10 Niche Things to do in Chicago to Appreciate the Windy City

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10 Niche Things to do in ChicagoRaymond Boyd - Getty Images

If the first thing you think of when you hear the word "Chicago" is the famous Bean sculpture (which is actually named Cloud Gate, FYI) or deep-dish pizza, I have news for you. The Midwestern locale—nicknamed The Windy City for what some people say refers to its breezy weather—is filled with tons of niche museums, wacky eateries, cultural attractions, and more spots that are as fun as they are unique.

For example, if you're a Wizard of Oz fan, check out the Oz-themed park, whereas if you're into architecture, Graceland Cemetery and its memorials designed by famous local architects is the way to go—and this is just the tip of the iceberg. Scroll ahead for some quirky must-visit spots.

Frank Lloyd Wright Robie House

If you're a Frank Lloyd Wright enthusiast, you have to head over to the Robie House in Chicago's Hyde Park neighborhood. The Prairie-style home was completed in 1910 and is a U.S. National Historic Landmark.

interior, frank lloyd wright robie house, chicago, illinois
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Oz Park

This magical park, created in honor of The Wizard of Oz author L. Frank Baum, is a must-visit for fans of the book and movie. Located in Chicago's Lincoln Park neighborhood, you can enjoy its "Emerald Garden" with beautiful flowers, "Dorothy's Playlot" filled with playground equipment, and the charming statues of the Tin Man, Scarecrow, and more dotted throughout.

tin man statue at oz park, chicago, illinois
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The Fountain of Time

Installed over a hundred years ago in Chicago's Washington Park, this statue, made from hollow-cast concrete and reinforced with steel, is considered one of the city's most important historic artworks. Renowned artist Lorado Taft sculpted it, and it took over a decade to finish.

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Palmer House Hilton Hotel

This isn't just any old luxury hotel—this is the hotel that invented the chocolate brownie. As the story goes, the delicious treat was dreamed up in the Palmer House Kitchen during the late 1800s. The recipe is served at the hotel today and is still a huge hit.

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American Writers Museum

Whether you're an aspiring writer or a published author, you'll appreciate the American Writers Museum, an interactive museum celebrating American writing. Here, you'll find fascinating permanent exhibitions, temporary gallery installations, and a calendar of literary-related events for all ages.

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Graceland Cemetery

Nope, this Graceland isn't in Tennessee but in Chicago. Graceland Cemetery is another one of the city's hidden gems, nestled in its Uptown neighborhood. It has a park-like feel and dates back to the 1860s, when a prominent local lawyer, Thomas Bryan, purchased the cemetery's original 80 acres. It's also famously known as the "Cemetery of Architects," boasting many memorials and monuments designed by famous Chicago architects.

famous graves, crypts, mausoleums and headstones in chicago
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Dusty Groove

Get your music fix at Dusty Groove, one of the city's (and country's) most loved record shops—in 2010, Rolling Stone named Dusty Groove as the #3 record store in the country. Interestingly enough, Dusty Groove started as an internet business in 1995, later moving to a storefront after it took off.

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How fun are the 12-foot dancing hot dog statues on the top of Superdawg? No visit to Chicago is complete without grabbing a Superdawg dressed with mustard and piled high with tangy piccalilli, kosher dill pickles, chopped Spanish onions, and hot peppers. The talked-about drive-in opened in 1948 and is a Windy City staple.

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Green Mill Cocktail Lounge

Movie buffs may immediately recognize this picture of Green Mill Cocktail Lounge in downtown Chicago—films such as High Fidelity, The Lake House, and others shot scenes here. The jazz club has been around for decades and has hosted big names such as Louis Armstrong and Billie Holliday.

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Former Home of Al Capone

If mob history is your thing, head over to the former home of Al Capone, where you can get a glimpse of how the infamous mobster lived in the 1920s. Capone bought the multi-family Prairie Avenue pad for $5,000 and lived in it with his wife, mother, son, and sisters while his brothers took the additional units. According to real estate records, the property most recently sold in 2019 for $226,000.

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