Countless businesses have come and gone in Chicago since it became a city in 1837. But some of the longest-standing companies are family-owned, which may be one of the keys to that longevity.“Family businesses tend to be more committed to employees, so less likely to close or move facilities, which creates more job stability,” said Jennifer Pendergast, an adjunct professor and family enterprise consultant at Northwestern University’s Kellogg School of Management.We went in search of the oldest family-owned business in Chicago. The holder of that title was hard to pin down: City officials weren’t able to help because the city’s business license database only goes back to 2002. Other resources offer some clues: Preservation Chicago’s website features a list of “legacy businesses,” but the group said it’s “very much a work in progress.” Vicki TenHaken, a business professor in Michigan, also compiled a blog post listing the oldest companies in Illinois.To narrow down the field, we looked for businesses that have stayed in the city and the same family continuously. Here are the top contenders for the title.Baird & WarnerOne of the area’s best-known real estate companies, Baird & Warner traces its roots back to 1855. “We are the oldest real estate company in the United States,” President and CEO Steve Baird said. (Disclosure: He used to be Chicago Public Media’s board president. The Baird Foundation is a current sponsor of WBEZ.) “The business today is very different from what it was, obviously, in the 1850s and even 20, 30 years ago. We have evolved and changed, and we continue to change.” The lithograph shows the company’s Baird & Bradley location on LaSalle Street in the late 1800s.Baird & Warner The company’s original business was commercial mortgage banking. Now, it’s more focused on selling houses. In fact, it was Steve Baird who sold off Baird & Warner’s commercial businesses in 1997. “I joked that my grandfather probably turned over in his grave when I sold those businesses,” he said. “Every generation has kind of taken what it had at the beginning and then changed a little bit to meet what was the interest of whoever was running the company and where the opportunities were.”The company has stayed in the same family for five generations. “We’ve passed basically ownership and control of the company from one person to one person,” Baird said. The oldest child in each generation isn’t necessarily the one who ends up taking over the company: “I’m the third child. My older sister and my older brother were not interested, and I was.” Who will run the business after him is under discussion within the family, but Baird expects to continue running it for a while. “I’m 71,” he said. “This is my 44th year, but both my grandfather and my father worked for the company for over 60 years and worked into their 90s.” Steve Baird, left, and his father, John, in 1997. Steve became president of Baird & Warner following his father’s retirement in 1991.Baird & Warner But there’s reason to question whether Baird & Warner qualifies as Chicago’s oldest family business. The Baird family wasn’t involved when Lucius Olmsted started the company in 1855. Steve’s great-great-grandfather Lyman Baird started working for Olmsted in 1857 and became a partner in 1860. If you use 1860 as the starting point, Baird & Warner falls into second place.Iwan Ries & Co.The title of oldest family-owned business in the city could go to a tobacco shop in the Loop, originally called the E. Hoffman Co. when it started in 1857. In addition to a downtown store, German immigrant Edward Hoffman also manufactured pipe tobacco and cigars on the South Side. Hoffman needed help, but he didn’t have any children he could rely on, so he persuaded his nephew, Iwan Ries, to come from Germany and run the retail location for him. In 1891, Hoffman turned over ownership to Ries, who renamed the business. The Iwan Ries & Co. pipe store in 1964.Jack Lenahan/Sun-Times file “When he came over from Germany — I wish to heck we had it today — he brought with him a solid brass washing machine,” said Ries’ grandson, 87-year-old Chuck Levi, who now owns the store. “That’s how I started in this business. … He had us blending the tobacco in the washing machine.” Iwan Ries & Co. featured in the Chicago Tribune, January 13, 1957.Chicago Tribune The shop was in the Sherman House hotel in 1871, when the Great Chicago Fire burned it down. Three years later, another big fire swept across parts of downtown, and the tobacco shop burned down again. But it emerged from the ashes and has continued selling cigars and