One of America’s biggest, boldest cities, Chicago has a long history of doing its own thing. From deciding that pizza should be as thick as lasagna and that hotdogs aren’t complete without a dash of celery salt, to building the world’s first ever skyscraper back in 1884, Chicagoans play by their own rules. It’s the city’s distinct individuality that makes it an ideal hipster hangout.
If you’re heading to Chi-town, but want to skip the tourist path, check out the following guide to the city’s hippest local hangouts:
Ranked number 4 on Forbes’ list of America’s “Hippest Hipster Neighbourhoods”, Chicago’s Wicker Park is labelled the “Midwest Mecca of hipsterdom”. Wicker Park has long been associated with Chicago’s brewery industry. The neighbourhood’s local, independent Pipeworks Brewing Company was voted ‘Best New Brewery’ in 2012 by RateBeer.com, and most area bars are fully stocked with its delectable microbrews. Wicker Park is also a well-known artists community, with several galleries, offbeat shops and music venues lining its historic streets. The Lloyd Dobler Gallery is particularly brilliant at showcasing unique artwork from emerging local artists. During your visit to Wicker Park, also be sure to check out the grand Victorian-era mansions that once housed the area’s wealthiest residents. The old buildings add to the neighbourhood’s unique mix of culture, history and artistic flare.
Plenty of dive bars, bookstores and music venues, Logan Square, particularly its Bucktown neighbourhood, is a hipster haven. Situated in northwest Chicago, both Bucktown and the rest of Logan Square have more than enough unique ways to fill your time. Independent coffee shop Café Mustache (you asked for hipster, you got it!) in Logan Square and Danny’s bar in Bucktown are equally funky settings to enough a brew, whether you favour the caffeinated or alcoholic variety. This area is also home to many quirky boutiques. Comic-book fans will love Challenger’s Comics on Western Ave and, if you’re a film buff, head over to eclectic video shop Odd Obsession on Milwaukee Ave.
While influenced by its Irish, German and Czech roots (‘Pilsen’ is also a town in western Bohemia), this Chicago neighbourhood is now home to a large Mexican-American community. It’s characterised by its artistic influence and a thriving independent theatre scene. From vibrant murals that adorn the sides of brick buildings to the brilliant Museum of Mexican Art, Pilsen is one of the best places in the country for Mexican-American artwork. If you happen to be in Pilsen on the second Friday of the month, you’re in for quite the treat an event known as the Pilsen Art Walk. During the event, the neighbourhood’s many art galleries along 18th and 19th Streets, between Halsted and Peoria, open their doors to the public and serve free wine and snacks to interested art lovers.
In addition to fine art, Pilsen is also known for its edgier performance art scene, with the Dream Theatre and the EP Theatre both ideal places to watch the work of modern playwrights. So, while Chicago’s most popular tourist attractions are that way for a reason, there’s also plenty to explore off the traditional sightseeing path. Most of the flights from the UK to Chicago are usually around 8 hours, so you’ll have plenty of time to plan your visit around these local hotspots. Just remember, leave some room for a bit of spontaneity. The shops, bars, parks and museums that you stumble across by accident are often the best, most memorable parts of your visit.