Hipster Hopping: The 3 Coolest Neighborhoods in Chicago

Sure, Chicago’s downtown is great, but to truly experience the city like a local you need to get out into one of its 77 diverse neighborhoods. And if you want to be like one of the cool kids, you need to go where the cool kids go.

Here, we break down three of the trendiest neighborhoods in the city by geographic area, along with picks for must-visit destinations within each ‘hood.

West Side: Logan Square

Swing a bag of artisanal craft beer hops in Logan Square and you’re bound to spill at least some of them into the beards of the many flannel-covered hipsters who call this neighborhood home.

Having replaced Wicker Park as the city’s most well-known epicenter of cool, today Logan Park has reached a critical mass of ever-evolving bars and restaurants along its main drag, Milwaukee Avenue — appropriately nicknamed the “Hipster Highway.”

But even if you don’t measure your net worth by the tightness of your jeans or the obscurity of your vinyl collection, there’s plenty to like here, including some of the finest chefs in America pushing the boundaries of contemporary cuisine at Michelin Bib Gourmand restaurants like Giant and Fat Rice.

And if you’re thirsty, you couldn’t have come to a better place. Take your pick of where to imbibe, from dives like Cole’s and Bob Inn to high-class temples of A-list mixology, including The Whistler and Scofflaw. For a music fix, swing by The Burlington to discuss the latest issue of Pitchfork as live local acts jam on a small stage.

For one of the best outdoor patios in Chicago (if not America), the original Parson’s Chicken & Fish dishes up standout chicken served with a side of Negroni slushies and pingpong on a hot summer day.

Follow your meal with some late-night dancing at Slippery Slope or the East Room and you pretty much have yourself the quintessential Logan Square experience. Your Instagram followers will be so totally jelly.

South Side: Bridgeport

While Pilsen has long been regarded as the “next cool neighborhood” in Chicago, the often-overlooked, working-class, South Side neighborhood of Bridgeport has slowly been trending cool in recent years.

The change is thanks in part to a series of new developments that includes the opening of one of Chicago’s best new breweries, Marz Community Brewing, a shimmering palace of cool that checks all the hipster boxes: a warehouse setting; top-of-the-line, locally produced craft beer; vintage arcade games; and eats like Cuban sandwiches and fried bologna.

The brewery is located just a five-minute drive from the neighborhood’s other chief outpost of cool, Maria’s Packaged Goods & Community Bar, operated by many of the same folks from Marz. Long known for having one of the largest beer lists in the city paired with ultra-cool DJ nights and eats at their in-house Korean/Polish street food emporium Kimski, Maria’s also enjoys a reputation as one of the few remaining “slashies” (half bar/half liquor store) still operating in the city.

When you’re tired of boozing, sober up with some fresh-brewed artisanal coffee from the original location of Bridgeport Coffee before making your way to Palmisano Park, a former quarry and landfill turned into a leafy, 27-acre park with trails and a fishing pond.

North Side: Andersonville

When most people think of Chicago’s North Side, they think of the bro culture that dominates the bars outside Wrigley Field. But a bit further north in the small neighborhood of Andersonville, corporate interchangeability gives way to a small strip of cafés and shops brimming with offbeat local charm and lively action along its main drag, Clark Street.

While traditionally recognized for its strong Swedish heritage, these days A-Ville is one of the city’s most diverse neighborhoods, offering everything from hipster-approved dive bars and LGBT-friendly establishments to quirky storefront theater spaces and authentic Middle Eastern eateries.

Most Andersonville explorations begin (or end) at one of its two main epicenters of cool: Hopleaf (one of the best beer bars in the city) and Simon’s Tavern (one of its finest dive bars).

From there, you can grab a burger with drag queens at Hamburger Mary’s, peruse feminist literature at the ripped-from-“Portlandia” Women & Children First bookstore, shop for obscure oddities like skulls and taxidermy at Woolly Mammoth, or indulge in the glorious local sport of turtle racing at Big Joe’s. See, we told you this place was unique.