Chicago Property Management Blog

Why Tenant Screening Matters More Than Ever in 2025I get the opportunity to talk to Chicago and suburb real estate investors everyday and I hear the pains they create for themselves by not following the best practices you will take away in this article. Chicago has a rental market that is no stranger to change. With tenant-friendly laws expanding across the city and suburbs, the rise in rental application fraud, and market volatility du...

If there is one County in Illinois that I would tell everyone is the best county to invest in real estate in, that county would be DuPage county and within DuPage County Naperville is the largest city.Naperville is one of the top-rated suburban cities in Illinois and the Midwest. The prime location is ideal for real estate investors and Landlords. Known for its nationally ranked schools, vibrant downtown, and low crime rates, Naperville...

When it comes to managing apartment buildings in Chicago, one size definitely doesn’t fit all. As both an Investor and Property Manager myself, this resonates with me. Not every investor is the right fit, even if that Property Management Company is amazing.  Whether you're a Chicago property owner looking to delegate day-to-day operations, navigate local laws or handle maintenance requests, we can help. Choosing the right...

Understanding the Need for Chicago Property ManagementOwning rental property in Chicago comes with incredible opportunities, but also challenges that are often underestimated—especially for first-time landlords or those managing from a distance.Navigating Chicago’s specific and sometimes unforgiving rental market requires not only time but also an in-depth understanding of local regulations, tenant rights, and seasonal dynam...

If you’re a landlord in Chicago renting to Section 8 tenants, this update matters. I’m not here to scare you—but I don’t want you getting blindsided either.We’re about to hit a big shift in the Housing Choice Voucher (HCV) Program, and it’s going to hit your bottom line if you’re not prepared.Starting May 1, 2025, HACC (the Housing Authority of Cook County) is making some serious changes to...

It started with a great application—solid job, decent references. John thought he had found the perfect tenant for his Chicago rental. But within a few months, rent payments were late, complaints from neighbors started rolling in, and the property was showing signs of neglect. Before long, John found himself drowning in unpaid rent, legal battles, and mounting repair costs.As a Chicago property manager or landlord, stories like Jo...

Investing in rental property in Chicago can be a good opportunity, but understanding how to conduct a proper rental analysis is key to maximizing your investment. Whether you’re a seasoned rental property owner or a first-time investor, evaluating market conditions, rental rates, and operating expenses will help you make informed decisions. In this blog, we’ll explore essential factors of rental analysis, ensuring you maximi...

Recently, Straight Up Chicago Investor welcomed back Tom Raleigh, founding attorney of Halsted Law Group. The last time Tom appeared on the podcast was Episode 40: Navigating Chicago’s Eviction Process. After four years, he’s back to offer practical tips and solid advice for landlords on Cook County evictions in 2025 and how to stay ahead of issues.Tom offers advice on the eviction environment in Chicago. He covers typi...

Screening tenants in 2025 isn’t just about filling a vacancy—it’s about protecting your investment and maximizing your profits. With changing laws, savvier tenant scams, and an unpredictable rental market, Chicago landlords need to step up their game or risk costly mistakes. A bad tenant means unpaid rent, legal battles, and property damage. But with the right system in place, you can avoid the headaches and find the r...

The shift to remote work has reshaped numerous industries, and property management is no exception. With more professionals working from home, the demand for rental properties with specific amenities, flexible lease terms, and better property management services has grown. As a property owner, you must adapt to these changes to stay ahead of the curve.How Remote Work is Reshaping the Rental MarketRemote work has significantly alter...