Selling
I Asked 3 AI Chatbots What 5 Chicago Homes Would Sell For. Here's How Close They Got (So Far)
I asked ChatGPT, Gemini and Claude to predict the final sale price of five Chicago homes under contract. The first home has closed. Here are all the guesses, the first result, and what it means for your home's value.
Everybody is asking AI what their home is worth. So I did too. After 25 years in real estate, I wanted to know: can a chatbot actually price a Chicago home, or is it just a very confident game show contestant?
The video above was made with AI. No robots were harmed, though one did guess "three goats."
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Round one: the chatbot that cheated (kind of)
On October 27, 2026, I picked five Chicago homes that had just closed and asked the chatbots what each one was worth.
Two of them never made it to the starting line. Copilot sent me to a sign-in page. Perplexity answered every question with "Sign up and repeat your request." Not exactly a home valuation.
ChatGPT did answer. But for three of the five homes, it searched the web, found the actual sale price, and handed it back as its "estimate." That's not a prediction, that's reading the answer key.
On the two homes where it couldn't find a sale yet, it leaned on the list price and the big website estimates. It guessed $640,000 on a 2-flat that sold for $625,000 and $550,000 on a Kenwood townhouse that sold for $540,000. Both homes sold under their list prices, and the chatbot guessed too high both times.
Lesson one: a chatbot is very good at finding numbers that are already online. That's not the same as knowing what your home will sell for.
Round two: no peeking allowed
So I made it fair. I picked five Chicago homes that were under contract, where the final price wasn't public yet, and asked ChatGPT, Gemini and Claude to predict each sale price. (I'm not sharing the addresses, out of respect for the buyers and sellers.)
Here's every guess:
| Home | List | ChatGPT | Gemini | Claude | Spread |
| Lake View townhouse | $625K | $630K | $620K | $620K | $10K |
| Norwood Park house | $390K | $425K | $402K | $400K | $25K |
| Jefferson Park 2-flat | $519.9K | $520K | $535K | $535K | $15K |
| Hyde Park condo | $460K | $455K | $455K | $450K | $5K |
| Garfield Ridge house | $349.9K | $375K | $370K | $355K | $20K |
"Spread" is the gap between the highest and lowest chatbot guess. K means thousand, so $625K is $625,000.
Notice something? Every single guess lands within about 10% of the list price. The chatbots aren't really pricing the house. They're starting from the asking price and nudging it up or down based on how fast the home went under contract.
The first result is in
The Lake View townhouse closed on October 29, 2026, for $635,000, which is $10,000 over its $625,000 list price, according to its public sold record on Realtor.com.
- ChatGPT guessed $630,000: off by $5,000
- Gemini guessed $620,000: off by $15,000
- Claude guessed $620,000: off by $15,000
All three guessed low. ChatGPT gets the early lead. Honestly, though, any of these guesses would be fine for dinner-table conversation. It's one home, and the other four haven't closed yet. I'll update the scoreboard as they do.
Why the AI guesses bounce around
- They only know what's online. List price, listing photos, and whatever estimate pages they happen to find. Different pages, different answers.
- They anchor on the asking price. In round one, when the list price was too high, the chatbot's guess was too high too.
- They can't walk through the house. They can't smell the basement, see the 1970s bathroom, or notice the new roof isn't actually new.
- They don't know the negotiation. Multiple offers, an inspection credit, a seller who needs to move by Friday. That's where the final price is really made.
What a real price opinion looks like
When I price a home, I start with a comparative market analysis (CMA). That means recent closed sales of similar homes nearby, adjusted for size, condition, updates, parking and outdoor space. Then I look at what's competing right now: active listings, what's gone under contract, and how fast. Then I walk through the home, because the details that move the price by $20,000 rarely show up in an online listing.
When to use AI, and when to call me
Use AI for a quick ballpark, to learn the lingo, or to make a list of questions. I use it every day in my business, and I teach other people how to use it at my AI studio.
Call an agent when real money is on the line: setting a list price, writing an offer, or deciding whether to sell this spring or wait. A $15,000 miss is a funny story on a blog. It's not funny on your closing statement.
Thinking about selling and want a real number? I offer full-service real estate for a 1% commission. Call or text me at 312.882.9797.
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