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Dotted with independent vintage boutiques, trendy restaurants, and small fair-trade coffee shops, Wicker Park/Bucktown is a mecca for young artsy types and alternative post-grads, evident in the fact that more artists call the area home than anywhere else in Chicago.
The area’s Flat Iron Arts Building houses more than fifty galleries that keep the city’s burgeoning artistic spirit alive and well, but creativity can be found even outside the galleries in the form of everyone from tattoo artists to glass blowers.
Though just a few short train stops northwest of the downtown Loop, the bohemian neighborhood can seem miles from the big city, especially at the myriad cafés and brunch spots, small galleries, crowded pizza joints, and independent shops that pepper the sidewalk on Milwaukee Avenue, and that are usually bustling with youthful young professionals and relaxed hipsters.
Somewhat surprisingly, the area isn’t all about vegan bakeries and hemp clothing, however – in fact, its namesake park is dotted with enough restored mansions, refined cocktail lounges, and classy fusion restaurants to keep the trendy types happy too.
Although Wicker Park/Bucktown tends to be laid back during the day, the district comes to life at night when partygoers both casual and dressed to impress flock to the clubs and upbeat bars on Division Street and further north along the Damen/Milwaukee/North Avenue intersection.
Music lovers should be sure to check out the annual Wicker Park Fest – usually held in late July or early August – which draws tens of thousands of revelers into the streets for two days of cutting-edge bands.
20s / 30s / 40s / 80s Music / Bar Food
Party Earth Review Dinner, daily specials, freshly brewed beer, sports, and DJs – Moonshine delivers it all under one roof. Except the dog-friendly patio – that’s outside ... more
1824 West Division Street
Chicago, IL 60622
20s / 30s / 40s / After Work / Bar / Beer
Party Earth Review A blend of microbrewery and pizzeria, Piece has helped revive the popularity of thin crust pizza in a deep dish city, all the while serving an extensive list of in-house craft beers ... more
1927 West North Avenue
Chicago, IL 60622
20s / ATM / Artsy / Blues / Cash Only
Party Earth Review Just a few steps from the lively Wicker Park intersection of North and Damen Avenues, a large black and red star shines over what looks like a former gas station – and that’s because ... more
1531 North Damen Avenue
Chicago, IL 60622
20s / 30s / 40s / Artists / Bands / Bar / DJ
Party Earth Review Situated inside the massive 88,000-square-foot Flat Iron Arts Building, Debonair Social Club features a roster of rotating theme nights and performances that aim to blend art, music ... more
1575 North Milwaukee Avenue
Chicago, IL 60622
20s / 30s / Acoustic / Ambient Jazz
Party Earth Review Originally opened in 1993 as a quaint deli, The Bongo Room has since evolved into one of the city’s most recognized brunch spots. Nestled among the record stores and vintage clothing ... more
1470 North Milwaukee Avenue
Chicago, IL 60622
20s / 30s / ATM / After Work / DJ / House
Party Earth Review The only “subterranean” thing about this popular live music venue is the string of prohibition-era tunnels secreted away beneath the hundred-year-old building’s foundation, long forgotten ... more
2011 West North Avenue
Chicago, IL 60647
30s / 40s / Ambient / Bar / Blouses
Party Earth Review Camouflaged behind a colorful plank façade adorned with an ever-changing display of graffiti art, The Violet Hour offers an unexpected touch of upscale luxury to a neighborhood better ... more
1520 North Damen Avenue
Chicago, IL 60622
20s / 30s / Anything goes / Brunch
Party Earth Review Half upscale sports bar, half restaurant, and one hundred percent not the typical Division Street hipster locale, The Fifty/50 draws a loyal clientele of sports fans, young professionals ... more
2047 West Division Street
Chicago, IL 60622
20s / Anything goes / Artists / TVs
Party Earth Review For lazy warm-weather days, Division Street in Wicker Park is an excellent place to while away the hours with a late brunch, drinks in a crowded game-day sports bars, some window shopping ... more
1600–2100 West Division Street
Chicago, IL 60622
30s / Ambient / Artsy / Asian Food
Party Earth Review Science fiction buffs will easily recall that “Rodan” was the name of a mutated pterosaur made famous in the Godzilla movies. The refined hipster patrons at this upscale lounge of the ... more
1530 North Milwaukee Avenue
Chicago, IL, 60622
30s / Cover charge / Creative / DJ
Party Earth Review Literally hidden down an industrial alley and sandwiched between a sea of factories and abandoned brick buildings, The Hideout has been doling out liquor and live beats since the ... more
1354 West Wabansia Avenue
Chicago, IL 60642
20s / 30s / Affluent / Ambient / Bar
Party Earth Review Seasonal cocktails and a unique Mediterranean menu that changes daily have made The Bristol a popular neighborhood eatery where laid-back foodies and young professionals go for a taste ... more
2152 North Damen Avenue
Chicago, IL 60647