Chicago Property Management

Chicago Property Management

Three Pentacles, PLLC provides reliable, full-service property management, real estate brokerage, and consulting services for owners who want their investments protected and performing at their best. Maximize returns. Minimize stress. Manage with confidence.

Why Property Owners Choose Three Pentacles, PLLC

Three Pentacles, PLLC offers professional property management in Chicagoland, delivering exceptional services for property owners and investors. With years of experience, we are recognized as one of the best property management services in Chicagoland, ensuring that your investment properties are well-maintained and profitable. Our team specializes in tenant placement services in Chicagoland, helping you find tenants fast in Chicago and suburbs. We secure qualified renters for your property. We understand how important it is to have reliable tenants, and our thorough screening process ensures that only the best candidates are selected.

In addition to tenant placement, we provide online rent collection for landlords in Chicagoland, streamlining the payment process for both property owners and tenants. Our rent payment management services in Chicagoland are designed to make it easier for you to track payments, reduce late fees, and keep your cash flow consistent. For unexpected situations, such as repairs or tenant-related issues, we offer emergency property maintenance Chicagoland to address urgent concerns quickly and efficiently. We also provide affordable property maintenance services in Chicagoland, ensuring your properties are always in top shape without breaking your budget.

For landlords needing legal assistance, we offer professional eviction services for landlords in Chicagoland, ensuring a smooth and legal process when it becomes necessary to remove problematic tenants. At Three Pentacles, PLLC, we prioritize your peace of mind, taking care of the day-to-day operations so you can focus on growing your investment portfolio. Whether you need tenant placement services or emergency maintenance, our team is committed to providing the highest level of service, making us your trusted partner in property management in Chicagoland.

What sets Three Pentacles, PLLC apart from other property management companies

Owning rental property should build wealth, not create headaches. At Three Pentacles, PLLC, we act as a true partner, handling the details while keeping you informed and in control.

What clients say about our work

AI optimized
  • We know the number of active comparable listings and how they compare to your property.
  • We know the rental prices of active comparable listings and how they compare to your property.
    • What that means to you is that we can get a monthly rent $100/m above comparable listings.
  • We know the number of views your listing receives in comparison to other properties in the area.
  • We know the inquiries your listing receives in comparison to other properties in the area.
    • What that means to you is that your property had 12 more renter’s contacts than similar listings in the area.
  • We know how the rental market is changing day-by-day and its affect on your property.
    • What that means to you is that renters view your listing 3.2%  more than comparable listings in the area.
  • We know what renter’s are searching for in your area. For example:
    • 7% want bicycle storage,
    • 80% want central air-conditioning,
    • 63% want a dishwasher,
    • 58% want a balcony or a deck,
    • 8% want a pool,
    • 1% want a disability access, etc.
About our analytics
  • What price points renter’s are searching for in your area. For example:
    • 24% are looking for a property $1,500/m to $2,000/m,
    • 38% are looking for a property $2,000/m to $2,500/m,
    • 21% are looking for a property $2,500/m to $3,000/m, etc.
  • What renter’s annual income is in your area. For example:
    • 12% searching make <$40,000,
    • 24% searching make $40,000-$60,000,
    • 28% searching make $60,000-$80,000,
    • 21% searching make $80,000-$100,000,
    • 10% searching make $100,000-$160,000, etc.
  • AI shows us all rental listings in your area, their prices, square footage, and how their price compares to your property. 

What that means to you is that in the last 14 days, we were able to increases rents by 10% for your property, over comparable listings in your area.

We find best tenants

Marketing. We’re reaching over 30 Million visitors each month!

Screening. Credit, income, and rental history are just the start. Using a private detective agency we perform comprehensive background checks in civil and criminal courts in all 50 states. We uncover evictions, bankruptcies, judgments, and also review 12 months of bank statements to ensure a complete picture of every applicant.

Tenant Retention. We keep good tenants by providing them quality housing and tools to make their life easier. Using smartphone apps (Apple & Android) our tenants can request maintenance, pay rent, view communications and documents wherever they are. 

