A Walking Tour of Wicker Park

April 20, 2023

Top Art, Dining, Nightlife & Walking Tour Spots

Known as one of the hippest neighborhoods in Chicago, Wicker Park features an endless variety of art galleries, vintage stores, bustling restaurants, and trendy bars. While some of its best entertainment and nightlife venues should be explored in the evening, there’s no shortage of local businesses and stunning architecture to take a look at during the day. Here’s a list of some of our favorite spots in Wicker Park for your next walking tour.

Stan’s Donuts & Coffee

1560 N Damen Ave, Chicago, IL 60622

After getting off at Damen Station, start your tour off right at one of Chicago’s finest donut chains. Opened in 2014, Stan’s Donuts is already a classic and serves gourmet donuts, milkshakes, coffee, and small bites to eat at 16 locations across the city. Choose from over 40 flavors when you stop by, including Carrot Cake, Buttercream Bismark, and Pistachio Glazed. And for those looking to get a cute picture with a 50s vibe to it, this particular store is perfect for one.

The Robey

2018 W North Ave, Chicago, IL 60647

This might be one of the most recognizable hotels in all of Chicago. Purchased in 2012 to be restored and later transformed into a hotel in 2016, The Robey is the only skyscraper on this side of town and stands 203 ft. tall. The original building represents the Art Deco decorative style of the 1920s and 30s with bold, geometric outlines and forms. Its name takes after Robey Street, the original name of Damen Avenue. If you ever have guests coming into the city or simply want an escape close to home, enjoy two cocktail bars, a rooftop pool, a restaurant for daily brunch and dinner, and 89 hotel rooms to choose from. 


Wicker Park

1425 N Damen Ave, Chicago, IL 60622

Nearly 5 acres with plenty to do, Wicker Park is the neighborhood’s go-to spot for sports, picnics, movies, and more. Its name comes from Charles and Joel Wicker, two developers and politicians who donated the park to the city in 1870. One of its most prominent features is its beautiful gardens, tended to by the Wicker Park Garden Club that meets weekly and is open to all interested gardeners. Make the most out of the park by visiting fun events for people of all ages, with live music concerts during the seasonal farmers market, plant sales, a dog-friendly area, basketball courts, and sports fields. In the summer, grab some popcorn and enjoy the popular Movies in the Park screenings!


Myopic Books

1564 N Milwaukee Ave, Chicago, IL 60622

For book lovers, Myopic Books is a must-see on your walking tour of Wicker Park. Standing three stories tall, the bookstore has over 60,000 used books to choose from and is one of the oldest and largest bookstores in the city. They’re open seven days a week and their staff is more than happy to offer up some fantastic book recommendations. Stop here for your next great read, and if you have books of your own to contribute, they also buy gently used books for cash or store credit. 


St. Mary of the Angels Church

1850 N Hermitage Ave, Chicago, IL 60622

Our northernmost spot on the list, St. Mary of the Angels Catholic Church is one of the area’s most stunning structures and is considered one of the finest Roman Renaissance architectural pieces in the United States. Completed in 1920, it’s only one of fourteen churches built by Worthmann & Steinbach, a Chicago-based architectural firm from the early 1900s that is best known for its design of Roman Catholic, Eastern Catholic, and Lutheran churches. It was originally founded by the Polish and still holds mass in Polish, English, and Spanish to hundreds of local residents each week. Stop by, take in its beauty, and don’t miss out on seeing its 125-feet dome from the interior. 


The 606

North Leavitt St and Bloomingdale Trail, Chicago, IL 60647

Our last stop on the list is The 606, easily accessible in Wicker Park from the Damen Access Point. Originally a railroad constructed in 1873 and now a repurposed bike and running path, The 606 stretches for 2.7 miles through five different neighborhoods of Chicago. It officially opened in 2015 after over a decade in the making and is the preferred path for thousands of walkers, joggers, runners, and bikers in the area. This is the perfect place to finish our walking tour, especially if you choose to extend it to the nearby neighborhoods in Chicago!

Wicker Park is a neighborhood that you don’t want to miss out on seeing up close and personal. Reside offers a variety of communities in the area, including ones conveniently located near our favorite spots listed above. 


We hope you’ll enjoy taking a look at the sights around the area, and have fun exploring more of Chicago’s neighborhoods by foot after visiting our other walking tours on our blog.

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