Logo of Wicker Park Inn featuring a stylized building and sun design.

The Ultimate Guide to Things to Do in Wicker Park: A Wicker Park Inn Recommendation

Chicago offers something for everyone, from world-class museums and iconic architecture to vibrant neighborhoods and culinary delights.

As a guest at Wicker Park Inn, you’re in one of the city’s trendiest and most exciting neighborhoods. Here’s our curated guide to the best things to do in Wicker Park, focusing on local gems.

Bloomington Trail - 606 Trail

If you love the outdoors, the 606 Trail is the perfect way to experience Chicago from a different perspective. This elevated greenway stretches for nearly three miles, connecting several neighborhoods with scenic views, public art, and plenty of green spaces to relax. Rent a bike or take a leisurely walk while soaking in the city's urban beauty.

Runner on trail in the fall with fall colors and a cloudy sky

Myopic Books

This bookstore has been around for over 30 years and is the go-to for readers and book lovers.  It has three floors of winding bookcases with tight corners and secret passageways.  It truly is a Wicker Park treasure and a wonderful way to spend a lazy afternoon. 

Rows of books on a shelf

Wormhole 

It's hard to decide what I like most about the Wormhole. From the baristas who serve the most incredible espresso drinks to the DeLorean propped up above the restrooms, I also love the old Apple computer next to The Goonies poster. My heart smiles when I walk in, and I'm immediately transported back to the 1980s.

Dining area with guests seated and eating and drinking

Violet Hour

Delight in crafty cocktails at this romantic speakeasy that kick-started the trend. This bar is hidden behind an artistic mural that changes with the seasons and keeps pedestrians guessing what's inside.

Tortello

Hand-made pastas to delight the soul. This charming neighborhood pasta shop creates extraordinary culinary experiences from simple ingredients. This place was featured in The Bear and the 2024 Michelin Guide.

Den Theater

Take in a show at the Den Theater. From comedy to drama, there is something for everyone to enjoy.  Whether its a riveting play or a stand up comedian, their intimate theater makes you feel like you are part of the action

Davenport's Piano Lounge & Cabaret

This hidden gem has been entertaining audiences since the late 1990s. Just a block away from the Wicker Park Inn, Davenports has a piano lounge and cabaret stage. This intimate venue is the perfect stop to enjoy a live performance, and the staff also sings!

Wicker Park Farmers Market

Locals and visitors alike flock to this open market brimming with farm-fresh produce, artisanal baked goods, and ready-to-eat delights. There are games and music for the kids, free yoga in the park, and other activities for everyone to enjoy. It is truly a wonderful way to experience the heart of the Wicker Park community truly. The Farmers Market is held at the Wicker Park greens every Sunday, May - October, from 8 a.m. to 2 p.m.

 

For more on what to do, see our Explore page here.