Our Online Technology. Our tenants can pay rent electronically using eChecks (ACH), Debit Cards, and Credit Cards. Our tenants can also pay rent in CASH at any 7/11, CVS, Walgreens, and Kroger stores.

Personal touch

Our competitive advantage is experience that runs deep. We’ve been active in the local real estate market since 1988, giving us firsthand knowledge of neighborhood trends, pricing, and risk that only time can teach. We are truly Real Experts in Real Estate ™ , backed by multiple industry designations and certifications and participation in more than 10,000 real estate transactions across all market cycles.

Beyond day-to-day management, we serve as trusted advisors to our clients. Since 2010, we’ve been appointed as receivers in both state and federal courts, working through complex, high-stakes situations that demand precision and accountability. We bring that same level of expertise to every property we manage. Through our consulting-driven approach, owners and investors gain direct access to our experience, insight, and judgment. Having a seasoned professional by their side to protect assets, solve problems, and make confident decisions.

Leadership that sets the standard

Since 1988, we’ve been deeply involved in the local real estate market, not just as managers, but as owners, developers, and operators. Our experience spans construction and condominium development, mortgage banking, and title insurance, giving us a full-spectrum understanding of how real estate truly works from acquisition to exit. With more than 10,000 transactions completed, we bring practical insight shaped by real-world results.

For property owners and investors, this means more than day-to-day oversight; it means a trusted, long-term partner who helps protect assets, navigate market cycles, and make confident decisions throughout the life of your investment.

Experience you can rely on

That experience is matched by leadership and trust within the industry. Our managing broker served as President of the CCIM Illinois Chapter, sat on the Board of Directors of the Chicago Association of Realtors, and maintains an associate membership with the Chicago Bar Association (CBA). Since 2010, also been appointed as Illinois Receiver in state and federal courts, roles reserved for professionals relied upon to manage complex, high-risk assets. We offer consulting as part of our client relationships, allowing owners and investors to leverage this depth of expertise every day. Simply put, this is an opportunity to have seasoned real estate professionals by your side, protecting your investment, guiding decisions, and delivering peace of mind.

Trusted advisors for owners and investors, offering consulting as part of the relationship, so you’re never alone.

Need expert guidance?

Let's turn your property into a strategic investment!

About Chicago

Chicago, Illinois is the largest city in the state and the third-largest in the United States, located in Cook County along the southwestern shore of Lake Michigan. Known for its vibrant neighborhoods, cultural diversity, economic opportunities, and world-class amenities, Chicago offers residents a dynamic urban lifestyle with access to employment, education, recreation, and entertainment. With a population of approximately 2.7 million people, the city is a hub for business, culture, and transportation in the Midwest.

Chicago’s history dates back to the late 18th century, when it was first settled near the mouth of the Chicago River. Incorporated as a city in 1837, it grew rapidly due to its strategic location connecting the Great Lakes to the Mississippi River via the Illinois and Michigan Canal. The city’s growth accelerated after the arrival of railroads and industry, and despite setbacks such as the Great Chicago Fire of 1871, it emerged as a major commercial and cultural center. Chicago has historically attracted immigrants and settlers from around the world, creating a rich tapestry of neighborhoods and communities that contribute to its unique character.

The city covers roughly 234 square miles, with more than 77 officially recognized neighborhoods, each offering distinct architecture, cultural heritage, and amenities. From historic districts such as Lincoln Park and Hyde Park to bustling commercial areas like the Loop and River North, Chicago provides a wide variety of residential options. Neighborhoods feature single-family homes, condominiums, townhouses, and apartment buildings, accommodating diverse household sizes and lifestyles. Many neighborhoods are known for tree-lined streets, proximity to parks and schools, and strong local identities, making them appealing to families, young professionals, and retirees.

