The Old Milshire Hotel on Milwaukee Avenue Is Becoming 30 Apartments — and a Demo Permit This Week Means It's Actually Happening
By Socialhood News · Logan Square ·
Logan Square's Milwaukee Avenue corridor keeps adding to its redevelopment story, and the latest chapter involves a building that has been a neighborhood landmark for decades. An interior demolition permit was issued on October 3 for the former Milshire Hotel at 2525 N. Milwaukee Avenue, signaling that the long-discussed conversion of the historic property into 30 apartments is now actively underway.
The project has been in the planning pipeline for a while. Chicago YIMBY first reported the mixed-use redevelopment proposal at 2525 N. Milwaukee back in August 2026, detailing plans to repurpose the former hotel building into residential units. The October 3 interior demo permit — tracked by Chicago Urbanize — is the kind of milestone that turns a proposal into a construction site. Demo permits for adaptive reuse projects of this scale are typically the first hard sign that financing is closed and work is imminent, making this week's filing a meaningful step forward for a building that has sat largely underused for years.
The Milshire Hotel has a long history on Milwaukee Avenue. Its address puts it squarely in the stretch of the corridor that has seen the most concentrated activity over the past two years — steps from the Logan Square Blue Line station, near the newly redesigned plaza around the Illinois Centennial Monument, and close to a growing cluster of bars, restaurants, and development projects that have been reshaping the neighborhood's main commercial spine. Converting it to 30 apartments rather than demolishing it fits a pattern Logan Square has leaned into repeatedly: finding new residential life for older buildings with complicated histories rather than clearing the lot and starting fresh.
The Milshire project is one of several housing developments moving through various stages on or near Milwaukee Avenue simultaneously. Also tracking progress this week: a full building permit was issued earlier this fall for a new five-story mixed-use development at 1815 N. California Avenue, near the popular 606 trail. That project adds to a wave of new residential construction the neighborhood has been absorbing, with other recent approvals including a 50-unit building at 2240 N. Milwaukee and a proposed 38-unit mixed-use building at 3208 W. Armitage — the same Armitage corridor that just finished a long stretch of water-pipe construction and celebrated its comeback with the inaugural Armitage County Fair last weekend.
For residents keeping score on the neighborhood's housing supply, the timing matters. Zumper data cited in recent coverage of Logan Square showed average rents in the neighborhood reached $2,245 in August 2026 — an 11 percent jump year over year. Every new unit that comes online, whether in a converted hotel or a new five-story build, adds to a supply side that has been playing catch-up with demand in one of Chicago's most sought-after ZIP codes.
The Milshire conversion also lands in a moment when Milwaukee Avenue's physical character is visibly changing. The Milwaukee Avenue Streetscape project — which delivered 70 sidewalk extensions, new trees, dotted bike lanes, a walking path around the square, and new raised crosswalks — wrapped with a ribbon cutting on June 22. The interior demo permit at 2525 N. Milwaukee means that even as the street's public realm settles into its new configuration, the buildings lining it are still mid-transformation. The corridor, in other words, is not finished becoming whatever it is becoming.
No opening timeline for the 30-unit Milshire conversion has been announced. Interior demolition on an adaptive reuse project of this type typically runs several weeks before structural and construction work begins in earnest. Neighbors walking Milwaukee Avenue near the Logan Square Blue Line station can watch the project take shape from the street. For updates, the Chicago Department of Buildings permit tracker and Chicago Urbanize's Logan Square page are the most reliable places to follow the project's progress.
Logon Square neighbors — what do you think about the Milshire Hotel becoming 30 apartments? Are you glad to see the building get a second life, or do you have questions about what the finished project will look like and who it will serve? Share your thoughts with your neighbors on Socialhood!
Sources:
1. https://chicago.urbanize.city/neighborhood/logan-square
2. https://klopasstratton.com/blog/logan-squares-center-just-moved-into-the-street