Chicago Symphony Orchestra (CSO) offers an unmatched experience. Housed in the historic Orchestra Hall, CSO has been enthralling audiences with impeccable performances for over a century. With world-renowned musicians and conductors gracing its stage, every performance is a testament to the city’s rich musical legacy. Attending a concert here is not just about the music; it’s about being part of a timeless tradition, making it one of the best things to do in Chicago.

14. The Second City

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Second City – An Event Apart Chicago 2014 Speaker Dinner” by Jeffrey is licensed under CC BY-NC-ND 2.0

Laughter is universal, and at The Second City, it’s abundant. As the breeding ground for many legendary comedians, this comedy club offers a mix of sketch comedy, improv, and theater. Every show is a burst of creativity, ensuring that no two nights are the same. For those seeking a light-hearted evening filled with laughter, visiting The Second City is unquestionably one of the best things to do in Chicago.

15. The Museum of Science and Industry

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An ode to human ingenuity, the Museum of Science and Industry offers an immersive dive into the world of technology and innovation. From coal mines to U-505 submarines, from tornado simulators to Apollo 8 spacecraft, the exhibits span various scientific domains. Interactive installations ensure that learning is hands-on, making it a favorite among families. With its blend of education and entertainment, it stands out as one of the best things to do in Chicago.

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16. Garfield Park Conservatory

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An urban oasis, the Garfield Park Conservatory is a haven for plant lovers. Spread across acres, it’s one of the largest conservatories in the nation. It showcases an astounding variety of plant species from different climatic zones, housed in distinct sections like the Desert House or the Fern Room. The meticulously designed landscapes transport visitors to different parts of the world. With events, workshops, and exhibitions, it’s a living, breathing testament to nature’s splendor, making it one of the best things to do in Chicago.

17. Chicago History Museum

Delve deep into Chicago’s past at the Chicago History Museum. It’s a gateway to understanding the city’s transformation from a small settlement to the global metropolis it is today. Exhibits range from the Great Chicago Fire to the city’s sports legacies. Rare artifacts, photographs, and interactive displays make history come alive, ensuring that visitors of all ages leave with newfound knowledge. For history buffs and curious minds alike, this museum is undeniably among the best things to do in Chicago.

18. North Avenue Beach

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Chicago might be miles from the ocean, but its lakefront is a beach lover’s paradise. North Avenue Beach, in particular, is a summertime favorite. With its sandy shores, volleyball courts, and the picturesque Lake Michigan as a backdrop, it’s a hub of relaxation and activity. The nearby beach house, reminiscent of a ship, offers amenities and refreshments. Whether you’re sunbathing, playing beach sports, or simply taking in the views, this beach is one of the best things to do in Chicago during warm months.

19. Buckingham Fountain

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One of the largest fountains in the world, Buckingham Fountain is a centerpiece of Grant Park. Its magnificent design, inspired by the Latona Fountain at the Palace of Versailles, is a sight to behold. During summer evenings, the fountain comes alive with light and music shows. It serves as a gathering spot, a place of celebration, and a symbol of the city’s grandeur. The mix of artistry and sheer scale makes visiting Buckingham Fountain one of the best things to do in Chicago.

20. Chicago’s Magic Parlour

Step into a world of illusions and wonder at Chicago’s Magic Parlour. Hosted by the talented Dennis Watkins, this intimate magic show is a blend of classic tricks and storytelling. Set in the historic Palmer House Hilton, the setting is as enchanting as the magic itself. The close-up nature of the show ensures every audience member is part of the experience. For those seeking an evening of astonishment and elegance, this is undoubtedly one of the best things to do in Chicago.


From the bustling shores of Lake Michigan to the historic corridors of its museums, Chicago is a city of endless wonders and vibrant experiences. Whether you’re an art aficionado, a history enthusiast, or someone seeking leisure and laughter, Chicago offers a rich tapestry of attractions to explore.

Each corner of the city tells a tale, and every experience is a chapter in the grand narrative of what makes Chicago truly special. As we’ve journeyed through just a handful of the best things to do in Chicago, it’s evident that the city’s charm lies in its diversity, history, and the warmth of its spirit. Whether you’re visiting for the first time or rediscovering familiar haunts, Chicago promises memories that will last a lifetime.

Traveling isn’t just about places, it’s about experiences. I’m Sachin, curating unique tales of exploration at Voyage Roams. Journey with me!

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