Hot Spots And Happenings In Bucktown And Wicker Park

Joined at the hip, contiguously cool Bucktown and Wicker Park have long ranked high and inseparably among Chicago’s most desired neighborhoods. Not quite the Bohemian outposts they were when the arts crowd discovered them in the ‘80s, these neighborhoods retain their outsider underpinnings when it comes to adventurous nightlife, dynamic dining and funky festivals.

Whatever your flavor, Wicker Park and Bucktown will serve it to you.

The Songs Remain the Same

Consistent cornerstones of the area’s always vibrant music scene are Subterranean and The Hideout.

The former was founded in 1996 in an 1890s-era building that lived past lives as a brothel and a bathhouse and now hosts everything from local metal and punk acts to a weekly hip hop open mic. The latter, which also opened in ’96 in another century-old building, has hosted artists from Mavis Staples to Jeff Tweedy and was once dubbed a “perfect bar” by Anthony Bourdain.

The folks at The Hideout boast that the acts there “break out their instruments and play like it is the last night on earth.” It is a spirit that imbues the performers, denizens and venues of Wicker Park and Bucktown — from the venerable Phyllis’ Musical Inn to Davenport’s Piano Bar Cabaret.

Still Artsy After All These Years

Resist, please, the temptation to refer to the three-way intersection of Milwaukee, North and Damen Avenues as the Six Corners. Real Chicagoans know that designation belongs to the Portage Park confluence of Milwaukee, Irving Park Road and Cicero Avenue.

Just know that the Flatiron Arts Building anchors the intersection, functioning as something of a literal and spiritual epicenter of Wicker Park. Home to an artists’ colony founded in the 1980s, the many small galleries and studios throughout the triangular edifice throw open their doors for monthly First Friday events, making easily accessible one of Chicago’s great pockets of artistic energy. The Robey Hall extends the monthly party with drinks, music and more art.

Get Out

Wicker Park and Bucktown are eminently walkable, and outdoor events and activities are a big part of living in these neighborhoods.

Wicker Park Fest brings 40-plus bands to four stages over three days each July. The Bucktown Arts Fest draws tens of thousands of visitors each August and has for more than 30 years been an all-volunteer art fair that donates its proceeds to local school art programs.

But The 606 — an elevated former rail line stretching through Bucktown, Wicker Park, Logan Square and Humboldt Park — is the latest hub of outdoor activity in the area. Opened in 2015, The 606 is a roughly three-mile stretch of biking, running and walking trails featuring an observatory, art installations and events such as bonfires and stargazing.


Sometimes, you just want a seat and some service. Wicker Park and Bucktown can offer anything from the funky — Dove’s Luncheonette is a ‘60s-style diner serving Southern-inspired Mexican comfort food — to the slightly scandalous Bordel, a speakeasy throwback well-known for its rotating roster of burlesque performers, live jazz and magic acts.

Obviously, Wicker Park and Bucktown have everything an adventurous urbanite could want. Find your perfect place in one of these perfect neighborhoods in Mo2 Properties’ listings. See our available rentals here.

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