Distance from downtown: 5.5 miles Via: Blue Line Best for: Shopping Go: Afternoon, evening

Reckless Recordssm

RECKLESS RECORDS The Milwaukee Avenue location of Chicago record store chain (and occasional venue) Reckless Records is the beating heart of Wicker Park, a long and narrow storefront lined end to end with artifacts of the neighborhood’s musical history from posters to its first-class selection of new and used vinyl records.

MyopicBooks_kristof goeser

MYOPIC BOOKS Right in between the Double Door and Reckless Records on Milwaukee Avenue is one of Chicago’s oldest bookstores: a quiet, intimate, and deceptively massive three-story space filled with wooden floor-to-ceiling shelves and thousands of books of every genre.


DOUBLE DOOR Turning 20 this year, this former liquor store-turned-concert hall is a neighborhood staple for near-nightly live music that once hosted a secret Rolling Stones concert. Its vertical “Double Door Liquors” sign that illuminates Wicker Park’s central “Six Corners” intersection (Damen, North, and Milwaukee Avenues) makes it impossible to miss.


BIG STAR Among Wicker Park’s most popular eateries, Big Star offers a one-of-a-kind menu of artisan tacos starting at $3 and an equally appealing atmosphere; between its indoor space and huge outdoor patio (and its own food truck parked outside for the rushed, weather-pending), Big Star constantly and reliably serves dozens at a time.

Chopen Theater Chicago IL

CHOPIN THEATRE Constructed in 1918, the award-winning two-stage arts center Chopin Theatre hosts various performance companies and presents over 500 performances a year between theater, music, film, and literary readings.