Non-Touristy Experiences in Chicago

Marvel at Chicagos architecture during your stay near Millennium Park
Marvel at Chicago's architecture during your stay near Millennium Park | Courtesy of Renaissance Chicago Downtown Hotel

Tired of craning your neck to look up at skyscrapers? Seen enough pictures of “The Bean” to last a lifetime? Fed up of crowds of tourists getting in your way in every museum? Fear not—there’s plenty of quieter, cooler and weirder options in Chicago, from bars and theaters loved by locals to unusual shops and museums and abusive hot dog stands. Here are the best gems you won’t find in your guide book.

Music Box Theatre

This old picture house dates back to 1929 and still has its original architecture and design. Known for its independent and foreign films, it also holds special events from the Chicago Film Society and the Chicago Critics Film Festival. Look out for “Whitey,” the manager of the Music Box Theatre from its opening night until 1977 when he fell asleep on the couch in the lobby and never woke up—he can still be felt pacing Aisle 4.

Graceland Cemetery

Described as “An Oasis of Art, Architecture, and Landscape Design,” this large cemetery in Uptown is the final resting place of many of Chicago’s greatest citizens. Notable burials include a number of architects who shaped the city’s skyline, including Daniel H. Burnham, Ludwig Mies van der Rohe, and Bruce Graham, as well as Graham’s colleague on the Willis Tower and the John Hancock Center, engineer Fazlur Khan. It is also the burial place of many recognizable politicians, athletes, and industrialists.

Oz Park

While The Wizard of Oz is not widely associated with Chicago, author L. Frank Baum lived in the Lincoln Park area in the 1890s, and Chicago’s George M. Hill Company first published The Wonderful Wizard of Oz in 1900. This small neighborhood park near his home was named in his honor in 1976 and features statues of the Tin Man, Cowardly Lion, Scarecrow plus Dorothy and Toto by sculptor John Kearney.

International Museum of Surgical Science

Housed in a 1917 mansion in the Gold Coast neighborhood is the International Museum of Surgical Science, North America’s only museum devoted to surgery. It details the history of surgery throughout humanity with its permanent collection of art and artifacts and medically themed exhibitions and programs. It also has a contemporary art exhibition program featuring work around medicine and the body, and a library featuring over 1,000 rare texts.

Leather Archives & Museum

The Leather Archives & Museum in Rogers Park has dedicated itself to the preservation of leather, kink, and fetish lifestyles since Chuck Renslow founded it in 1991 to house the artworks of his late partner. Today, the collection contains erotic art, historical sadomasochism devices, and papers and records from notable activists, artists, organizations, and much more. The library is available for research purposes.

Talks at the Seminary Co-op

One of the city’s best bookstores on the campus of the University of Chicago, the Seminary Co-op hosts regular talks, readings and events at its locations on S. Woodlawn Avenue and 57th Street, featuring the best and brightest writers and academics from across the globe. Among the store’s 50,000 members is President Obama, who would shop there frequently with his wife and children before he became president.

Woolly Mammoth Antiques and Oddities

Looking for a unique or weird present that’s probably related to death or just an unusual shopping experience? Andersonville’s Woolly Mammoth Antiques and Oddities specializes in vintage and antique taxidermy and medical paraphernalia among its large range of miscellaneous curiosities. Owners Adam and Skye Rust had the idea for the store after inheriting a set of teeth, and told Time Out Chicago: “We stock these things for a selfish reason: to make ourselves more comfortable with dying.”

The Wieners Circle

Ever since the early ‘90s when owner Larry Gold reprimanded an unattentive customer with some choice language, the late-night drunk crowd from nearby Lake View and Lincoln Park have flocked to this hot dog stand to trade barbs with the famously sassy and surly staff. Not for everyone, the comments are often personal, and the mood can quickly move from playful to aggressive. Even the elite can’t escape the sass—2016 saw the launch of a three-inch hot dog called the “Trump footlong.”

Busy Beaver Button Museum

Alongside a shop making and selling custom buttons for over 20 years, the Busy Beaver Button Co. also has one of the world’s only museums dedicated to the history of pinback buttons. The collection has examples from throughout the 20th century, dating back to when pinback buttons were patented in 1896, covering political campaigns, causes, advertising, sports, music, and humor. Be sure to donate any old buttons you may have.

Get on your bike

Tired of the city as a whole? Grab your bike, or rent one from a Divvy station, and head out into the suburbs where there are many great cycling trails to find. The Lakefront Trail is pretty touristy but leads to quieter areas like the North Sheridan Road, while the north branch of the Chicago River and the Des Plaines River to the south see quiet green areas with many miles of trails.

Did you know – Culture Trip now does bookable, small-group trips? Pick from authentic, immersive Epic Trips, compact and action-packed Mini Trips and sparkling, expansive Sailing Trips.

Culture Trips launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes places and communities so special.

Our immersive trips, led by Local Insiders, are once-in-a-lifetime experiences and an invitation to travel the world with like-minded explorers. Our Travel Experts are on hand to help you make perfect memories. All our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.

All our travel guides are curated by the Culture Trip team working in tandem with local experts. From unique experiences to essential tips on how to make the most of your future travels, we’ve got you covered.

close-ad
Edit article