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.
Music Box Theatre, 3733 N Southport Ave, Chicago, IL, USA, +1 773 871 6604
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.
Leather Archives & Museum, 6418 N Greenview Ave, Chicago, IL, USA, +1 773 761 9200
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.
Seminary Co-op, 5751 S Woodlawn Ave, Chicago, IL, USA, +1 773 752 4381
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.”
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.”
The Wieners Circle, 2622 N Clark St, Chicago, IL, USA, +1 773 477 7444
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.
Busy Beaver Button Museum, 3407 W Armitage Ave, Chicago, IL, USA, +1 773 645 3359
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.