Old Town Apartments for Rent in Chicago

Old Town is one of Chicago’s most charming and historic neighborhoods, blending tree-lined streets with world-class entertainment and dining. Located just north of downtown, this vibrant community is home to the legendary Second City comedy club, the annual Old Town Art Fair, and countless boutique shops along Wells Street. With excellent CTA access via the Brown and Red Lines, Old Town offers the perfect mix of urban convenience and residential tranquility, making it a top choice for renters seeking character and culture.

Old Town Rent Prices (2026)

Old Town’s housing stock includes beautifully preserved Victorian-era walk-ups, modern high-rise apartments, converted lofts, and charming two-flats with original architectural details.

Living in Old Town

Old Town’s dining and entertainment scene is legendary. Start your morning at Nookies, a beloved breakfast spot serving fluffy pancakes and hearty omelets since 1973. For dinner, head to Twin Anchors for their famous fall-off-the-bone ribs, or enjoy upscale Italian at Topo Gigio. Comedy lovers flock to The Second City, where comedy legends like Tina Fey and Stephen Colbert got their start, while Zanies offers another stellar stand-up venue. Shop for unique finds at House of Glunz, America’s oldest wine shop, or satisfy your sweet tooth at The Fudge Pot. The Old Town School of Folk Music hosts concerts and classes, and every June, the Old Town Art Fair transforms the neighborhood into an outdoor gallery attracting thousands of art enthusiasts.

The real estate in Old Town covers a wide range of styles and eras. You’ll find everything from classic three-story brownstones with wrap-around porches and original stained glass to sleek new construction condos with floor-to-ceiling windows and rooftop decks. Vintage walk-ups feature exposed brick walls, hardwood floors, and decorative fireplaces, while renovated coach houses offer private outdoor space. Modern luxury buildings provide amenities like fitness centers, door staff, and parking, while charming two-flats and courtyard buildings maintain the neighborhood’s historic character. Whether you’re seeking a cozy studio in a vintage greystone or a spacious three-bedroom with modern finishes, Old Town’s housing options cater to every lifestyle and budget.

Getting Around Old Town

Old Town has excellent transit and driving options:

• CTA Train: Brown Line Sedgwick station provides direct access to the Loop and Ravenswood, while Red Line Clark/Division connects you to downtown and the North Side within minutes
• Bus Routes: #22 Clark, #72 North Avenue, and #156 LaSalle provide extensive neighborhood and downtown connections
• Bike-Friendly: Protected bike lanes on Wells Street and Larrabee Street make cycling safe and convenient, with multiple Divvy bike-share stations throughout the neighborhood
• Driving: Quick access to I-90/94 (Kennedy Expressway) via North Avenue, and Lake Shore Drive is just minutes east for scenic commutes along the lakefront

New Developments (2025-2026)

Old Town continues to grow with new construction:

• Old Town Canvas: 1600 N LaSalle Drive — Mixed-use development featuring luxury apartments with ground-floor retail, approved after extensive community review
• 1450 N Larrabee Development: 1450 N Larrabee Street — Proposed 525-unit mixed-income development on the former CHA site, bringing new housing options to the neighborhood
• Boutique Infill Projects: Several smaller-scale luxury condo and apartment buildings are under construction along Wells Street and Sedgwick, offering modern amenities while respecting the neighborhood’s historic character

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 Old Town:

• Lakeview Apartments — Sports bars, Wrigleyville energy, lakefront living
• Wicker Park Apartments — Trendy boutiques, nightlife, artistic community vibe
• River North Apartments — Gallery district, upscale dining, downtown proximity
• River West Apartments — Industrial lofts, emerging restaurants, creative spaces

Ready to find your Old Town apartment? Contact Landstar Realty to schedule a showing today.