What is the best walking tour Chicago for architecture?

While there are many options, this Gold Coast route is ideal for seeing the transition from Gilded Age styles to modernism. It includes key sites like the Driehaus Museum and the Sullivan-designed Charnley-Persky House.

Can you go inside the mansions on the Gold Coast?

The Driehaus Museum and the Newberry Library are open to the public during specific hours. Most other mansions, including the original Playboy Mansion, are now private residences and can only be viewed from the exterior.

Where is the original Playboy Mansion in Chicago?

The original Playboy Mansion is located at 1340 North State Parkway. It served as Hugh Hefner's home and the company headquarters from 1959 until the mid-1970s.

Is the Gold Coast neighborhood safe for walking?

Yes, the Gold Coast is one of the safest and most affluent residential neighborhoods in Chicago. It is well-lit and very walkable, making it perfect for an independent neighborhood stroll.

Is this walking route accessible for strollers or wheelchairs?

Yes, the entire route follows standard city sidewalks with curb cuts at every intersection. The terrain is flat, making it accessible for strollers and wheelchair users.

What is the history of Washington Square Park in Chicago?

Established in 1842, it is Chicago's oldest small park. It became famous as 'Bughouse Square,' a public forum for soapbox orators and free speech debates during the early 20th century.

When is the best time to explore the Gold Coast?

Morning or early afternoon is best for architectural photography, as the sun illuminates the eastern-facing facades. Weekdays are generally quieter than weekends.

Are there public restrooms along the Gold Coast walking route?

Public restrooms can be found inside the Newberry Library during their business hours. Otherwise, you may need to visit a cafe or restaurant on nearby State Street.

What architectural styles are found on Astor Street?

North Astor Street features a diverse mix of styles, including Richardsonian Romanesque, Queen Anne, Georgian Revival, Art Deco, and French Renaissance Revival.

Zigway - The Guide Follows You

About This Tour

Step into the world of Gilded Age opulence on this self-guided walk through Chicago's most prestigious neighborhood. Following the Great Chicago Fire of 1871, the city’s elite abandoned the South Side and transformed the swampy shoreline of Lake Michigan into a bastion of wealth known as the Gold Coast. This walking route invites you to explore the architectural masterpieces that defined an era of unprecedented prosperity and social ambition. As you stroll through these quiet, tree-lined streets, you will encounter the heavy stone facades of Richardsonian Romanesque mansions and the sleek, early modernist lines that would eventually revolutionize American architecture. This neighborhood stroll is not just about the bricks and mortar; it is about the titans of industry who built them—from bankers and publishers to the king of the Playboy empire. You will see the Richard H. Driehaus Museum, often called Chicago’s 'Marble Palace,' and the Newberry Library, a world-class research institution that overlooks the historic 'Bughouse Square.' The route also highlights the Charnley-Persky House, a critical collaboration between Louis Sullivan and Frank Lloyd Wright that signaled the birth of modern architecture. This walking tour Chicago experience offers a rare glimpse into the private world of the 19th-century elite, away from the hustle of the Loop. Whether you are an architecture enthusiast or a photography lover, this self-guided adventure provides the freedom to linger at your own pace. You can marvel at the intricate ironwork of North Astor Street or imagine the legendary parties at the original Playboy Mansion. This walking route is a perfect way to experience the layer of history that makes Chicago one of the world's great architectural capitals. Discover how the city's leaders rebuilt from the ashes to create a district of enduring beauty and influence on this comprehensive neighborhood stroll.

Highlights

The Richard H. Driehaus Museum, known as the 'Marble Palace'

The historic Newberry Library and its storied research collections

Washington Square Park, the city's oldest small park and former 'Bughouse Square'

The original Playboy Mansion, former home of Hugh Hefner

The Charnley-Persky House, a masterpiece by Sullivan and Wright

The Landmark District of North Astor Street

Tour Stops (6)

The Richard H. Driehaus Museum

Begin your self-guided adventure at the Samuel M. Nickerson House, now the Richard H. Driehaus Museum. Completed in 1883, this mansion was once the most expensive private residence in Chicago, earning the nickname 'The Marble Palace.' Nickerson, a wealthy banker, spared no expense, commissioning an interior filled with seventeen different types of marble, rare woods, and stained glass. The building is a premier example of the Richardsonian Romanesque style, characterized by its heavy, rusticated stone exterior and rounded arches. It stands as a testament to the wealth that flooded into Chicago during the late 19th century. Take a moment to admire the intricate carvings on the exterior before you continue your neighborhood stroll.

Washington Square Park

A short walk north brings you to Washington Square Park, Chicago's oldest small park, established in 1842. While it appears peaceful today, this area earned the nickname 'Bughouse Square' in the early 20th century. It became a legendary site for soapbox orators, poets, and political radicals who gathered here to debate everything from anarchy to religion. It was a center of free speech where anyone with a message could find an audience. The park is surrounded by historic architecture, providing a green oasis in the heart of the Gold Coast. Imagine the lively atmosphere of the past as you enjoy the shade of the mature trees that line the perimeter.

Newberry Library

Overlooking the park is the Newberry Library, an independent research library founded in 1887. The building itself is a work of art, designed by Henry Ives Cobb in the Spanish Romanesque style. Its heavy granite walls and rhythmic arches house millions of books, maps, and manuscripts focused on the humanities. The Newberry is world-renowned for its collections on genealogy, American history, and the history of printing. It serves as a quiet sanctuary for scholars and the public alike. Note the symmetry and the grand entrance, which reflect the civic pride of Chicago’s leaders as they sought to establish the city as a cultural peer to East Coast giants like New York and Boston.

Original Playboy Mansion

Continue north to 1340 North State Parkway, the original Playboy Mansion. This 70-room French Brick and limestone residence was built in 1899 for Dr. George Swift Isham. However, it gained international fame when Hugh Hefner purchased it in 1959. During the 1960s and 70s, it was the center of the Playboy empire, famous for its lavish parties and the underwater window in the basement swimming pool. A brass plate on the door once famously read, 'Si non oscillas, noli tintinnare,' which translates to 'If you don't swing, don't ring.' Today, the building has been converted into luxury condominiums, but its legacy as a symbol of the mid-century sexual revolution remains a fascinating chapter in Gold Coast history.

Charnley-Persky House Museum

At the corner of Astor and Schiller, you will find the Charnley-Persky House. This building is a pivotal landmark in architectural history, completed in 1892. It was designed by Louis Sullivan with the assistance of his then-draftsman, Frank Lloyd Wright. At a time when most mansions were covered in ornate Victorian decoration, this house was shockingly modern. Its simple, geometric forms and emphasis on horizontal lines signaled a break from European traditions and the beginning of a uniquely American style of architecture. The house is now the headquarters of the Society of Architectural Historians and remains one of the most significant residential buildings in the United States.

North Astor Street

Conclude your walk along North Astor Street, the heart of the Gold Coast Historic District. This street is named after John Jacob Astor, though he never lived in Chicago; the name was chosen to lend an air of New York prestige to the area. As you walk, you will see an incredible variety of architectural styles, including Queen Anne, Tudor Revival, and Art Deco. Each house tells a story of the family that commissioned it, showcasing the diverse tastes of Chicago’s elite. From the Patterson-McCormick Mansion to the smaller, elegant row houses, this street remains one of the most expensive and well-preserved residential corridors in the country. It is the perfect place to capture a final few photos of Chicago’s Gilded Age splendor.

Frequently Asked Questions

This self-guided walk typically takes between 60 and 90 minutes. The total distance is roughly 1.5 miles, allowing plenty of time for photography and admiring the historic mansions along Astor Street.