Wicker Park

Wicker Park

The stretch of Milwaukee Ave. known as Wicker Park is an active buzzing part of the city. Since the 1970s, it has been a magnet for the fun and funky. With bookshops, vintage stores, fashion flagships, it is a hotbed of culture. Surrounding it are homes that are a mix between Victorian and the classic 3-flats- it just varies by block!

Nestled in between the Kennedy expressway adnand Western Avenue, the neighborhood is a great place for commuting by car or transit. The 606 trail runs right by the main intersection Milwaukee, North and Damen Aves. And Wicker Park, just south, has beautiful greenspace and activities.

After Chicago residents had to fan out of the destroyed area of the Great Fire, they made Wicker Park their home. It quickly became busy enough to warrant the blue line station established in the 1890s. Still a great community today, the history of Wicker Park can be found in architecture, the street patterns, and maybe a cobblestoned alley here and there.

Check out some of Wicker Park’s best assets!


  • Piece Pizza
    Pizza and beer go hand-in-hand at this microbrewery turned pizzeria.
  • Small Cheval
    A satellite location to its Fulton Market brother, it still has one great burger.
  • Dove’s Luncheonette
    Comfort food is served at this countertop diner with modern flair.
  • Big Star
    If you are looking for the best gourmet tacos, look no further. Fun and authentic!
  • Sultan’s
    This quick service falafel spot has a great salad bar and is a town favorite.


  • John Fluevog Shoes
    These unique shoes are the perfect “tie it all together” statement piece.
  • Ragstock
    One can find some great second-hand treasures at this famous thrift store.
  • Reckless Records
    So much vinyl to be had at this  location of Chicago’s famous record store.
  • Myopic Books
    With books towering 4 stories up, it’s hard to see that they also have readings!
  • Transit Tees
    Sport your favorite el line, or buy the newest CTA themed board game!


  • Chop Shop
    This restaurant has a surprising large stage and also hosts a slew of music fests.
  • Subterranean
    Another iconic stage in Chicago- this venue hosts any genre with gusto!
  • Davenport’s Piano Bar
    Kick back in luxury with a cocktail and some tapas at this lounge.
  • Emporium
    See some of the best live bands in Chicago. Best part? Shows are free and an arcade!
  • Gallery Cabaret
    This unassuming dive bar hosts a slew of local acts- many of which go places!

Things to Do

  • Street Festivals
    Wicker Parks hosts some of the best music and art oriented fests in the city!
  • Big Mini Putt Club
    This bar is also a 9 hole mini golf course- it’s the best combo.
  • Escape Artistry
    This escape room is an inventive way to spend an evening with friends!
  • The 606
    Chicago’s famous rails to trails path has the best stretch to bike, walk or jog.
  • The Robey
    Sporting one of the best non-skyline views in the city, grab a cocktail and savor!


  • The Den Theatre
    Putting on free shows for aspiring actors, the plays are always interesting.
  • Collaboraction Theatre
    New, bold, and engaging are used to describe this offbeat troupe.
  • Society for Arts
    This gallery introduces European art, sculpture and cinema to the USA.
  • MSA & Circus Arts
    More than just gymnastics- take classes in aerial ribbons, trapeze and more!
  • Free Street Theatre
    This troupe has battled societal injustice since 1969 with accessible art.


Explore Wicker Park

Find Your Next Wicker Park Home