The fifth floor of 121 North LaSalle Street is quiet, but it’s heavy. You feel it the second you step off the elevators. That’s where the City of Chicago Office of the Mayor lives, and honestly, it’s the most powerful square footage in the entire Midwest. People think the Mayor just cuts ribbons or yells at snowplow drivers during a blizzard, but the reality is way more complicated and, frankly, a bit more chaotic than that. It’s a massive machine. It’s a gatekeeper. It’s the place where billion-dollar budgets meet neighborhood-level grievances about a broken streetlight or a permit that’s been stuck in limbo for six months.
Chicago is a "strong mayor" city. That’s not just a political science term; it’s a lifestyle. Unlike some cities where a City Manager runs the day-to-day and the mayor is just a figurehead who shows up for photo ops, the City of Chicago Office of the Mayor holds the keys to the kingdom. They control the agencies. They propose the budget. They appoint the heads of the CTA, the CPD, and the Chicago Public Schools. If something goes wrong in this city, the buck doesn't just stop at the Mayor’s desk—it basically lives there.
Who is actually in the City of Chicago Office of the Mayor?
It’s not just one person. Far from it. When we talk about the Mayor's Office, we’re talking about a sprawling team of deputy mayors, policy advisors, press secretaries, and "intergovernmental affairs" folks—which is just a fancy way of saying the people who lobby Springfield and D.C. for money.
The structure changes slightly with every administration. Brandon Johnson, the current Mayor, has leaned heavily into a "Deputy Mayor" model to divide the labor. You’ve got a Deputy Mayor for Economic and Neighborhood Development, a Deputy Mayor for Labor Relations, and even a Deputy Mayor for Immigrant, Migrant, and Refugee Rights. This matters because these are the people who actually take the meetings you’ll never get. They are the filter. If you want a new TIF (Tax Increment Financing) district or a change in zoning for a massive development in the West Loop, you aren't talking to the Mayor first. You’re talking to their deputies.
Then there’s the Chief of Staff. That’s the "enforcer" role. This person makes sure the departments aren't at war with each other, which happens more than you'd think. Imagine the Department of Water Management wanting to tear up a street the week after the Department of Transportation just paved it. That’s the kind of ego-clashing and logistical nightmare the Mayor’s Office has to settle. It’s a 24/7 job that is mostly about putting out fires before the public smells the smoke.
The Budget is the Real Power
Let’s talk money. Every year, the City of Chicago Office of the Mayor drops a multi-billion dollar budget proposal. For 2024 and 2025, we’re looking at figures north of $16 billion. That is a staggering amount of cash.
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The Mayor’s Office doesn't just spend this money; they use it to signal what they actually care about. If they say "equity" is a priority but the budget for neighborhood investment stays flat while police spending rises, people notice. This is where the tension with the City Council happens. See, the Mayor proposes, but the 50 Aldermen (or Alderpeople, if you prefer) have to approve it. In the old days—think Richard J. Daley or even the early Rahm Emanuel years—the Mayor’s Office basically dictated the budget and the Council rubber-stamped it. Now? It’s a dogfight.
The Mayor’s Office has to negotiate. They trade a playground in the 19th Ward for a vote on a property tax levy. It’s transactional. It’s Chicago.
Executive Orders and the "Stroke of a Pen"
Sometimes the Mayor doesn't want to wait for the Council. That’s when the executive orders come out. These are directives that have the force of law within the city government. Recently, we’ve seen the City of Chicago Office of the Mayor use these to create task forces on reparations, mandate environmental justice standards, or streamline how the city handles the migrant crisis.
It’s a tool of speed. But it’s also a tool that gets challenged in court constantly.
The Mayor’s Office vs. The Sister Agencies
One thing most people get wrong is thinking the Mayor has total, direct control over everything. It’s more like a loose confederation. The Chicago Transit Authority (CTA), the Chicago Housing Authority (CHA), and the Chicago Public Schools (CPS) are "sister agencies."
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They have their own boards. They have their own CEOs.
