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Living in Historic Neighborhoods in Chicago

Whether you’re a bit of a history buff or are looking to experience Chicago in its entirety, there are some historic hotspots that you don’t want to overlook. These better-known attractions like Holy Name Cathedral, Frank Lloyd Wright’s Robie House, and the Historic Water Tower are all go-to’s. However, beyond popular historic tourist attractions, living in the historic neighborhoods strewn throughout the city hold the key to appreciating the full picture of The Windy City’s past. 

While these neighborhoods often contain designated historic districts and landmarks, some stand out through their efforts to preserve pieces of history. These extra steps for conservation often include giving new purpose to historic buildings, celebrating the culture that shaped these areas, and paying homage to the past through art and music.

Below are three neighborhoods that exemplify these efforts. While they all have a rich history in common, each one has a distinct vibe. The beauty of historic districts in Chicago is that there is one for everyone!

Gold Coast – The Epitome of Luxury Living

This luxurious neighborhood that borders Lake Michigan’s scenic waters came to be shortly after The Great Chicago Fire in the 1800s. Some of Chicago’s most prominent people founded this section of the city and transformed the swampy land into Lake Shore Drive. By the 1980s, this area was the second most affluent in America—beat out only by Manhattan’s Upper East Side.

Today, Gold Coast draws a large crowd for its luxury cuisine, high-end shopping, picturesque streets, and sandy shorelines that live up to the neighborhood’s name. 

Who is the Gold Coast Perfect For? 

Those who crave high-end living and food lovers. Everything about this neighborhood, from the boutiques to the high-rise condos with views of Lake Michigan, ooze luxury. Additionally, the array of gourmet restaurants in the area that offer fresh and flavorful cuisine is a food lover’s dream.  

Places to Experience the History of the Gold Coast

Bush & Gerts Piano Company

If you want a peek at more than the architecturally stunning facades of some of the luxury apartment buildings in the area, we highly suggest the Bush Temple as no appointment is needed. This historic French Renaissance Revival building that once held Bush & Gerts Piano Company is now a luxury apartment complex with a lobby open to the public. In the lobby, you will find the perfect escape from the commotion of the city with a health food café, plush seating, and a large co-working table. 

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Astor Street

This area is home to some of the most famous architecture in the city, including The Historic Water Tower and houses by Frank Lloyd Wright. Want a glimpse of what homes were like in this prestigious neighborhood before the contemporary luxury apartments and condominium developments? Astor Street is the place to go. You will get an eyeful of expansive mansions with magnificent architecture along this street—some that span entire blocks! 

The Newberry Library

This library is a bookworm’s dream. Founded in 1887, The Newberry Library is a gateway to more than 600 years of human history with 1.6 million books, 600,000 maps, and 5 million manuscript pages. It is open to the public and located in Washington Square.

Uptown – The Summer Resort Town

Uptown put itself on the map in the early 1900s as a summer resort town with its name derived from the community’s commercial center, the Uptown Store. Beyond summer fun, this area also became known for its entertainment as it drew in headliners like Charlie Chaplin, Frank Sinatra, and Duke Ellington. 

Today, it has some of the most prominent theatre and entertainment districts in Chicago with historic venues like the Aragon Ballroom and the Riviera Theatre. Its vibrant culture, music scene, and stunning vintage architecture found everywhere from Uptown apartments to entertainment venues make it a hotspot for tourists and locals alike. 

Who is Uptown Perfect For? 

Those who love outings and exploring new venues. You will never be bored in Uptown with its selection of entertainment, beaches, trails, and eateries.

Living in historic districts in Chicago

Places to Experience the History of Uptown

Graceland Cemetery

While this certainly isn’t a hidden gem, it is a must-see. Graceland Cemetery was founded in 1860. Its 121 acres with winding paths, grandeur sculptures, and an arboretum is the final resting place of many notable Chicagoans that helped establish the city. This includes architects Louis Sullivan (Frank Lloyd Wright’s mentor) and Ludwig Mies van der Rohe.

Sheridan Park Historic District

Within Uptown is the Sheridan Park Historic District, which holds many old treasures whose historic status protects them from demolition. One of which spans three blocks on Dover Street and contains an array of historic family homes. Many of these buildings were designed in a Victorian style that gives them a likeness to picturesque dollhouses. 

Green Mill Cocktail Lounge

This venue is overflowing with vintage charm and history. Anyone who visited this place from 1907-1910 might know it by its former name, Pop Morse’s Roadhouse, but three years after its conception, it became the Green Mill. This jazz club that pays homage to the Moulin Rouge in Paris (Red Mill) was once one of Al Capone’s haunts—and you can still find his favorite booth located west of the short end of the bar. 

Pilsen – The Artist’s Haven

Cradled by the Chicago River, Pilsen is historically a gateway for immigrants. In the late 19th century, the area was predominately inhabited by Czech immigrants and was named after what is now the Czech Republic’s 4th largest city. Fast-forward to the 1980s. This area’s demographic dramatically shifted to where 95% of the people in Pilsen had some Mexican decent—80% of the population being first- or second-generation immigrants from Mexico.

Today, the area has become more diverse but is still predominately Latino, with their culture and history proudly showcased through the neighborhood. This area that is home to one of the largest art districts in the city offers authentic international cuisine, an abundance of creative venues, and a lively nightlife. 

More like this: Market Spotlight: Chicago Suburbs

Who is Pilsen Perfect For? 

Creatives and entrepreneurs. The abundance of galleries, one-of-a-kind shops, and art from all disciplines means that Pilsen is always buzzing with inspiration. This area also has quite a few co-working spaces perfect for those who don’t have a home office or prefer to work outside the home. 

Places to Experience the History of Pilsen

Street Art

You don’t have to go far to experience the exquisite street art and murals in Pilsen that reflect the area’s heritage. These can be easily spotted throughout the neighborhood with their captivating subject matter and bright colors. However, the largest concentration and variety is found along the train tracks on 16th Street. 

Thalia Hall

If you are going to explore this area, you don’t want to skip out on one of the most historic venues in all of Chicago, Thalia Hall. This restored Romanesque Revival style building established in 1892 hosts live shows and concerts. Under Thalia Hall’s roof, there is also Dusek’s Board & Beer and the Punch House. While in what was once the building’s former carriage house is live piano music at the Tack Room. 

National Museum of Mexican Art

To get a deeper understanding of this area’s culture, the National Museum of Mexican Art on W 19th St. is a must. This free-admission museum has a permanent collection of over 10,000 pieces of work in various mediums, from paintings to textiles. 


Chicago strives to preserve its history through restoration projects, as well as designated historic districts and landmarks. And while above are just a handful of neighborhoods that exemplify these efforts and proudly showcase the city’s history, they only skim the surface. The Windy City is brimming with history around every corner—and living in a historic neighborhood is truly the best way to experience it in its entirety. 

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