Chicago’s Wicker Park in One Day (Yes, It Can Be Done!)

Named one of the hippest neighborhoods in the country by Forbes, Chicago’s popular and vibrant Wicker Park is awash in European-style art galleries, high-fashion boutiques, and chic eateries. Although you might think you’d have to be a resident—one with plenty of free time—to take in all the Wicker Park sights, you can actually see the best of the area in just one day. So recruit a friend, request an Uber, and hit the spots that represent all that the neighborhood offers.

Early morning: You’ll need some sustenance for the big day ahead. Fortunately, you’ve got some delicious options. Stop in at Milk & Honey Cafe, where they make their own granola and even fold it into buttermilk pancakes. (1920 W. Division Street #1)

Mid-morning: Get artsy by heading to the Flatiron Arts Building, a one-stop attraction for artist studios, tattoo shops, costume design work, and more. The building is open to the public, so you can stroll through and see artists at work. (1579 N. Milwaukee Avenue)

Late morning: Wander over to Wicker Park, a four-acre property that’s known for its lush ornamental gardens that are lovingly maintained by community volunteers. (1425 N. Damen Avenue)

Lunch: Sample a taste of old Chicago at Dove’s Luncheonette, a diner where only 1960’s and 70’s soul and blues tunes play. (1545 N. Damen Avenue)

Early Afternoon: Time to go shopping. Even if you’re not much of a shopaholic, Wicker Park can change you into one, at least temporarily. With boutiques that have fashions for men and women, plus luxury home goods, there’s an array of browsing opportunities. Try going vintage at Reckless Records, where vinyl junkies get their fix. (1379 N. Milwaukee Avenue)

Mid-afternoon: Turn getting a sugary pick-me-up into a history lesson by stopping in at Margie’s Candies. Open since 1921, this well-established neighborhood favorite has all the charm of old Chicago blended with homemade ice cream and candy. (1960 N. Western Avenue)

Happy hour: Wicker Park wouldn’t be as popular without craft beers in abundance. With so many welcoming taverns sporting an array of taps, it’s challenging to choose just one or two. But hey, who doesn’t love a challenge? Sit outside and have a pint at Pint, which offers an extensive draft selection. (1547 N. Milwaukee Ave # 7)

Dinner: If you thought picking a post-shopping cocktail spot was tough, just try narrowing down your dining options. Wicker Park is awash in top restaurants, but if you want the Chicago steakhouse experience, consider the Chop Shop. Housed in old auto body building, the eatery specializes in seasonal creations. (2033 W. North Avenue)

Evening: When deciding how to round out the day, you have everything from jazz to standup comedy. Since Chicago is a theater town, consider heading to Chopin Theater, a top venue that always has plenty going on. (1543 W. Division Street)

Late night: If you and your friend still have energy to spare, head to Subterranean, a 100-year-old building built above Prohibition-era tunnels. The club hosts live music events and rocking DJs until 2 a.m., rounding out your night into the wee hours. (2011 W. North Avenue)

At this point, you’ll have packed an entire day with Wicker Park must-see attractions, from fun eateries to zesty entertainment.

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