Wicker Park is known as Chicago’s hipster enclave. Many creatives and young professionals are drawn to this neighbourhood, which has plenty of art galleries, hip cafés, innovative restaurants and vintage stores. Most of its Victorian buildings have been beautifully restored over the years, transforming into refined penthouses and apartments.

    Spend a few hours strolling the streets to find all sorts of bookshops and record stores. Wicker Park also greets visitors with quirky attractions seen nowhere else in Chicago. A must-see is the 606 – a 2.7-mile elevated trail with public art installations, scenic viewpoints and an observatory.

    Summer music festivals liven up the streets, concert venues, and public spaces of Wicker Park. Wicker Park Fest hosts more than 50 artists and bands on 4 stages, as well as vendors selling local food and souvenirs. There’s also a dedicated section for kids, where they can enjoy games, family-friendly activities, and snacks.

    Wicker Park in Chicago - one of the highlights of 10 Most Popular Neighbourhoods in Chicago (Read all about Chicago here)

    What are the highlights of Wicker Park?

    Wicker Park has a rather bohemian vibe, largely thanks to its many vintage shops and art galleries. A must-see is the Flatiron Arts Building, located at the intersection of Milwaukee, North, and Damen Avenues. The building dates back to the 1920s, with an antique elevator serving its 3 floors. Since 1985, it has been the city’s hub for local creatives – you’ll find around 40 art studios, an event space, a theatre and tattoo parlours.  

    Wicker (Charles, Joel) Park is a 4.74-acre recreational space on Damen Avenue. The urban park contains a children’s playground, a dog-friendly area, a fieldhouse with meeting rooms and a gym, community gardens, and basketball courts.

    The 606 is a repurposed railway line overlooking Wicker Park, Bucktown, Logan Square and Humboldt Park. This elevated route has trails for joggers and cyclists, with quirky art installations, lookout points, and public parks along its 2.7-mile stretch.

    Live music and theatrical performances are also among Wicker Park’s highlights. Enjoy contemporary musicals and plays at the Broken Nose Theatre, a pay-what-you-can company located just 0.3 miles southeast of Wicker Park. The Hideout occupies a restored balloon-frame house from the Prohibition era. The award-winning bar often hosts fun dance parties and touring bands (past performers include The White Stripes and The Bottle Rockets).

    Where to eat and drink in Wicker Park?

    It’s safe to say that Wicker Park represents Chicago’s eclectic dining scene. Milwaukee Avenue, Damen Avenue, North Avenue, and Division Street are the neighbourhood’s best areas for a fun night out in the city.

    You can choose from innovative fusion joints, cosy cafes, gastropubs, cocktail bars, and Michelin-star restaurants. Sample Tex-Mex dishes at Dove’s Luncheonette, Asian-style small plates at Mott Street, or handmade pasta at The Bristol.

    A popular nightlife venue is The Robey hotel's rooftop bar, where you can enjoy excellent cocktails with panoramic views of Wicker Park. Continue the fun late into the night at Subterranean – this 2-storey music venue hosts heavy rock and hip-hop acts on its upper floor ever night.

    Check out Emporium Arcade Bar if you love beer and retro games. This local favourite offers 24 craft beers on tap, rotating draft cocktails, and an impressive whiskey list. You can find over 45 arcade games from the 1980s and 1990s, including Mortal Combat, Super Mario Bros, and Donkey Kong.

    Good to know about Wicker Park

    Wherever you are in Chicago, you can easily get to Wicker Park by riding the CTA Blue Line. Hop off at Damen Station and start your day at the neighbourhood’s famous intersection, which takes you to the Milwaukee, North, and Damen Avenues.

    Wicker Park in Chicago

    Location: Wicker Park, Chicago, IL, USA

    Penny Wong | Compulsive Traveller

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