Chicago Property Management Blog

If you’re looking to grow your rental property portfolio in Chicago, expanding can be a great way to boost your rental income and build long-term wealth. But managing multiple properties isn’t as simple as owning one; it comes with unique challenges that require careful planning, smart strategies, and attention to detail. Whether you’re a seasoned real estate investor or just starting to grow your holdings, unders...

I love this pocket of the city and this is where my Co-host for our podcast Straight Up Chicago Investor grew up so I hear how great it is all the time directly from Tom ShallcrossDunning, located on Chicago’s Far Northwest Side, is known for its quiet residential streets, bungalow housing stock, and affordability compared to nearby suburbs. The neighborhood attracts families, retirees, and long‑term renters who value stability ...

Edison Park, located on Chicago’s Far Northwest Side, is known for its suburban atmosphere, family‑friendly vibe, and strong community identity. With tree‑lined streets, single‑family homes, and a small‑town feel, the neighborhood attracts long‑term renters who want the benefits of city living with the quiet of the suburbs. Its proximity to O’Hare and Metra makes it convenient for commuters, while local restau...

If you’ve spent any time on the Straight Up Chicago podcast, you know we’re constantly watching for the next neighborhood that quietly delivers outsized returns before the rest of the market wakes up. And right now, North Park is one of those rare opportunities hiding in plain sight. For Chicago real estate investors, small landlords, and house hackers who want strong fundamentals without paying premium pricing, North Park c...

Jefferson Park, located on Chicago’s Northwest Side, is best known for its transportation hub, affordability, and strong community feel. With the CTA Blue Line, Metra, and multiple bus routes converging here, renters enjoy easy access to downtown and O’Hare. The neighborhood offers a mix of classic bungalows, two‑flats, and mid‑rise apartments, making it attractive to families, commuters, and long‑term residents. For l...

Rogers Park, located on Chicago’s Far North Side, is defined by its lakefront living, cultural diversity, and proximity to Loyola University. The neighborhood offers renters everything from vintage courtyard apartments to high‑rise condos overlooking Lake Michigan. Its appeal lies in affordability compared to downtown, easy access to the Red Line, and a vibrant arts and dining scene along Clark Street and Howard Street. For land...

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...