TOMS Chicago

1611 N. Damen Ave.
Chicago, IL 60647
(773) 486-5882 View Website

You need good shoes for a walking tour and luckily the popular shoe brand TOMS has one of their five locations in Wicker Park. Not only are their alpargata-style shoes comfortable, but for every pair you buy a pair is given to a person in need. This location also offers their branded coffee where for every cup sold a day’s worth of water is given to someone in need.

Glazed and Infused

1576 N. Milwaukee Ave.
Chicago, IL 60622
312-226-5556 View Website

Chicago, hands down has the best doughnuts in the country. We don’t waste our time with Frankensteins like other cities who create the cronut. Instead, we create simple, majestic masterpieces and the evidence is in the maple bacon long john, which has an actual piece of peppered maple bacon on top. You’re welcome.

Flat Iron Arts Building

1579 N. Milwaukee Ave.
Chicago, IL 60622
312-566-9800 View Website

The heart of Wicker Park lies in this artist colony. The Holabird & Roche building itself will stay in your mind along with the countless skyscrapers in the Loop, but it’s the small artist studios on the second and third floor that set it apart. You can see some of them on the weekends, but the monthly First Friday party is the best to check out the impressive artwork, live music, and drinks.

1558 N. Hoyne Ave.

1558 N. Hoyne Ave.
Chicago, IL 60622
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Many forget that Wicker Park also holds some of the city’s most impressive homes, and it’s hard to find one more impressive than the one with a cannon out front. First home to C. Hermann Plautz, founder of the Chicago Drug and Chemical Company, in 1887, the cannon was added when the local American Legion was located there.

2137 W. Pierce Ave.

2137 W. Pierce Ave.
Chicago, IL 60622
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Another architectural highlight of the neighborhood has to be this home built for German businessman Hermann Weinhardt in 1888, whose ornate wood carvings will keep you entranced.

Wicker Park

1425 N. Damen Ave.
Chicago, IL 60622
(312) 742-7553 View Website

The neighborhood’s namesake, this dog-friendly park hosts farmer’s markets, concerts, and tours. The four-acre park was donated to the city by brothers Charles H. and Joel G. Wicker in 1870.

Jackson Junge Gallery

1389 N. Milwaukee Ave.
Chicago, IL 60622
(773) 227-7900 View Website

Not only a place to see the art of Laura Junge and get your prints framed by Chris Jackson, but this gallery has been a staple in the community as it hosts great events and showcases many up-and-coming and local artists.

Reckless Records

1532 N. Milwaukee Ave.
Chicago, IL 60622
773-235-3727 View Website

Vinyl aficionados will find real gems in this Wicker Park staple but even those who aren’t will be impressed by the extensive collection of new, used, and limited edition records. Fun Fact: Reckless was the inspiration for the Championship Vinyl store in John Cusak’s “High Fidelity,” which was shot only half a block away.

The Wicker Park Secret Agent Supply Co.

1276 N. Milwaukee Ave.
Chicago, IL 60622
773-772-8108 View Website

We have put ourselves in danger in exposing this retail establishment for what it really is—an undercover secret agent supply store. However, besides the cool spy gadgets, disguises, books, and decoders it’s nice to know that proceeds of sales go to 826 Chicago, a non-profit that offers tutoring classes to Chicago Public School students.

Antique Taco

1360 N. Milwaukee Ave.
Chicago, IL 60622
773-687-8697 View Website

The furniture may consist of repurposed items and antiques but the tacos, salads, and margaritas are nothing but fresh. We actively challenge you to find a better carnitas taco in Chicago, which of course has bacon in it that lays upon a corn tortilla made fresh every day. Enjoy it with a delicious rosemary margarita.