Wicker Park is a neighborhood loved for it’s gritty, down to earth charm. I remember hanging out in Wicker Park with my brother in late 1980’s…then, considered an “off the beaten path” locale. What a difference a decade or two can make, especially in the Real Estate world!

Rent was cheap. Music and art were plentiful. My brother, Michael, used to read poetry at Estelle’s (usually after many cocktails). Once an “up and coming” area, Wicker Park has officially arrived. Wrapped up in endless urban charm, it’s still well-known for all those qualities: an epicenter for art, music, great food and lively nightlife. That is very likely the reason she was named top 5 among the nation’s hippest ‘hipster’ neighborhoods. Making it some of the most prime Real Estate in the city!

The Wicker Park housing market has found her groove, with homes and condos selling at a brisk pace. Modern design can be found in every corner of the neighborhood, blending harmoniously with the traditional brick cottages that are the mainstay of Wicker Park’s Real Estate. New construction condo buildings and loft conversions dot the neighborhood. Several conversions of beautiful old churches are worth a special look.

While you likely can’t go wrong seeing the sights in this part of town, don’t miss a few of my absolute favorite spots that make Wicker Park so special.

The Local Scene

Flatiron Arts Building

1579 N Milwaukee Ave, Chicago, IL 60622

This iconic triangular building is perhaps Wicker Park’s most notable landmark. Built in 1913 by famous architects, Holabird & Roche, this building was one of the pair’s few major works outside of downtown Chicago. Standing at the famous “6 corners” intersection, the building houses dozens of small art studios. Be sure to stop by for their First Friday walk throughs, or wander through the open galleries on Saturday and Sunday.


1509 N Milwaukee Ave, Chicago, IL 60622

Within seconds of stepping through the door, Eskell will undoubtedly have you charmed. Not only does this little shop carry a gorgeous selection of women’s clothing, they also have their very own line. There’s something for everyone in boutique, from their collection of dainty jewelry to their one-of-a-kind hostess gifts. Each trip to Eskell is a treasure.

Birchwood Kitchen

2211 W North Ave, Chicago, IL 60647

Perhaps some of the best sandwiches in the city, Birchwood Kitchen is a Wicker Park brunch & lunch staple. The service is friendly and efficient, decor is darling, and most importantly– their rotating, seasonal menu never disappoints.

Reckless Records

1532 N Milwaukee Ave, Chicago, IL 60622

Each trip to this record store leads to something new and exciting. An excellent selection of records, CD’s, and movies of all genres, this place will take you back in time with its old-school vibe. If the low prices don’t sell you, their photobooth certainly will certainly generate plenty of laughs. You simply can’t walk out of here without buying something.

Wormhole Coffee

1462 N Milwaukee Ave, Chicago, IL 60622

Coffee connoisseur meets childhood throwback, this shop is one of a kind. If you like your lattes Super Mario themed with a side of 80’s memorabilia, this place is for you. Even if you don’t, it’s worth checking out just for the superb coffee and experience alone.

Interior Define

2027 W North Ave, Chicago, IL 60647

A local furniture company that specializes in attainable luxury. If you’re in the market for a new sofa, look no further than this gem. Make a visit to their showroom on North Avenue to be swept away by the array of stunning (and often customizable) furniture, starting at just $1,200.

What do you look for in the Top Wicker Park Realtors & Real Estate Agents? Someone with a vast understanding of Chicago neighborhoods? How about an invaluable partner and fierce advocate? You should never settle for anyone who isn’t always striving to exceed your expectations!

1st time home buyer? Before shopping for a home, get great tips and to find out Debra’s answers to the top four most common questions that she receives! Click here.

If you’re looking for more information on the Wicker Park neighborhood, or a realtor to guide you through the various real estate options the area provides, I’d love to talk with you!

The Neighborhood at a glance

Boundaries: North Ave to the North, Division to the South, Ashland to the East and Western to the West.

  • Walk score: 94

    • A walker’s dream, you definitely won’t need a car for most of your daily activities.

  • Bike Score: 87

    • This area is a breeze to get around by bike, and even if you’re not a bike owner, the area has several “Divvy” stations (17 to be exact) that make it a snap to get around on two wheels.

  • Public Transit: 75

  • Accessible by the “L” Blue Line train, which provides easy access to downtown as well as the O’Hare airport. However, keep in mind, since the Blue is the only line serving the area, getting around to other locations in the city does require a train switch in the Loop, which can tack on quite a bit of time to your commute, depending on where you’re going.

  • Wicker Park is also served by several bus routes that make it easy to get around in the area.


Aside from highly sought after Real Estate, Wicker Park is in close proximity to some of the best public and private schools in Chicago, including:

  • Pritzker Elementary

  • De Diego Community Academy

  • Sabin Elementary Magnet School

  • Josephinum Academy

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