Chicago is in dire financial straits. The city is, in a word, broke and facing a $1.2 billion deficit for 2026.
Instead of reining in reckless spending and trimming government waste, Mayor Brandon Johnson has decided to do what Democrats do best: raise taxes even more.
This time, Johnson is eying a corporate head tax, a "social media tax," and a "cloud tax" on electronically-delivered software.
NEW: Chicago Mayor Brandon Johnson will call for several tax hikes in his budget address today, according to a leaked copy of his press release. They include ⬇️
— Austin Berg (@Austin__Berg) October 16, 2025
🚩 Reviving Chicago’s head tax (a tax per job that the city eliminated in 2014) as a “community safety surcharge”… pic.twitter.com/iuinznKb0X
The entire post reads:
Reviving Chicago’s head tax (a tax per job that the city eliminated in 2014) as a “community safety surcharge” and imposing it on all companies employing over 100 people in Chicago.
Hiking the city’s 9% “cloud tax” on electronically delivered or cloud-hosted software. We are the only big city in the country with this type of tax, which has been cited by tech businesses as a reason not to invest in Chicago.
Expanding the city’s amusement tax to apply to social media companies, charging $0.50 per “active user” over 100,000 users in Chicago.
The head tax would charge Chicago businesses with more than 100 employees an additional $21 per employee per year.
Chicago Mayor Brandon Johnson is now proposing a new "head tax" to fix the deficit after destroying their budget.
— Geiger Capital (@Geiger_Capital) October 16, 2025
All companies employing 100+ people in Chicago will have to pay a tax of $21 per employee per month, simply for having employees.
A punishment for hiring people. pic.twitter.com/yS4OyuGvlj
A business with 100 employees would pay an additional $25,200 per year just to operate and employ people in the city of Chicago. Some of the largest employers have tens of thousands of employees. Here's a short list of those employers and the taxes they would pay every year:
- Amazon -- 33,000 employees = $693,000
- Advocate Health -- 30,700 employees = $644,700
- Northwestern Memorial Healthcare -- 29,400 employees = $617,400
- United Airlines -- 14,000 employees = $294,000
Chicago had a head tax that it did away with in 2014. At its peak, that tax was $4 per employee per year. Johnson's new tax is more than five times that peak.
The "social media tax" would levy a $0.50 tax on social media sites with more than 100,000 "active" users in Chicago. That would undoubtedly include sites like X, Facebook, TikTok, and YouTube. Who would pay this tax? The social media companies? There are roughly 2.7 million people living in Chicago, so if even half of them had a Facebook account, that would cost Meta $675,000 per year.
Or would it apply to social media users with large followings?
Reading the proposed new Chicago taxes, I'm curious what City Hall considers a "Social Media Company"?
— Josh Nelson - Sox Machine (@soxmachine_josh) October 16, 2025
I.E - If you are a popular TikTok'er or Twitter account that's based in Chicago, have an LLC, while having more than 100,000 followers, do you have to pay additional taxes? pic.twitter.com/08aq6hDwC6
It's possible, and would be unsurprising and on-brand for Chicago Democrats.
This tax would be passed on to consumers or to employees in lower wages and benefits. Companies that are right on the 100-person threshold would likely fire employees to reduce their headcount to 99 or fewer. It would be a disaster. Social media companies could easily block their sites in Chicago instead of paying the tax. The "cloud tax" already discourages tech companies from investing in Chicago.
Everyone sees the disaster that's coming, and yet Johnson and his fellow Democrats will likely move forward with this budget.
While many are balking at this progressive tax scheme, the uber-Leftist Chicago Teachers' Union (whose pension fund is also in financial trouble) insists taxing Chicago's wealthy is the way to go.
The problem in Chicago is, as always, spending. Illinois Policy Institute (IPI) outlines ways Chicago can right its fiscal ship without raising taxes:
Chicago needs to prioritize financial responsibility and restraint. A common-sense approach to budgeting would stabilize Chicago’s finances, restore confidence among job creators and encourage economic growth that expands the city’s tax base. Ensuring Chicago has a pro-growth tax and regulatory climate will be crucial for achieving long-term prosperity.To encourage economic and population growth, the city of Chicago should:
- Establish a robust pro-growth economic environment to expand the tax base – not the burden – and foster enduring fiscal health.
- Increase expenditures responsibly by capping budget growth in any year to the 10-year average growth in the consumer price index for all urban consumers.
- Right-size programs to create at least $550 million in 2026 budget savings and offset recent spending increases.
- Prioritize eliminating long-standing city job vacancies and filling critical roles, to reduce overtime costs and stop budgeting tricks enabled by backlogs of unfilled positions.
- Support constitutional pension reform for long-term budget stability and advance interim measures, such as pension buybacks.
- Secure immediate revenue without raising taxes, such as through Chicago Public Schools accountability.
Of course, this won't happen in Chicago. Last October, Johnson said being fiscally responsible was akin to supporting slavery.
NEW: Chicago's mayor Brandon Johnson says being fiscally responsible is the same as supporting slavery. The most disingenuous straw man argument ever. https://t.co/dknJDWNNOj pic.twitter.com/RSeHTOuJPo
— Jeff Orr (@JeffO773) October 7, 2024
Being fiscally responsible is one of the duties of government, of course. One they fail at, repeatedly.
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