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The Ultimate Guide to the Best Property Management Companies in Chicago: Top Insights for 2025

The Ultimate Guide to the Best Property Management Companies in Chicago: Top Insights for 2025

The Chicago real estate market offers many opportunities for investors worldwide. Navigating the complexities of property management in Chicago requires a deep understanding of the local market and its challenges. Whether working with a professional property management company or an individual property manager, this guide provides insights to help you and your investment property succeed.

In this blog we will share open access to our almost two decades of property management experience and provide a list of who we consider the BEST out there. When we recommend another team we assure it is someone in the industry that we trust!

Real Estate property management services challenge Chicago

Why Property Management in Chicago Is Uniquely Challenging:

This is the first question you will want to understand before you choose a partner. Chicago’s rental market reflects its unique character:

  • Regulatory Complexity: Neighborhoods and suburbs each have unique rules and ordinances, from security deposit handling to zoning regulations.

  • Aging Housing Stock: The city’s long history also means many properties are older and may require frequent maintenance.

  • Tenant-Friendly Laws: Regulations heavily favor tenants, requiring managers to stay compliant.

  • Extreme Weather: We seem to get extreme weather on both ends of the spectrum and our properties need to be ready to handle it. Harsh winters and humid summers necessitate proactive maintenance.


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Choosing the Right Fit is Important

Why Too Large or Too Small a Company Can Be Bad:

Next, you will want to consider the difference between types of companies. Check out our blog Local vs. National Property Managers: Pros and Cons for Investors in Chicago and Beyond” for more on this topic:

  • Large National Companies: Managing thousands of doors across markets, they benefit from standardized processes. Since Chicago is so unique, they may struggle to adapt to Chicago’s nuances.Many national companies have setup shop in Chicago, but most typically don’t stay long. Chicago is a unique market and it’s typically beneficial for these companies to stick to other markets that allow for more standardization.

  • Local Companies: Managing fewer doors, these firms offer personalized service and local knowledge, often excelling in Chicago’s complex landscape. You still often get the technology of the big companies with the processes that work best in the specific market you are in. Being local is an extreme advantage in Chicago since the indepth knowledge of individual neighborhoods and the ins and outs of the local laws pays dividends in such a tenant friendly city.

  • Fly By Night Individuals/Companies: Yes, they might take on fewer doors, but they probably don't have the team and structures, and resources to handle the property they take on. We see a lot of clients take these options because the cost is less, however, if it is too good to be true it probably is. Given the tenant friendly laws and slow and burdensome judicial system in Cook County / Chicago, this could potentially be the most dangerous option.  

What Do I Look for in a Chicago Property Management Company and What are the Advantages?

Finding the right management company for YOU crucial. It's important to choose a company that specializes in property management rather than a real estate brokerage that also handles property management. A specialized property management firm typically offers more focused expertise and has better systems and processes to deal with the complexities of property management in Chicago / Cook County.

Key traits of Chicago Property Management Services include:

  • Comprehensive Screening: Thorough processes reduce risks and ensure quality tenants, therefore reducing the chance of eviction. This is also highly regulated so a solid tenant screening process will help reduce the possibility of getting sued for discrimination.  

  • Proactive Maintenance Management: A proven track record for handling repairs is essential, especially with Chicago’s aging housing stock.

  • Streamlined Systems: Strong processes ensure consistent service for tenants and owners. This is crucial for a successful real estate investment over the long haul.

  • Local Knowledge: Familiarity with Chicago’s neighborhoods and local laws ensures effective management. This may be the most important factor - we can’t stress this enough!

  • Strong Communication: Communication with owners, tenants, and vendors is at the foundation of what we do. 24/7 accessibility and responsiveness build trust and reliability.  

  • Reputation: Reading Google reviews and doing your due diligence provides insight into reliability and client satisfaction. Hiring a property management company is like getting into a long term relationship. You want to make sure you do your research on the front end to save yourself from dealing with any bad actors which may cost you a ton of time, money, and headaches. Most legitimate companies have public profiles and it will be relatively easy to see their performance over the long haul so this shouldn’t be difficult.

Advantages of working with a professional company:

  • Increased Rental Income: A property management company can help you maximize your rental income by setting the right rent, finding quality tenants, and minimizing vacancy periods. Their expertise in the current rental market ensures your investment property remains competitive.

