Top 7 Things to Do in Wicker Park and Bucktown, Chicago

There are many things to do in Wicker Park and Bucktown – sister neighborhoods that are among the most interesting to visit in Chicago. While Wicker Park and Bucktown have maintained much of their historical appearance, when you travel the streets of these districts, it isn’t hard to ignore the sheer amount of development that has been going on here over the past decade. If anything, this modernization has made Wicker Park and Bucktown not only more attractive to the hipster crowd and those who want to immerse themselves in the local music and arts scenes, the neighborhoods have become more family–friendly as well.

Asrai Garden

Asrai Garden is undoubtedly one of the most unique shopping experiences you will ever have. Imagine flower shops, clothing boutiques and fortune tellers – all under one roof. Yes, that’s exactly what you’ll find here. There’s also an awesome restaurant that serves some of the best salads in all of Chicago.

The 606

During your stay in Bucktown, the elevated Bloomingdale Trail (part of the Chicago Transit Authority) runs east-west to several equally cool neighborhoods, including Logan Square. There is a former line of track that was once used for freight cars known locally as The 606. In nice weather, you’ll see many folks out there running, walking, exercising and just taking it easy. There’s also an art gallery featuring some amazing local art.


Located in Bucktown, Presidio offers cocktails from countless countries around the world. It’s a favorite neighborhood hangout where you can sip such exquisite cocktails as Spirit of the Americas, Martinique Rhum Agricole, Brazilian cachaça, and Bolivian singani – to name a few.

Wicker Park

It should come as no surprise to anybody that this eclectic neighborhood has a park named after it. At four acres, Wicker Park may seem small, but during the warmer months, there’s no better place to be. Sit by the water fountain or play pickup basketball on the courts. There’s also a field house containing a gym and meeting rooms as well as a lush public garden.

Flatiron Arts Building

Wicker Park and Bucktown have a strong Bohemian past, which is reflected in this art gallery. On display are the finest works of art by area painters, sculptures and other artisans. The building is open to the public daily.

The Hideout

Wicker Park has a rough, somewhat seedier past as a haven for bootleggers and rum-runners during the Prohibition Era. The Hideout is a 19th Century home that was used to conceal the activities of these infamous characters from that time period. Nowadays, legal booze is served on the premises as the Hideout has become a venue for touring indie bands such as Phantom Planet. When you’re here, you’ll also have the opportunity to listen to live podcast recordings and partake in dance parties.


If you want to experience some of the best in the local music scene, Subterranean is the place to do it. Located on North Avenue, this venue is always booked with the best up and coming indie rock talent from Chicago, the U.S., and the world. You’ll find yourself amongst an energetic crowd that is the true vibe of this establishment.

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