However, the City of Chicago Office of the Mayor appoints those board members. This gives the Mayor "soft power." If the CTA is failing to meet its scheduled runs—a major complaint in 2024 and 2025—the Mayor can’t technically fire a bus driver, but they can put immense pressure on the CTA President to fix it. This relationship is often strained. You'll see the Mayor’s Office publicly defending an agency one day and then privately ripping them a new one the next because a "Ghost Bus" made the Mayor look bad on the evening news.
Public Safety: The Ultimate Litmus Test
You can’t talk about the Mayor's Office without talking about the 5th floor’s relationship with the 1st District. Public safety is the single biggest issue that determines if a Mayor gets a second term. Just ask Lori Lightfoot.
The City of Chicago Office of the Mayor oversees the Chicago Police Department (CPD), but it’s a relationship defined by a Federal Consent Decree. This means a federal judge is basically watching over the Mayor’s shoulder to make sure the city is fixing systemic issues with policing. The Mayor’s Office has a dedicated public safety team that looks at the data every single morning. How many shootings? Where? What’s the clearance rate?
But Brandon Johnson’s administration has tried to shift the focus. They talk about "Treatment Not Trauma." They want the Mayor's Office to lead on mental health response, not just tactical police response. It’s a massive pivot, and the Office of the Mayor is the laboratory where this experiment is happening. Whether it works or not is the $16 billion question.
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How to actually deal with the Mayor's Office
If you’re a regular person, you’re probably never going to get a meeting with the Mayor. Sorry. But the Office of the Mayor is technically accessible. They have a "FOIA" (Freedom of Information Act) officer. You can request emails, budget drafts, and calendars. It’s one of the best ways to see who is actually influencing policy.
If you have a problem, you usually start with your Alderman. But if the problem is "The City won't give me a permit for my multi-million dollar housing project," your lawyers are going to be knocking on the door of a Deputy Mayor.
Common Misconceptions
- The Mayor controls the Parks: Mostly, but the Chicago Park District is its own taxing body with its own board. The Mayor’s Office influences it, but it’s not a department like Streets and San.
- The Mayor can raise your property taxes alone: Nope. They can propose it, but the City Council has to take the heat for the vote.
- The Office is just political: Actually, most of the staff are career policy nerds. The "political" people are a small circle; the rest are trying to figure out how to keep the city's bond rating from tanking.
Why it matters right now
We are in a weird time for Chicago. We’ve got a massive structural deficit, a transit system that needs a bailout, and a housing market that's feeling the squeeze. The City of Chicago Office of the Mayor is currently trying to balance being "progressive" with the cold, hard reality that the city needs businesses to stay.
They are trying to revitalize LaSalle Street—the very street they are located on—by turning old office buildings into apartments. This is a Mayor’s Office initiative. It requires tax breaks, zoning changes, and a lot of hand-holding. If it works, the Mayor’s Office looks like geniuses. If it fails, downtown becomes a ghost town.
Actionable Steps for Engaging with City Hall
If you want to understand or influence what’s happening in the Mayor's Office, don't just watch the news. The news gives you the "what," but you need the "how."
- Read the Budget Recommendations: Every October, the Mayor releases a massive book. Don't read the whole thing. Look at the "Executive Summary" and the "Departmental Highlights." It tells you exactly where the money is moving.
- Monitor the City Council Committees: The Mayor’s staff has to testify at committee meetings (like Finance or Public Safety). This is where they get grilled and where the real secrets come out. You can watch these live on the City Clerk’s website.
- Use the FOIA Portal: If you think something fishy is happening with a city contract, file a FOIA request specifically targeting the "Office of the Mayor." Be specific. "All emails between [Staff Member] and [Company] regarding [Project]."
- Engage with the Deputy Mayors: If you represent a community group or a business block, reach out to the specific Deputy Mayor’s office that handles your area. They are much more likely to respond than the general "Contact the Mayor" web form.
- Follow the Board of Ethics: The Mayor’s Office has to play by certain rules regarding gifts and lobbying. The Board of Ethics reports will show you who is "paying to play" or at least who is trying to.
The City of Chicago Office of the Mayor is a reflection of the city itself: loud, complicated, slightly dysfunctional, but incredibly powerful. Understanding how it operates is the first step to making sure it actually works for you, instead of just the people with the best lobbyists. It’s a grind, but in a city like Chicago, showing up is half the battle.