  • Reduced Stress and Involvement: From maintenance requests to tenant screening, they manage the day-to-day operations, allowing you to focus on other priorities.

  • Expert Knowledge of the Local Market: A management company has extensive knowledge of the local market, which can help you make informed decisions about your investment property.

  • Access to a Network of Contacts and Resources: A company that specializes in real estate has a network of contacts and resources that can help you find suitable tenants, handle maintenance and repairs, and navigate the complex process of property management. This network ensures quality service and efficient problem-solving.

  • Improved Customer Service and Support: A property management company can provide a high level of customer service and support to both you and your tenants, which can help build trust and loyalty. Their proactive approach to managing real estate fosters positive tenant relationships and long-term occupancy.

  • Technology and Software: Better technology used well means far less headaches for you. Staying up to speed with technology in this field is important. Online tenant and owner portals now provide access to financial statements, leases, and maintenance orders, making it easier to manage rental properties effectively. Automation tools, advanced tenant screening software, and global talent enable firms to scale while maintaining high-touch service. If you’re interested, check out our blog on the top software in the property management industry: "Comparing the Titans of the Property Management Software Space: Appfolio, Buildium, & Propertyware."

What Should I Expect of Chicago Property Managers?

  • Navigating Local Regulations: Varying rules across neighborhoods and suburbs demand constant vigilance. With a property management company in place, the burden is on them to stay up to date and compliant.

  • Handling Maintenance: Aging properties may require frequent repairs, especially during extreme weather. The property manager should take care of all this on your behalf so you won’t be getting emergency calls at 2:00 in the morning if a pipe bursts because it’s 20 degrees below zero.

  • Managing Tenant Relationships: Tenant-friendly laws necessitate proactive communication to avoid conflicts.

  • Financial Reporting: Financial performance metrics, such as income and expense details, are crucial for assessing real estate investments. These metrics, paired with others, such as debt reduction, help paint a complete picture in regards to the return on investment property or portfolio.  

How Do Fees and Pricing Work?

Here are some common fee structures and pricing models used by property management companies:

  • Percentage-Based Fees: Many property management companies charge a percentage of the monthly rent, which can range from 7-10% of the gross rent.

  • Flat Fees: Some property management companies charge a flat fee per month, which can range from $100 to $250 or more, depending on the services offered.

  • A La Carte Fees: Some property management companies offer a la carte fees for specific services, such as screening, lease preparation, and maintenance and repairs for residents.

  • Discounts for Multiple Properties: Some property management companies offer discounts for multiple properties (or properties with a lot of units), which can help investors save money on management fees. This is particularly beneficial for those with a portfolio of rental units.


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What are the Property Management Regulations and Laws in Chicago?

To avoid common legal mistakes, are some key regulations and laws that property management companies and owners should be aware of:

  • Chicago Residential Landlord and Tenant Ordinance: This ordinance governs the relationship between landlords and tenants in Chicago and outlines the rights and responsibilities of both parties. This is the main document that dictates what we can and can’t do as a Landlord and/or property manager. If you own or are looking to buy rental property in the city of Chicago, I highly recommend becoming familiar with it.

  • Illinois Security Deposit Act: This act governs the use and return of security deposits in Illinois and outlines the requirements for landlords and tenants.

  • Chicago Building Code: This code governs the maintenance and repair of buildings in Chicago and outlines the requirements for investors and managers.

  • Fair Housing Act: This act prohibits discrimination in housing and outlines the requirements for property owners and managers to comply with fair housing laws.

The Top Chicago Property Management Companies

With over 15 years of expertise, managing over 4,000 rental units, we take pride in providing the highest quality Chicago property management services. Landmark currently serves a significant portion of the Chicagoland market in both the city and suburbs. We stay ahead of policy changes, offering tailored, full-service solutions to fit the unique needs of landlords and investors. Our dedication to collaboration and a strong network of industry professionals ensures that our clients are always in capable hands.

If Landmark isn’t the perfect fit, we confidently recommend other trusted property management companies in the area.

Some of the best property management companies in Chicago are:

Partner with Landmark Property Management

At Landmark Property Management, we pride ourselves on being a trusted partner for landlords and investors. With expertise in Chicago rental property management, we offer tailored solutions to maximize your investment’s potential.

Reach out today to talk to an expert! Stay ahead of evolving regulations and market trends with our free rent analysis.

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