Top 8 Activities to Experience in Wicker Park, Chicago

Wicker Park is one of Chicago’s hippest neighborhoods, perfect for experiencing experimental restaurants and exclusive boutiques. Historically inhabited by Polish residents, the area now boasts a diverse community. With vibrant commercial streets and an abundance of dining options, Wicker Park has something for everyone. Here are eight exceptional things to do, drink, and eat while visiting this trendy neighborhood.

Eat Tacos at Big Star

Address: 1531 N Damen Ave, Chicago, IL 60622, USA

Phone: +1 773-235-4039

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Big Star, recognizable by its giant star sign, offers delicious tacos served with an array of unique toppings such as pineapple and pumpkin seeds. Enjoy these culinary delights in a lively atmosphere, although outdoor seating can be limited during peak summer months.

Hang Out in the Park

Address: 1425 N Damen Ave, Chicago, IL 60622, USA

Phone: +1 312-742-7553

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Be sure to visit the 4-acre Wicker Park, which offers a playground, community gardens, and athletic fields. The park also hosts various events, including movie nights, music performances, and farmers markets.

Enjoy a Night Cap at Violet Hour

Address: 1520 N Damen Ave, Chicago, IL 60622, USA

Phone: +1 773-252-1500

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At The Violet Hour, guests can indulge in cocktails inspired by the pre-prohibition era. This elegantly designed bar offers seasonal drinks and even provides cocktail classes for those interested in creating their own concoctions.

Shop on Milwaukee Avenue

Milwaukee Avenue features many unique boutiques, restaurants, and cafés. For vintage clothing enthusiasts, there are several shops along one block, such as Vintage Underground and Store B. Indulge in brunch at the Bongo Room or treat yourself to ice cream at Jeni’s Splendid Ice Cream.

Walk or Bike the Bloomingdale Trail

Address: Bloomingdale Trail, Chicago, IL, USA

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The Bloomingdale Trail, part of The 606, provides a scenic 2.7-mile walking and biking path. This former railway bridge showcases various art installations and hosts events throughout the year. Additionally, guided tours are available on select dates for those wishing to learn more about the trail.

Drink and Play at Emporium Wicker Park

Address: 1366 N Milwaukee Ave, Chicago, IL 60622, USA

Phone: +1 773-697-7922

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At Emporium Wicker Park, patrons can enjoy a fun atmosphere filled with arcade games and a wide selection of drinks. The venue features nearly 50 arcade games and frequently hosts live music, creating an exciting evening experience.

Enjoy Brunch at The Bongo Room

Address: 1470 N Milwaukee Ave, Chicago, IL 60622, USA

Phone: +1 773-489-0690

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Founded by best friends Derrick Robles and John Latino, The Bongo Room offers a diverse menu of seasonal breakfast and brunch items, with options like rotating pancake flavors and signature burrito dishes.

Sip on Hot Cocoa

Address: 1623 N Milwaukee Ave, Chicago, IL 60647-5508, USA

Phone: +1 773-489-1747

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During Chicago’s chilly winters, enjoy a warm mug of hot chocolate from Mindy’s Hot Chocolate, where you can choose from seven varieties accompanied by a house-made marshmallow. If you’re feeling adventurous, consider adding a splash of brandy, whisky, rum, or cognac to your drink.