Wicker Park has earned a reputation for its delicious food, trendy cocktail lounges, craft breweries, and nightlife. But you’ll still find some of the best dive bars, where drinks are affordable, the regulars know the bartenders by name and nobody cares what you’re wearing.
While Wicker Park has changed over the years, these neighborhood institutions have managed to hold onto the spirit that made the area famous long before it became one of Chicago’s trendiest spots. Whether you're celebrating a bachelorette party, bonding with coworkers, or just looking for cheap drinks and live music, these are the Wicker Park dive bars packed with local history and genuine Chicago personality.
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When people ask us where to start a dive bar crawl in Wicker Park, Gold Star Bar is always our first recommendation. Located on Division Street, Gold Star has been serving drinks to neighborhood residents for decades. Walk inside and you’ll immediately understand the appeal. The crowd is diverse, spanning multiple generations of Chicagoans, longtime regulars, service industry workers and curious visitors.
You'll find nothing too fancy here. Instead you'll find:
Visit Gold Star Bar: 1755 W Division St, Chicago, IL 60622
Opened in 1954, Phyllis’s has long been considered one of Wicker Park’s most beloved institutions. The bar famously describes itself as “the only place in Wicker Park that hasn’t changed since 1954.” The colorful murals and intimate stage have made it a place where musicians, artists and regulars have gathered for affordable drinks and live music.
For visitors looking for an authentic piece of Chicago nightlife, you’ll find:
Visit Phyllis’ Musical Inn: 1800 W Division St, Chicago, IL 60622
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Black Hole Bar has become a favorite among locals looking for a relaxed atmosphere with neighborhood dive bar charm. While it offers a large selection of craft beer and whiskey, the dimly lit interior, decor and friendly crowd make it easy to stay awhile.
Unlike many of the typical popular spots in Chicago, at Black Hole Bar you’ll find:
Visit Black Hole Bar: 1942 W Division St, Chicago, IL 60622
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Sometimes the best bars are the simplest ones. The Corner Bar has built its reputation by focusing on what matters most: affordable drinks, friendly service and a fun place to gather with friends.
Tucked away from busier spots, you’ll find:
Visit The Corner Bar: 2224 N Leavitt St, Chicago, IL 60647
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Few places capture the spirit of Chicago’s dive bar culture like Lemming’s Tavern. This bar has earned a loyal following for its laid-back atmosphere, affordable drinks and personality. The interior embraces the worn-in charm that defines many of Chicago’s best dive bars.
Inside this neighborhood fixture, you’ll find:
Visit Lemming's Tavern: 1850 N Damen Ave, Chicago, IL 60647
Whether you’re grabbing a cheap beer at Gold Star, catching live music at Phyllis’ Musical Inn, enjoying whiskey at Black Hole Bar, stopping into The Corner Bar or chatting with locals at Lemming’s Tavern, these neighborhood institutions offer a glimpse into the Chicago that locals love.
And in a city filled with rooftop bars, cocktail lounges and trendy restaurants sometimes the most memorable night out still starts with a dive bar.
If you love the historic vibe of Wicker Park’s dive bars but want to explore another side of Chicago nightlife, head about 10 minutes south to the West Loop.
Our Gateway to the West Loop Food Tour introduces you to one of Chicago’s coolest neighborhoods, where more hidden-gem taverns, neighborhood bars and culinary institutions exist alongside some of the city’s most acclaimed restaurants.
Ready to discover even more of Chicago? Browse our tour calendar to experience other food tours in Chicago that showcase the city’s best food, history and architecture with expert local guides.
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