Chicago's best property management company, providing tenant screening, rent collection, property marketing, and more at reasonable cost.
Chicago Property Management at its best!
Three Pentacles – Expert Property Management Company in Chicago, IL
Looking for reliable property management in Chicago, IL? Three Pentacles is a trusted property management company specializing in both residential property management and commercial property management throughout Chicago and the surrounding areas. We deliver personalized, professional property management services tailored to meet the unique needs of property owners. Whether you’re managing a single-family home, apartment complex, retail space, or office building, Three Pentacles provides the hands-on support and local expertise you can count on.
Bring your rental property to a new level! Get in touch now!
We Manage All Types of Properties in Chicago
Our City of Chicago Service Area
About Chicago
Indigenous Chicago
Chicago is the traditional homelands of Hoocąk (Winnebago/Ho’Chunk), Jiwere (Otoe), Nutachi (Missouria), and Baxoje (Iowas); Kiash Matchitiwuk (Menominee); Meshkwahkîha (Meskwaki); Asâkîwaki (Sauk); Myaamiaki (Miami), Waayaahtanwaki (Wea), and Peeyankihšiaki (Piankashaw); Kiikaapoi (Kickapoo); Inoka (Illini Confederacy); Anishinaabeg (Ojibwe), Odawak (Odawa), and Bodéwadmik (Potawatomi). Seated atop a continental divide, the Chicago region is located at the intersection of several great waterways, leading the area to become the site of travel and healing for many Tribes.
The City understands that Tribes are sovereign Nations and should have the first voice in acknowledging their historical and contemporary presence on this land. If your Tribe would like to see changes, please reach out to us for comments.
Early Chicago
Chicago’s first permanent non-indigenous resident was a trader named Jean Baptiste Point du Sable, a free black man from Haiti whose father was a French sailor and whose mother as an African slave, he came here in the 1770s via the Mississippi River from New Orleans with his Native American wife, and their home stood at the mouth of the Chicago River. In 1803, the U.S. government-built Fort Dearborn at what is now the corner of Michigan Avenue and Wacker Drive (look for the bronze markers in the pavement). It was destroyed in 1812 following the Battle of Fort Dearborn, rebuilt in 1816, and permanently demolished in 1857.
A Trading Center
Incorporated as a city in 1837, Chicago was ideally situated to take advantage of the trading possibilities created by the nation’s westward expansion. The completion of the Illinois & Michigan Canal in 1848 created a water link between the Great Lakes and the Mississippi River, but the canal was soon rendered obsolete by railroads. Today, 50 percent of U.S. rail freight continues to pass through Chicago, even as the city has become the nation’s busiest aviation center, thanks to O’Hare and Midway International airports.
The Great Fire of 1871
As Chicago grew, its residents took heroic measures to keep pace. In the 1850s, they raised many of the streets five to eight feet to install a sewer system – and then raised the buildings, as well. Unfortunately, the buildings, streets and sidewalks were made of wood, and most of them burned to the ground in the Great Chicago Fire of 1871. The Chicago Fire Department training academy at 558 W. DeKoven St. is on the site of the O’Leary property where the fire began. The Chicago Water Tower and Pumping Station at Michigan and Chicago avenues are among the few buildings to have survived the fire.
“The White City”
Chicago rebuilt quickly. Much of the debris was dumped into Lake Michigan as landfill, forming the underpinnings for what is now Grant Park, Millennium Park and the Art Institute of Chicago. Only 22 years later, Chicago celebrated its comeback by holding the World’s Columbian Exposition of 1893, with its memorable “White City.” One of the Exposition buildings was rebuilt to become the Museum of Science and Industry. Chicago refused to be discouraged even by the Great Depression. In 1933 and 1934, the city held an equally successful Century of Progress Exposition on Northerly Island.
WHY WE'RE DIFFERENT
Our guarantees give you peace of mind, knowing your property is in good hands and that we’re working hard to protect and enhance its value.
With Three Pentacles, PLLC, you’ll have a single point of contact—no more being passed from one representative to another just to get updates on your property. You’ll work directly with a dedicated Asset Manager who knows your property inside and out.
Since 2010, Arthur has served as an Illinois Receiver, managing properties in receivership in both Illinois state courts and the U.S. District Court for the Northern District of Illinois.
We have been closely working with attorneys, judges, and banks. Our managing broker has been an Associate Member of the Chicago Bar Association since 2012.
We are Real Experts in Real Estate™, experienced in property management, real estate investing, mortgages, title insurance, construction, and real estate law. Obtained the following real estate designations and certifications: CCIM, CAI, AARE, PRI, CNE, CIPS, CRB, CRS, GRI, ABR, RECS, SRES, ePRO.
