Wicker Park Apartments for Rent in Chicago

Browse available Wicker Park apartments for rent and homes for sale in one of Chicago’s most vibrant neighborhoods.

Wicker Park Rent Prices (2026)

Wicker Park’s housing stock features an appealing mix of vintage three-flat walk-ups, converted industrial lofts, modern new construction condos, and beautifully maintained Victorian-era buildings with original architectural details.

Living in Wicker Park

The dining and nightlife scene in Wicker Park is second to none, with an incredible concentration of chef-driven restaurants and craft cocktail bars. Start your morning at Goddess and the Baker for pastries and coffee, grab lunch at Big Star for some of the city’s best tacos and whiskey, then explore the vintage shops along Milwaukee Avenue including Myopic Books and Reckless Records. Evening options are endless—enjoy upscale American fare at The Violet Hour’s sister restaurant Balena, catch live music at Subterranean or Empty Bottle, or discover hidden speakeasy vibes at The Drifter. The neighborhood also hosts the annual Wicker Park Fest each summer, bringing together local vendors, live music, and the community’s creative spirit in Wicker Park itself.

Real estate in Wicker Park ranges from classic Chicago greystones and brick three-flats with original hardwood floors and decorative fireplaces to sleek new construction condos with floor-to-ceiling windows and modern finishes. Many vintage buildings feature quintessential Chicago details like bay windows, exposed brick walls, high ceilings, and wrap-around porches perfect for summer evenings. You’ll also find converted loft spaces in former industrial buildings, offering open floor plans and unique architectural character. Two-flats and single-family homes line the quieter residential streets, while newer mid-rise developments along Milwaukee and Ashland provide contemporary amenities like in-unit laundry, central air, and rooftop decks.

Getting Around Wicker Park

Wicker Park has excellent transit and driving options:

• CTA Train: Blue Line Damen and Blue Line Division stations provide direct access to downtown Loop, O’Hare Airport, and the West Side in under 15 minutes
• Bus Routes: #50 Damen, #56 Milwaukee, #9 Ashland, and #72 North Avenue provide extensive neighborhood connectivity
• Bike-Friendly: Protected bike lanes on Milwaukee Avenue and Damen, plus numerous Divvy bike-share stations throughout the neighborhood make cycling a popular option
• Driving: Quick access to I-90/94 (Kennedy Expressway) via North Avenue or Division Street, with downtown just 10 minutes away in off-peak hours

New Developments (2025-2026)

Wicker Park continues to grow with new construction:

• 1501 N. Ashland: 1501 N Ashland Avenue — Five-story mixed-use building with 44 apartments and ground-floor retail space
• 1704 North Milwaukee: 1704 N Milwaukee Avenue — L-shaped development featuring 58 residential units in studio through three-bedroom layouts ranging from 455 to 1,120 square feet
• Arandas Redevelopment: 1235 N Ashland Avenue — Modern apartment building replacing longtime tire shop, adding to the ongoing transformation of the Ashland Avenue corridor

What Our Clients Say

Crystal Banks, Landstar Realty Group, Inc.

5.0

Based on 45 reviews

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Scott Setzke

01:08 09 Dec 25

Crystal, and Bridget are live and GPA savers. They are efficient and honest. They aren’t going to BS you around town showing you places nobody wants or places way out of your price range. Straight Service. You don’t worry about being just a quota with them. You are treated as an individual and they really do listen to your preferences and they pay great attention to the details. They also are willing to “ask”. Landstar as a whole isn’t selling snake oil & pipe dreams. They are selling Property. First come first serve basis. ORDER UP! Thanks again to everybody!

Courtni Edmonds

22:31 09 Nov 25

I can’t sing Crystal’s praises enough for her help in getting me my apartment! She was communicative, quick in getting me approved, and so kind throughout the entire process. I really was taken care of and will be recommending to anyone I know looking to find their next home!

Barbara Gardner

00:19 08 Sep 25

Crystal listened to what I wanted and showed me a bunch of places. She was very diligent and followed up on everything. She made the whole process much much easier than it would have been without her. I would recommend her to anybody. Plus she’s fun to work with!

Catherine Farlee

18:41 09 Aug 25

Had a wonderful time working with the Land Star team! Michelle is a true joy and such a great communicator. I would highly recommend them, as it was a 10/10 experience!

Andrew Kogan

19:43 22 Jul 25

Michelle was super informative and professional! From showing to approval within a week! Seamless experience.

Khary Bausily

22:20 09 Jul 25

My experience with Landstar Realty was painless, quick, and amazing. My leasing agent Mark Smith was extremely attentive and was able to work with my extremely short timeline to find me a perfect apartment in time for work. Easy to contact and overall one of the best leasing experiences I’ve been through yet.

Asha Kirchhoff

20:32 14 May 25

Crystal is the best. She helped us buy our first home and we could not have done it without her guidance. She made us feel like family, we knew we were in good hands from day 1.

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Explore More Chicago Neighborhoods

Looking for apartments in nearby neighborhoods? Explore these areas close to Wicker Park:

• West Loop Apartments — Restaurant Row and modern high-rise living
• Logan Square Apartments — Arts scene with affordable vintage charm
• River West Apartments — Industrial lofts near downtown galleries
• Old Town Apartments — Historic architecture and vibrant entertainment scene

Ready to find your Wicker Park apartment? Contact Landstar Realty to schedule a showing today.