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Neighborhoods
Wicker Park / Bucktown, Chicago, IL

Wicker Park / Bucktown, Chicago, IL

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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.

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What to Do in Wicker Park / Bucktown

Emporium Arcade Bar

30s / 40s / Alternative Music / Fun

Party Earth Review Entering Emporium Arcade Bar is like taking a step back into childhood, where frustrations brewed over unsaved princesses, Q*bert blew projectiles out his nose, and the only way to ... more

1366 North Milwaukee Avenue
Chicago, IL 60622

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The Fifty/50

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

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The Bongo Room

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

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Map Room

20s / 30s / 40s / Alternative Rock

Party Earth Review Self-styled as a place for weary travelers to kick back and share tales of the road, Map Room is indeed a relaxed and comfy hangout popular with both daily regulars and adventurous ... more

1949 North Hoyne Avenue
Chicago, IL 60647

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Double Door

20s / 30s / 40s / ATM / Balcony / Bar / Club

Party Earth Review Named for its two separate entrances – one for the fans and one for the bands – Double Door is a simple club where music undeniably takes center stage. With its single long bar the ... more

1572 North Milwaukee Avenue
Chicago, IL 60622

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Rodan

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

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The Violet Hour

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

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The Charleston

20s / 30s / 40s / 90s Music / ATM / Bar / DJ

Party Earth Review Centered on a residential stretch of Hoyne Avenue, The Charleston is a mellow neighborhood bar with a vintage feel that provides a welcome haven for midweek relaxation and low-key weekends ... more

2076 North Hoyne Avenue
Chicago, IL 60608

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The Flat Iron

20s / 30s / ATM / Anything goes / Bar

Party Earth Review With a rich history in the arts and music scene, The Flat Iron, formerly the live music venue The Blue Note, draws a dedicated community of creative patrons. The giant face of a skull ... more

1565 North Milwaukee Avenue
Chicago, IL 60622

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Piece

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

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Big Star

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

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Debonair Social Club

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

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