Don’t settle for a typical 9-to-5, Monday-through-Friday property management company—Three Pentacles goes the extra mile, working for you 7 days a week to maximize the value of your property.
Our managing broker is a graduate of an Air Force Academy with a background in aviation engineering. This foundation brings a systems-oriented approach, strong discipline, and sharp analytical skills to our work—enabling us to efficiently help property owners improve and turn around their assets.
We perform tenant screening and background checks using a Private Detective Agency.
We combine modern technology, online-systems, and decades of real estate experience with old fashion values. We run this company the way our grandparents taught us: “Anything worth doing, is worth doing right.” TM
Our team has helped landlords throughout Chicagoland and across Illinois maximize the value of their real estate investments. Let us put our expertise and dedication to work for you, too!
Arthur holds the equivalent of two doctorates in real estate through advanced professional designations:
CCIM Designation (2000): In 2000, Arthur earned the prestigious Certified Commercial Investment Member (CCIM) designation from the CCIM Institute. This designation is awarded upon completion of a rigorous graduate-level curriculum and demonstration of extensive qualifying experience. Recognized globally, CCIM professionals are regarded as experts in commercial and investment real estate.
CAI Designation (2010): In 2010, Arthur completed the Certified Auctioneers Institute (CAI) program at Indiana University. This graduate-level program focuses on asset liquidation and auction strategies, and is the highest professional designation in the auction industry.
Since earning his CAI designation, Arthur has served as a court-appointed Receiver in Illinois, managing distressed and litigated properties under the jurisdiction of both state and federal courts.
We understand the ins and outs of local real estate
Cook County
Three Pentacles, PLLC provides property management services across North and Northwest areas of Cook County, Illinois. Our experienced team understands the unique needs of property owners and tenants in North and Northwest areas of Cook County, offering tailored solutions that ensure success:
DuPage County
Three Pentacles, PLLC provides property management services in DuPage County, Illinois. Three Pentacles manages residential properties and commercial properties in DuPage County, IL. For more information see communities listed below:
- Addison
- Bloomingdale
- Darien
- Glen Ellyn
- Lisle
- Roselle
- Wayne
- Winfield
- Aurora
- Bolingbrook
- Downers Grove
- Hanover Park
- Lombard
- Schaumburg
- West Chicago
- Wood Dale
- Bartlett
- Burr Ridge
- Elk Grove Village
- Hinsdale
- Naperville
- St. Charles
- Westmont
- Woodridge
- Batavia
- Carol Stream
- Elmhurst
- Itasca
- Oak Brook
- Villa Park
- Wheaton
- Bensenville
- Clarendon Hills
- Glendale Heights
- Lemont
- Oakbrook Terrace
- Warrenville
- Willowbrook
Lake County
Three Pentacles, PLLC provides property management services to property owners in Lake County, Illinois. Three Pentacles manages residential properties and commercial properties in Lake County, IL. For details see communities listed below:
- Antioch
- Buffalo Grove
- Grayslake
- Highland Park
- Lake Barrington
- Lakemoor
- Mettawa
- Port Barrington
- Round Lake Park
- Wadsworth
- Bannockburn
- Deer Park
- Green Oaks
- Highwood
- Lake Bluff
- Libertyville
- Mundelein
- Riverwoods
- Third Lake
- Wauconda
- Barrington
- Deerfield
- Gurnee
- Indian Creek
- Lake Forest
- Lincolnshire
- North Barrington
- Round Lake
- Tower Lakes
- Waukegan
- Barrington Hills
- Fox Lake
- Hainesville
- Island Lake
- Lake Villa
- Lindenhurst
- Old Mill Creek
- Round Lake Beach
- Vernon Hills
- Wheeling
- Beach Park
- Fox River Grove
- Hawthorn Woods
- Kildeer
- Lake Zurich
- Long Grove
- Park City
- Round Lake Heights
- Volo
- Winthrop Harbor
McHenry County
Three Pentacles, PLLC provides property management services in McHenry County, Illinois. Three Pentacles manages residential properties and commercial properties in McHenry County, IL. For more information see communities listed below:
- Algonquin
- Huntley
- Barrington Hills
- Island Lake
- Cary
- Lake in the Hills
- Crystal Lake
- Lakemoor
- Fox River Grove
Kane County
Three Pentacles, PLLC provides property management services in Kane County, Illinois. Three Pentacles manages residential properties and commercial properties in Kane County, IL. For more information see communities listed below:
- Batavia
- North Aurora
- Carpentersville
- Sleepy Hollow
- East Dundee
- South Elgin
- Elgin
- St. Charles
- Geneva
- West Dundee
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