American Summer at Citywealth: Chicago’s enduring entrepreneurial spirit

Date: 05 Aug 2026

Karen Jones

Chicago has spent more than a century creating some of America’s greatest entrepreneurial fortunes. The city helped feed America through the Union Stock Yards and food companies that became global household names, including Kraft, Oscar Mayer, Sara Lee and Wrigley, while its manufacturing and transport industries created generations of family wealth. Today, Chicago remains America’s third-largest city and the country’s third-largest metropolitan economy, after New York and Los Angeles, generating almost US$920 billion of annual economic output. That entrepreneurial tradition continues through founders, family offices and technology businesses. Even as many affluent families establish tax residence in states such as Florida, they often retain homes, businesses and deep civic connections in Chicago, reflecting a loyalty that continues to distinguish the city’s private wealth community.

White Sox player in Georgia O’Keeffe style

Entrepreneurs first

Chicago’s wealth has long been built by entrepreneurs rather than financiers. From the railroads and the Union Stock Yards to household names including Kraft, Oscar Mayer and Sara Lee, the city’s economic success has been rooted in building businesses that supplied and fed America. That heritage continues to shape today’s private wealth market.

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The Union Stock Yard & Transit Co., or The Yards, was Chicago’s meatpacking district for more than a century, starting in 1865. The district was formed by a group of railroad companies that acquired marshland and turned it into a vast centralised processing area.

“Our clients are founders, CEOs and original risk takers,” says Jack Ablin, founding partner and chief investment officer at Cresset Capital, based in Chicago. “They’re generally in their forties, fifties and sixties.”

He says many are first-generation entrepreneurs who built successful businesses from modest beginnings and continue to invest in sectors they know well.

“They like businesses adjacent to their own. They like mature, cash-flowing industries that are relatively insensitive to the business cycle, whether that’s food, healthcare or specialist medical businesses.”

As those businesses mature, advisers increasingly find themselves discussing governance as well as investment performance.

“A lot of our work on the family office side is governance,” says Ablin. “The easiest way to align families around their values is through philanthropy.” He says many founders are focused on creating a financial safety net for their children while planning for the eventual transfer of wealth.

Federal tax policy is also shaping investment decisions. Ablin points to the restoration of 100% bonus depreciation under the OBBBA (One Big Beautiful Bill Act), which allows businesses to deduct the full cost of qualifying equipment in the year it is purchased. “We’re seeing opportunities in equipment leasing, including medical equipment and construction equipment. With 100% depreciation in year one, there’s now a huge incentive to invest.”

Tax planning has also become an increasingly important consideration. Ablin says many of his clients are highly focused on tax as their businesses mature and wealth passes to the next generation. “A lot of people relocate but retain a residence in Chicago,” says Ablin. “They change their domicile to Florida or another lower-tax state, but their businesses are still Chicago based.”

For many founders, the move is driven less by a desire to leave Chicago than by the tax advantages offered elsewhere. Businesses, employees, philanthropic commitments and family ties often remain firmly rooted in the city, illustrating the enduring loyalty many wealthy families continue to feel towards Chicago.

Yet for many successful entrepreneurs, remaining connected to Chicago is only part of the story. As businesses mature, many families are also formalising the way they manage their wealth, governance and succession, driving growing demand for sophisticated family office structures.

Tye Klooster, co-head of Katten’s Chicago Private Wealth practice, says Chicago’s long tradition of entrepreneurship continues to shape the city’s private wealth market.

“Chicago has long been home to entrepreneurial families and closely held businesses, and we’re seeing more families establish formal family office structures as their lives and wealth become increasingly complex. Whether they are navigating succession planning, liquidity events or multigenerational planning, families are looking for more integrated approaches to governance, investment oversight, tax and estate planning.”

“Family offices are becoming more than an administrative resource. They are evolving into governance frameworks that help families coordinate legal, business and generational planning while preserving wealth and legacy for the future.

“Despite its challenges, Illinois continues to be a beacon of Midwest finance and entrepreneurship. We have an educated workforce and outstanding universities. Young people want to build their careers here, and many are launching technology companies. Their founders have the potential to become the next generation of Chicago business leaders, following families such as the Wrigleys, Pritzkers, Crowns, Ryans and Mansuetos.”

Chicago’s resilience perhaps extends beyond business. The Chicago White Sox have become one of baseball’s surprise stories this season, climbing from recent struggles to lead the American League Central despite continuing to record some of the lowest attendances in Major League Baseball.

“Chicago is a terrific city,” says Ablin. “The Cubs will always be the glamour team, but the White Sox have come from nowhere to be in first place.”

A city that continues to reinvent itself

Chicago’s history is one of continual reinvention. The industries that built its first fortunes have evolved into a sophisticated ecosystem of family businesses, private capital, technology companies and family offices, while the city’s civic institutions continue to benefit from generations of entrepreneurial philanthropy.

Kim Kamin, partner and chief wealth strategist at Gresham Partners, where she leads the development and implementation of estate, wealth transfer, philanthropic, family education and fiduciary planning activities, believes Chicago’s past explains much of its present success.

