After nearly 30 years in Chicago real estate and more than 400 families helped, I’ve noticed something. The questions people are afraid to ask their agent are almost always the most important ones. So I answered them — all of them — in one place.
Real estate is one of the most significant financial and emotional decisions most people will ever make. And yet most of the information out there is either buried in jargon, written for industry insiders, or designed to get you to click rather than actually understand what’s happening.
That’s why I built the Chicago Real Estate FAQ — a free resource with more than 70 questions and answers, organized by situation, written the way I’d explain things sitting across from you at a kitchen table.
Why Chicago Is Different From Every Other Market
If you’ve bought or sold real estate in another state, you may be surprised by how Chicago works. A few things that catch people off guard every single time:
These aren’t obscure technicalities. They’re the rules of the market. And the buyers and sellers who understand them before they start are the ones who make decisions with confidence — rather than reacting to surprises.
The FAQ Is Organized by Your Situation — Not by Topic
Most real estate guides are organized the way agents think about the process. This one is organized the way people actually experience it — by where they are in their life right now.
When you visit the FAQ, you’ll find nine sections. Just find the one that sounds most like you:
- I’ve Never Bought a Home Before — the basics, explained from scratch. What is pre-approval? What is earnest money? What happens at closing?
- Moving to Chicago for the First Time — what makes this market different, how to think about neighborhoods, what relocators wish they’d known.
- Moving from the Suburbs into the City — what changes, what doesn’t, and what to watch for with parking, taxes, and condo buildings.
- I Own a Home and Want a Bigger One — the sell-first vs. buy-first question, how equity works, what actually adds value before you list.
- I’m Ready to Sell — pricing strategy, staging, timing, what the inspection process really means, and what selling actually costs.
- I Want to Downsize or Simplify — how to know when the timing is right, how to handle the emotional side, what the options actually look like.
- Moving Out of Chicago or Illinois — how to sell remotely, how to find a trusted agent in your new city, what your net proceeds will look like.
- Helping a Parent or Family Member — how to be involved without overstepping, what to know about senior transitions, how to help a first-time buyer.
- Who Is Maureen? Who Is @properties Christie’s? — because you should know who’s answering these questions before you decide whether to trust them.
A Few More Questions the FAQ Answers Directly
Read the Full Chicago Real Estate FAQ
70+ questions. 9 sections. Plain English. No obligation, no sales pitch — just the answers you actually need.
Go to the FAQ →Why I Built This
I’ve been a REALTOR® since 1995. In that time I’ve noticed that the people who feel most confident in a real estate transaction aren’t necessarily the ones with the most money or the most experience. They’re the ones who took time to understand the process before they were in the middle of it.
That’s something I learned as a teacher, before I got into real estate: knowledge doesn’t just inform decisions. It changes how people experience the process. A buyer who understands what earnest money is, why Illinois requires an attorney, and how the tax proration works at closing isn’t just better prepared — they’re calmer, more decisive, and less likely to make moves they regret.
The FAQ is my attempt to give every person who’s thinking about buying or selling in Chicago — at any stage, in any situation — the same level of understanding I’d give to a close friend sitting across from me. No jargon. No pressure. Just clear, honest answers.
If you have questions that aren’t covered, or if something you read raises a new question, reach out. That’s what I’m here for.
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