Often called the hippest neighborhood of Chicago, Wicker Park is a postcard of vibrant urban culture. Take the L from downtown to Damen station, and in just ten minutes, you will be transported to a neighborhood that is a hallmark of modernity and progressivism. Exiting the train station, you will be at the six-corner intersection of North, Milwaukee, and Damen Avenues. Trendy boutiques, vintage records stores, and coffee shops line up the streets.
Commercial development in recent years is apparent in the area. High-end outdoor gear store Yeti moved in next to the old used book shop. Starbucks has a corner location not far from the thrift stores of the bygone era.
Among the newcomers is the Robey Hotel. Previously an office building, this Art Deco masterpiece is now a boutique hotel with historically inspired décor and a fantastic rooftop lounge that offers panoramic views of the city.
The old favorites include Violet Hour – a speakeasy bar with an original hidden entrance, well-crafted cocktails, and a dark, romantic atmosphere.
The Wormhole Coffee is a well-known establishment in the neighborhood that serves coffee, pastries, and the 80-s nostalgia (there is a full-size DeLorean on display, among other things.)
You can spend hours browsing the catalog looking for some rare items or something new to discover at Reckless Records. From mid-century vinyl to 90s VHS tapes, there is hardly anything you cannot find here.
Kara Finnegan, our associate broker and a long-term neighborhood resident keeps coming to Wicker Park even after she and her family have moved. The day Kara and I met to film our neighborhood video, she introduced me to her son, who was eager to go to their favorite lunch spot – Big Star – for tacos on a big bright outdoor patio.
Kara’s top recommendations for things to see and do in the area include:
606 Trail
Once an abandoned rail line, the 606 is a multi-use recreational path now that spans 2.7 miles, passing right through Wicker Park. Run, bike, or just explore the trail, which offers public art, open spaces, and elevated views of four distinct neighborhoods: Wicker Park, Bucktown, Humboldt Park, and Logan Square. It also is a community gathering space that hosts workshops, yoga classes, races, and concerts.
The Den Theatre
A four-stage theatre serves comedy, drama, and reasonably priced drinks in an intimate and inclusive atmosphere.
Myopic Books
Is a charming old used bookstore with friendly staff and a wide selection of reads over its three stories.
Wicker Park itself is a great place to enjoy, with a playground, community gardens, a historic fountain, a dog-friendly area, a baseball field, basketball courts, and an athletic field for soccer or football. Not in the mood for play? Just take refuge under the tree by the fountain on a hot summer day. Movie screenings, farmers’ markets, and live concerts are held in the park during the warmer months.
Wicker Park’s architecture embodies classic Chicago with worker cottages, two and three-flats, and Victorian homes. Pierce Avenue has several Victorian-style homes built from 1884 to 1903. Hermann Weinhardt’s house, built in 1888 for the German businessman, is a well-preserved gem, so elaborate that it’s hard to categorize the style of the building. The Mansion Row is a stretch of beautiful single-family homes on Hoyne Avenue north of Pierce. Many of these mansions were built by German immigrants who made a fortune in the brewing business, hence the nickname Beer Baron Row.
Come discover Wicker Park and its vibrant, eclectic streets and businesses for yourself. Surprised, entertained, delighted. You will be anything but bored.
Written By: Katie Andrews