“Chicago has long created and sustained great American fortunes. Its 19th-century titans, Swift, McCormick, Pullman, Field and Wrigley, packed meat, manufactured farm machinery and built retail and consumer empires here, while endowing many of the schools, museums, hospitals, orchestras and parks that still define the city. The Crowns, MacArthurs and Pritzkers followed in the 20th century, and a newer generation has emerged from companies such as Groupon, GrubHub, Braintree and Cleversafe. Today, Chicago is positioning itself for another wave of innovation through 1871, a deep angel and venture community that includes Lofty Ventures, and the 128-acre Illinois Quantum and Microelectronics Park. This is also where much of the modern family office industry took shape, with Family Office Exchange founded here in 1989. More recently, the University of Chicago Booth School of Business, where I teach in Executive Education, launched its Family Office Initiative, further deepening Chicago’s family office ecosystem. Having been born, raised and built my career here, I have seen this city’s capacity for reinvention firsthand.”

For context, the Crown family owned the Empire State Building from 1951 to 1961 and held major stakes in railroads, transport and sports teams including the Chicago Bulls and New York Yankees. John D. and Catherine T. MacArthur built a substantial fortune in Chicago through insurance and real estate, later creating the MacArthur Foundation. The Pritzkers are one of Chicago’s most prominent business and philanthropic dynasties, best known for founding the Hyatt hotel chain and producing Illinois Governor J.B. Pritzker.

Kamin adds. “The question is whether public policy will keep pace. Illinois’ US$4 million estate tax threshold is an outlier that gives wealthy families real pause about remaining here, particularly now that the federal exemption stands at US$15 million. Connecticut recognised this competitive reality and matched the federal level; Illinois should do the same. The cost of inaction is not theoretical. When Ken Griffin moved Citadel’s headquarters to Miami, Illinois lost one of its largest individual taxpayers, many high-paying jobs and one of Chicago’s most generous civic benefactors. Illinois has now compounded the problem by enacting a new tax on digital-asset activity that founders and investors warn is counterproductive, reinforcing the perception that emerging industries may find a more welcoming home elsewhere. So yes, Chicago needs to compete, and not merely for billionaires, but for the founders, investors and multigenerational families who want world-class universities, sophisticated advisers, cultural depth and a diverse talent base. The good news is that we already have those advantages in abundance. I remain genuinely optimistic about this city’s future, but that optimism must be matched by elected officials willing to pair our strengths with a pro-growth tax and regulatory environment that encourages people to build, invest and stay.”

A quieter technology story

Chicago’s technology sector has grown steadily, if less noisily than those of Silicon Valley or Boston.

As Susan Winer, principal and co-founder of Strategic Philanthropy Ltd, observes: “Chicago has been building a technology hub and attracting both entrepreneurs and tech companies for many years, but mostly under the radar. It’s not as glitzy as Silicon Valley or as academically driven as Boston. It is, I think, very Midwest in its approach to both supporting and encouraging innovation.”

She points to Chicago Innovation, which has supported entrepreneurs for around 25 years, together with the Illinois Institute of Technology’s University Technology Park, the Polsky Center at the University of Chicago, Northwestern University’s Garage, Techstars Chicago and 1871 in the Merchandise Mart, all of which have helped foster the city’s start-up ecosystem.

“Google and Salesforce have both established offices in Chicago, reflecting the city’s growing importance as a technology hub for the Midwest,” she says, although she believes, like Kamin, that Illinois has not promoted those strengths as effectively as competing regions.

Estate planning and policy choices

Federal tax reform has increased the US estate tax exemption to US$15 million per person, but advisers stress that state taxes remain highly relevant.

J. Devin Birmingham, managing director and estate planning consultant at Howden Private Wealth, notes that Illinois’ US$4 million estate tax threshold continues to influence succession planning for successful business owners and internationally mobile families. For advisers working across jurisdictions, understanding both federal and state tax regimes has become increasingly important. He adds. “Liquidity is often the missing piece in succession planning. Many wealthy families hold significant value in businesses, real estate and other illiquid assets. Without advance planning, an estate may be forced to sell at an inopportune time. Life insurance has become increasingly relevant for internationally mobile families, evolving from a protection product into a strategic wealth planning tool.”

The scale of the opportunity is immense. Cerulli Associates estimates that US$124 trillion will change hands across the United States by 2048, with US$105 trillion passing directly to heirs. On a simple population basis, that could equate to around US$3.4 trillion of wealth changing hands in the Chicago metropolitan area alone, underlining the importance of succession planning, governance and trusted advice particular for family businesses who may have up to 80% of their wealth tied up in day to day operations.

Those issues are likely to feature prominently as Illinois heads into this year’s gubernatorial election. Governor J.B. Pritzker is seeking a third term, with taxation, economic competitiveness and attracting investment expected to remain central themes of the campaign. For Chicago’s private wealth community, the debate extends beyond party politics to the wider question of whether Illinois can continue to compete with lower-tax states such as Florida and Texas for entrepreneurs, family businesses and long-term investment.

That question runs throughout the views expressed by the advisers interviewed for this feature. While they remain overwhelmingly optimistic about Chicago’s long-term prospects, they also believe that maintaining a competitive tax and regulatory environment will be critical if the city is to retain the founders and multigenerational families who have driven its success for more than a century. Also to attract future tech entrepreneurs. 

Looking ahead

Chicago has always rewarded people who build businesses. From the stockyards and railroads that transformed America’s food supply to today’s founders, family offices and technology entrepreneurs, its wealth has been rooted in enterprise rather than financial engineering.

Competition from states such as Florida and Texas is real, but so too are Chicago’s enduring strengths: globally recognised universities, deep pools of professional expertise, a growing innovation economy and generations of civic philanthropy. As Jack Ablin’s clients demonstrate, many of the city’s wealth creators may choose to change their tax domicile, but they continue to build companies, support institutions and invest in the city where their businesses, and often their families, first took root.

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