Chicago Property Management Blog

Winter brings beautiful snow and holiday lights to the Chicago area, but it also brings freezing temperatures that can make homelessness life‑threatening. To protect tenants from being put out of their homes during the coldest weeks of the year, the Cook County Sheriff issues an annual Winter Eviction Moratorium. For the 2025‑26 season, this pause on evictions is combined with ongoing weather‑related delays that can last well into...

West Ridge, located on Chicago’s Far North Side, is known for its cultural diversity, affordability, and family‑oriented atmosphere. The neighborhood offers renters a wide range of housing options, from vintage courtyard apartments to larger single‑family homes. Devon Avenue serves as the cultural heart of West Ridge, with international dining and shopping that attract tenants from across the city. For landlords, this means a ...

Wheeling remains a strong rental market in Chicago’s northwest suburbs, offering modern housing, great restaurants, and quick access to major highways and Metra service. For landlords, steady demand means opportunity, but only with the right strategy. Understanding how long it takes to lease a unit, where rents are trending, and how seasonality impacts demand can help you plan ahead and protect your returns. This 2025 guide highli...

My name is Mark Ainley. I am a Chicago property manager, real estate investor, and co-host of the Straight Up Chicago Investor Podcast. Every week, I talk with landlords across the city and suburbs about challenges that usually come down to the same theme: “I did not know the village required that.”In 2025, rental licensing is one of those topics that can quietly make or break your deal as a landlord. It affects your timelin...

Lincoln Square is one of Chicago’s most family‑friendly rental markets, known for its European heritage, walkable streets, and vibrant community events. Anchored by the pedestrian‑friendly Lincoln Avenue corridor, the neighborhood offers renters a mix of vintage apartments, modern condos, and single‑family homes. Its appeal lies in the balance of culture and convenience: renters enjoy access to boutique shops, restaurants, a...

Schiller Park has long been a dependable rental market for landlords who value steady demand and convenient access to Chicago’s employment centers. Located just minutes from O’Hare and intersected by major highways, the suburb attracts renters who need proximity to work, transit, and affordable housing options. For property owners, though, success here comes from more than location. Knowing how long it typically takes to lea...

West Town has transformed from an industrial corridor into one of Chicago’s most eclectic rental markets. The neighborhood blends converted lofts, modern condos, and classic two‑flats with a thriving arts and dining scene. Tenants are drawn to its proximity to downtown, vibrant restaurants along Chicago Avenue, and easy access to the Blue Line. Unlike trend‑heavy Wicker Park, West Town appeals to renters who want a balance of ...

Prospect Heights offers a quiet suburban feel with strong renter demand fueled by its access to major highways, reputable schools, and proximity to job centers like Wheeling and Arlington Heights. It’s a community that attracts long-term tenants looking for space and value, making it a solid market for landlords focused on stability over speculation. Still, achieving consistent results here takes planning. Understanding how long i...

After nearly two decades of investing in and managing Chicago real estate, I’ve had the privilege of working in almost every pocket of the city. And while each neighborhood has its own strengths, one always rises to the top for me—Lakeview. As a property manager, investor, and someone who has watched the city evolve block by block, Lakeview stands out as one of the most dynamic, stable, and opportunity-rich areas on the Nort...

Tucked between Wicker Park and West Town, Ukrainian Village stands out as one of Chicago’s most character‑rich rental markets. The neighborhood blends historic brick two‑flats and landmark churches with a quieter, residential feel that appeals to long‑term renters seeking stability. Unlike trend‑driven areas nearby, Ukrainian Village attracts families and professionals who value community roots and classic Chicago architec...