pipes for more than a century and a half.The shop has moved around the Loop several times. It’s now on the second floor at 19 S. Wabash Ave., where Chuck Levi runs it along with his son, Kevin, 54. Like many brick-and-mortar shops, Iwan Ries & Co. was hit hard by the pandemic, as well as by online competitors. It’s uncertain whether Kevin Levi’s kids will continue to run the company after him, but the pair say they hope to stay in business for a long time. Chuck Levi, left, owns Iwan Ries & Co. with his son, Kevin. Iwan Ries was Chuck Levi’s grandfather.Robert Loerzel “We don’t really venture that far from what we do and what we know,” Kevin Levi said. “We haven’t tried to over expand. We kind of just keep humming along.”“We take care of our customers,” Chuck Levi said. “We kiss their butts so they keep coming back. We give them good quality products at a fair price, and we have an enormous inventory.” Iwan Ries & Co., which began as E. Hoffman Co. in 1857.Robert Loerzel When smoking was outlawed in places like bars and restaurants in 2008, Iwan Ries added a lounge, creating a legal space for cigar, pipe and cigarette smokers to puff away. “I love the fact that I can smoke cigars,” longtime customer John Adams said. “Aren’t very many places you can do that comfortably. … I was a lawyer for many years. One of my clients was Michael Jordan, and he used to love coming here.” Honorable mention We identified a few businesses that began in Chicago but are now based in the suburbs. While these businesses can’t take the title for oldest in the city, they do have long histories in Chicagoland. A large gold front door that was once used at CD Peacock’s State Street store is now inside the lobby of Palmer House in the Loop. Scott Stewart/Sun-Times file CD Peacock first opened as the House of Peacock at 155½ Lake St. in February 1837 — a month before Chicago became a city. The jewelry shop’s vault survived the Great Chicago Fire. In the 20th century, CD Peacock had a store inside the Palmer House, but it left that space long ago. “Ironically, the CD Peacock bronze doorways, with their stylized peacocks, said to have been designed by Tiffany & Co., have now become a symbol of the Palmer House Hotel,” said Ward Miller, executive director of Preservation Chicago.But the Peacock family sold the business in 1969. As of today, CD Peacock no longer has any retail stores within the city. Of its two stores, one is at Woodfield Mall in Schaumburg and another is at Oakbrook Center in Oak Brook.Mathias Klein started Klein Tools as a blacksmith shop in downtown Chicago in 1857. His company became a leading manufacturer of lineman’s tools, including pliers and cutters. Klein Tools continues to be run by the same family — now in the fifth and sixth generations of ownership — but it’s based in Lincolnshire, with a plant in Elk Grove Village, as well as locations in Texas, Arkansas and New York. John Zengeler (bottom, second from left) opened a cleaning plant at 208 S. Clark St. in Chicago in 1857.Zengeler Cleaners John Zengeler started Zengeler Cleaners, one of the country’s oldest dry-cleaning establishments, in downtown Chicago in 1847. Still owned by the same family five generations later, Zengeler Cleaners has been headquartered in Northbrook since 1964. It has locations in Deerfield, Hubbard Woods, Northfield, Winnetka and Libertyville, but none in Chicago.To keep a business going for generations, Northwestern's Pendergast said, families need to have pride in their company. “[Family businesses] have a very long-term vision, making decisions that may not make financial sense in the short term but make sense in the long term.” More about our question-asker: Jonathan Schlesinger More about our question-askerJonathan Schlesinger lives in the north suburbs and is the Chicago urban fishing program coordinator for the Illinois Department of Natural Resources. He often drives into the city for work and passes several family businesses along the way.“So many businesses have come and gone in our city. What’s the oldest family-owned business, and what’s been their secret to making it through so many challenges?” he asked.Schlesinger didn’t expect a real estate firm or a tobacco shop to be the top contenders.“I really tip my hat to each family for being in business for so long, for weathering wars and economic downturns, for providing, apparently, a great service or product to Chicagoans and for putting Chicagoans to work,” he said. “I hope that Chicago continues to be a place where families can make a go of it and serve their community and provide meaningful jobs.”