The Really Rich Aren’t Just Leaving Chicago. It’s More Complicated (Part 1: On Business)

The affluent and corporations are fleeing Chicago

Your trusty correspondent has been gallivanting around the streets of the North Side lately, chatting and kvetching with business acquaintances and old friends, trying to get a read on the top one percent (from a tax-paying perspective) of those who call the Windy City home, or at least keep a secondary property here.

This last statement deserves special attention. More and more rich Chicagoans -- many of whom still have rose-colored glasses when it comes to the city -- who saw themselves as "never leavers" have now taken up residence in either neighboring states, Florida, Tennessee, or North Carolina, having jettisoned their Burling, Orchard, and Astor properties for lower crime, lower tax and more business-friendly states of residence.

Others, I'm learning, are developing these options, especially as their children enter college or head to boarding school (or later, as they retire or begin to dial things back). After all, it won't take much if Florida abolishes property taxes for residents, in addition to the "no income tax" it provides today, for wealthy Chicagoans to save six or seven figures in taxes per year by spending six months and a day out of Illinois and the city, and downsizing their footprint here.

Incidentally, the "renting" option when Chicago becomes a non-resident, secondary city is becoming more popular among this crowd (just as some have told me, be sure to have an LLC, a company, or a friend rent it in the first year or two after moving to make sure the long arm of J.B. Pritzker's friendly tax-collecting team does not come after you).

Now, these are just stories. So take them as you may. The other day on the "All In" podcast, David Sacks reminded us, when taking the piss from a co-host, "a collection of anecdotes does not make data," so please discount this essay accordingly. But I do think from these discussions (multiple, in different social and business circles), I've gotten a good sense of where Chicago's "elite" are on issues of politics, crime, education, and the future business climate.

I'll start by saying there's no consensus on topics anymore, which is a good thing. Now, there are definitely rich virtue signaling zombies (those with personal shoppers at Neiman's and Nordstrom) infected with the anti-racist virus, even if they've given up putting their personal pronouns on their LinkedIn page.

You know the type: they still voluntarily show their TDS on full display, think "removing" books with trans-child pornography and pronoun affirmations from Latin, CPS, and Chicago libraries amounts to something infinitely worse than Nazis burning Torah scrolls, and that ICE is the devil incarnate (albeit when you peel the onion on this topic, you realize that most just don't want to pay a living wage for their domestic, house, and garden help).

The truly brainwashed ladies who lunch aside, I'll start today by focusing on the business climate in Chicago, and continue the series with elite views on taxes, crime, politics, education, and more.

As someone who personally shut down an office in Chicago (and went virtual), it would be easy to fall into the trap that Chicago is finished, on an NPV (long-horizon) basis, relative to its ability to deliver geographic alpha relative to other locations when it comes to attracting/retaining talent, regulation, profit (not EBITDA) for owners, etc.

I hear this from many people (besides the voice in my own head saying I made the right decision when I did). However, I also hear from others (some of whom now have favorable tax credits with the state, while others do not) that the business climate is not only improving, but will also comparatively outperform other regions.

One argument someone made to me, which is reasonable, is if you look at the amount of CAPEX investment going into Chicago (on the order of $30B in recent and coming years), there will absolutely be a commensurate gain in business activity (as CAPEX investment typically precedes private sector revenue growth, return on invested capital, return on net assets, or any other metric you want to use to measure returns comparatively).

Now, we also can't discount the net loss of headquarters and offices in Chicago and Illinois, which include:

Beam Suntory — relocated corporate HQ to New York City (mid-2022).

Boeing — moved global HQ to Arlington, VA (May 2022).

Caterpillar — shifted HQ from Deerfield, IL to Irving, TX (June 2022).

Citadel — Ken Griffin relocated firm and personal HQ to Miami, FL (2022).

Guggenheim Partners — quietly reducing Chicago presence.

PEAK6 Investments — moving global HQ to Austin, TX (effective Jan 2025).

Schumacher Electric Corp. — moved HQ from Chicago suburbs to Fort Worth, TX (2021).

SC Johnson — Moving approximately 170 employees from downtown Chicago to its Racine-area facility in Wisconsin by end of 2026.

TTX Company — relocating HQ from Chicago's West Loop to North Carolina (announced 2023).

Tyson Foods — closed downtown Chicago office, consolidating HQ in Arkansas (Oct 2022).

United Airlines — still nominally HQ'd in Chicago but expanding ops and leadership near Denver and signaling a potential move (including building out 100-plus acres of land in Colorado and filed a master-plan which includes up to ~1 million sq. ft. of office space on the site; the filing suggests space for as many as 6,000 employees, which would indicate an HQ-size operation).

Walgreens Boots Alliance — Plans to vacate its downtown Chicago Old Post Office office and relocate workers to its suburban Deerfield campus starting January 2026.

Conversely, new gains include:

Bally's Corporation – Building a new integrated resort/casino in Chicago's River West neighborhood, with construction beginning 2024 and opening next year (at least as planned).

Conagra Brands – Though slightly older (2016), this is a strong example of a company choosing Chicago for its global headquarters. 

Dover Corporation – Announced relocation of its corporate headquarters from New York City to Downers Grove, Illinois, (a suburb of Chicago) in 2024.

GE HealthCare  – Brought its global HQ to Chicago, consolidating major operations in the last decade.

Nautilus Solar Energy  – Announced relocation of HQ to Chicago. The solar-company will build out its presence in the region, and over the next year expects to bring 100-plus milliwatts of new solar capacity in Illinois

Newmark – Relocating its Chicago office to the new Salesforce Tower Chicago, with a move-in expected early 2026.

PsiQuantum – Selected Chicago’s “Illinois Quantum and Microelectronics Park” (IQMP) as the site for its U.S. utility-scale quantum computing campus. Broke ground this fall. 

Incidentally, as a tech geek myself (albeit one more focused on AI these days than quantum), I think the quantum buildout/investment is the most interesting to see if they can make Chicago a business powerhouse for the next computing wave. 

So yes, the exodus is real, but $30 billion in CAPEX and a casino suggest someone's betting the other way. And since, the top one percent nationally pay 46 percent of all federal income tax, Chicago/Illinois income tax, business replacement tax (don’t ask – it’s painful), property tax (and all other taxes are higher than the national average), this is indeed a leveraged bet for Chicago that can’t be overstated. 

But whether they're right or just suckers for punishment, remains to be seen.

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J.D. Busch is a tech entrepreneur, investor, and writer.