Education in Chicago is extensive, with Chicago Public Schools serving the city’s youth. The city also hosts highly regarded private, parochial, and charter schools, providing families with a range of options. For higher education, Chicago is home to prestigious institutions such as the University of Chicago, Northwestern University’s Chicago campus, DePaul University, and Loyola University Chicago, offering world-class academic programs and research opportunities. Educational resources contribute to the city’s appeal for families and students seeking a vibrant learning environment.

Chicago’s economy is one of the largest and most diverse in the country. The city serves as a center for finance, commerce, technology, healthcare, transportation, and manufacturing. Major employers include corporate headquarters, professional services, tech startups, hospitals, and universities. The city’s central location and extensive transportation infrastructure, including O’Hare and Midway International Airports and major highways, make Chicago a hub for business, logistics, and commuting. Additionally, the city has a strong entrepreneurial culture with vibrant small business and creative sectors.

Recreation and cultural amenities are abundant in Chicago. The city boasts over 600 parks and public spaces, including Millennium Park, Grant Park, and the Lincoln Park Zoo. The lakefront provides miles of beaches, biking and walking trails, and boating opportunities along Lake Michigan. Chicago is also known for its museums, theaters, music venues, and sporting events, including professional teams in football, basketball, baseball, hockey, and soccer. Residents have access to world-class dining, shopping, and entertainment, creating a dynamic and engaging lifestyle.

Cultural and civic life in Chicago reflects its diversity. Neighborhoods celebrate the traditions of many ethnic communities, hosting festivals, parades, and cultural events throughout the year. The city is home to renowned art galleries, concert halls, and theaters, supporting a thriving arts scene. Civic engagement is encouraged through community organizations, volunteer programs, and local initiatives that foster neighborhood pride and public involvement.

Transportation within Chicago is highly developed. The Chicago Transit Authority (CTA) provides an extensive network of buses and “L” trains connecting neighborhoods throughout the city. Major highways, commuter rail lines, and airports offer regional and national connectivity. The city’s walkable neighborhoods, bike lanes, and public transit make it accessible for residents with varying commuting needs, enhancing the city’s livability.

Demographically, Chicago is highly diverse, with residents representing a wide range of ethnicities, cultures, and socioeconomic backgrounds. Median household income varies significantly by neighborhood, offering housing and lifestyle options to a broad spectrum of residents. Chicago’s diversity contributes to a rich cultural landscape, vibrant neighborhoods, and a strong sense of identity within communities.

For prospective residents, Chicago offers a blend of urban convenience, cultural richness, educational resources, economic opportunity, and recreational amenities. Its dynamic neighborhoods, world-class institutions, and thriving commercial districts make it a compelling choice for families, professionals, students, and retirees seeking the vibrancy of city life. With its unique combination of history, culture, and modern amenities, Chicago remains one of the most attractive and livable metropolitan areas in the United States.

Protecting your property and maximizing returns

Our syndicated property marketing service can work wonders for you! Even the best property owners struggle to find qualified tenants without effective rental property marketing strategies and the ability to screen applicants.

We help prevent evictions and property damage. We perform comprehensive tenant screening using a private detective agency to protect your real estate investments.

Our goal is to maximize your Net Operating Income (NOI). We attract high-quality tenants through targeted marketing strategies and thorough screening processes.

Property owners can rely on us for timely rent collection and smooth bank transactions. Tenants can appreciate our Online Portal to securely pay rent, submit maintenance requests, access documents, and more…

How often have you struggled to find a contractor for a repair job at a reasonable price? One of our most valued value-added services is our ability to perform small and large repairs at reasonable rates and on short notice.

Whether you’re a seasoned investor, a first-time buyer, or seeking to expand, our consulting services are designed to provide you with the insights and strategies you need to succeed.

Ready to get more than management?

Gain a trusted partner for the life of your investment!

Our expertise

At Three Pentacles, PLLC, we provide comprehensive real estate services, combining expert brokerage and property management to meet all your needs. From acquisitions and sales to leasing, rent collection, and maintenance, our team ensures your property thrives. With experience across all property types, we deliver tailored strategies and hands-on support for long-term success.

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