Chicago Property Management Blog

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...

You know, when it comes to property management in Chicago, it’s easy to fall into the mindset of "keep the place clean, safe, and make sure rent gets paid." That’s what most landlords and property managers think is enough.But let me tell you — after years of doing this and after a killer podcast we just recorded with Joey Coleman, I’m convinced that thinking is exactly what’s holding a lot of...

If you own property in Chicago, or you’re planning to invest here, congratulations! You have chosen one of the most intriguing real estate markets in the country!From tenant-friendly laws to neighborhood-by-neighborhood rent dynamics, managing rental property here requires a lot more than just collecting rent.This is the reason that more and more people — from first-time Landlords to even the most seasoned investors — ...

As a property owner, your rental property is not only a source of income but also a valuable long-term investment. However, with the rise of online platforms and digital communication, rental scams have become frequent. Scammers are increasingly targeting landlords by hijacking rental listings, impersonating property managers, or manipulating the leasing process using fake identities.In this blog, we'll explore the common red f...

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...

If you're a landlord or real estate investor in Chicago, you've likely heard about the controversial Northwest Side Preservation Ordinance. Recently, on Straight Up Chicago Investor, Brie Schmidt, managing broker and owner of Second City Real Estate, took a dive deep into this ordinance and its significant implications for property owners. She’s been a Chicago landlord for 13 years and has been an investor agent with her o...

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...