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Best Things To Do In Wicker Park

Wednesday, August 28th, 2019

Chicago, perhaps more than any other major urban metropolis, is a city of neighborhoods, each a unique flavor.

Viewed for generations as a largely ethnic mosaic, these neighborhoods still dance to different beats — but now it is culture by choice. Every Chicago neighborhood has distinct architecture, its go-to outdoor activities, its brand of dining and drinking. Whether you favor taverns or tea rooms, fine dining or funky diners, indie rock or opera, Chicago has a neighborhood for you.

There is never a shortage of things to do in Wicker Park, Chicago. This venerably chic community has been a go-to destination since the 1980s, where cheaper rents could be found. It checks more boxes than most. Here’s a short list of some of the top Wicker Park attractions:

The Parks

When “park” is part of the name, going to them ought to be among the best things to do in Wicker Park‚ and it is.

  • The 606 recreational trail is more than just a great walking and biking path connecting Wicker Park with equally enchanting enclaves such as Bucktown, Humboldt Park and Logan Square. It is an ever-changing outdoor gallery and performance space, spread over nearly 3 miles of what used to be an elevated rail line, and four of its 12 access points are in Wicker Park.
  • At 5 acres, the neighborhood’s eponymous park is a hub of activity featuring baseball, soccer and football fields; basketball courts; a fieldhouse; a children’s playground with an interactive water feature; a dog park; and ornamental community gardens.

Drinking and Dining

If you can find The Violet Hour, a devilishly discreet cocktail lounge, it’ll sizzle your swizzle with pre-prohibition libations. In addition to lining up the music acts at the wildly popular Wicker Park Fest each July, the brilliant minds behind Subterranean are busy programming their divine dive with rock, hip-hop, reggae and rap acts. The UP Room is a rooftop lounge atop the tallest building in the area, the Robey Chicago hotel, and offers spectacular views from the intimate indoor bar and terrace.

Dining spots sample tastes from around the globe, including Filipino (CEBU), Costa Rican (Irazu), Southern (Ina Mae Tavern & Packaged Goods, The Delta) and something called New Haven-style pizza (Piece). The veggie-centric are nibbling at Clever Rabbit. The adventurous never fail to find the Michelin-anointed molecular madness at Schwa.


Yes, there are major retailers along Milwaukee Avenue, but for those who appreciate urban exploration, among the best Wicker Park things to do is discover the hidden gems of its bounty of boutiques.

The Midwest’s only women-specific bike shop, BFF Bikes, makes its home in Wicker Park; as does Myopic Books®, a home to poetry nights, concerts and 80,000 used books. Asrai Garden has been wowing locals with floral arrangements, hand-crafted jewelry and exclusive apothecary items since 1999. Fashion fans flock to p.45, known for carefully curated collections of famous and emerging designers.

Find Your Place in the Park With Downtown Apartment Company

You can put all these Wicker Park, Chicago things to do at your doorstep quickly and with confidence. Browse apartments or penthouses for rent and call us today.

You can put all these activities at your doorstep quickly and with confidence.