Bob Dickinson


Bob Dickinson

Vice President, Commercial Sales
Greater Illinois Title Company

Bob Dickinson is a big band and classical trumpeter who majored in music performance, but he has spent the past 31 years making noise as a real estate title expert in the Chicagoland market. Inspired by his wife, who was a title expert eight years before he entered the profession, Dickinson finds that time spent playing before an audience gave him the sense of dedication that has propelled more than three decades of success. His accomplishments include building his business by bringing redevelopments to his company like Parkside of Old Town, which his client converted into an affordable mixed and market-rate housing project on the city’s North Side. The first of several phases of that multi-phase initiative cost more $100 million. Dickinson was also instrumental in the Wilson Yards redevelopment, a mixed-use property project in the heart of Uptown. These achievements have earned him distinction as a Multimillion Dollar Club honoree at his company each year for more than two decades.

“Helping my clients meet their business goals drives me to do my best,” Dickinson says. He primarily works with investors, attorneys, mortgage lenders and developers. He takes pride in knowing that the projects he supports are revitalizing Chicago and breathing new life into its neighborhoods. “I’m a firm believer that if you help enough people get what they want, then you’ll ultimately get what you want, too,” he says. “Being passionate about my work and the difference it makes in people’s lives brings me joy in knowing that what I do matters, so I can honestly say that I’m getting what I want.”

Dickinson adds that a critical element of securing a win-win-win for his clients is careful analysis of every transaction to ensure optimal outcomes. “I ask myself if and how I can make it better,” he explains. He points out that every good negotiator appreciates the art of listening because it opens one’s eyes to new perspectives that might otherwise go unnoticed. That skill has made him a top recruiter as a member of the Home Builders Association of Greater Chicago. He also cofounded the Southside Builders Association to rejuvenate the Windy City’s historic South Side.

A lifelong musician who was both an All-American college marching band member and a Walt Disney World performer, Dickinson is active with his church and volunteers with Samaritan’s Purse. He enjoys racquetball when his hectic schedule permits. But his priority remains making Chicago even greater through his work. “I have the knowledge and dedication necessary to support organizations that are making a meaningful difference in our city,” he says, “and I’m so fortunate that I can help make that happen in my professional and personal pursuits.”


Thanks to AtWater Apartments for letting us use their beautiful location for our photo shoots.

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