We Asked AI For The Best Lawyer In Chicago. Here's Who It Named.
TL;DR Ask AI for the best lawyer in Chicago and a few names do most of the work, like Schiller DuCanto & Fleck in divorce and Clifford Law Offices in malpractice. We ran thousands of Chicago queries through four AI tools, and in some practice areas just three firms took half the answers.
A Chicago couple decides to split up. Before either of them calls a lawyer, one of them asks ChatGPT who the best divorce firm in the city is.
Three names come back. The list is short, and it’s close to the same short list every time.
We know, because we asked, thousands of times, across every practice area in Chicago, on four different AI tools.
Why This Is A Different Game
Google was a ranking engine. It gave a searcher ten links and let them choose. The AI tools are recommendation engines. They choose first, hand over three names, and skip the rest.
In Chicago, that shift has teeth, because the answers crowd hard around a few firms.
What AI Says About Chicago Lawyers
We read 2,224 clean Chicago answers across 25 practice areas.
Some fields are nearly locked. In Chicago divorce, three firms took close to half of every answer: Schiller DuCanto & Fleck, Beermann, and Berger Schatz.
In medical malpractice, it was Clifford Law Offices, Salvi, Schostok & Pritchard, and Levin & Perconti, again about half between the three of them.
In business law, Kirkland & Ellis and Sidley Austin alone split most of the room.
Across practice areas, the top 3 Chicago firms averaged about 38% of all the names, a touch tighter than most cities we studied.
Behind them, roughly 59 firms per practice area, most mentioned once.
One Chicago wrinkle: the tools leaned a little less on directories here than elsewhere.
Perplexity cited a directory in 87% of its Chicago answers, lower than most markets, and pointed at firms’ own sites more often.
Super Lawyers (14.2%) and Justia (12%) still led its sources, with Best Law Firms close behind.
And the tools still didn’t agree with each other. ChatGPT and Perplexity overlapped about 7% on which Chicago firms they named. Gemini named a firm in only about 3% of its answers.
Being Named Isn't Being The Best
This measures who AI mentions, not who wins. A firm with strong profiles will out-appear a stronger firm the machines can’t see. If a weaker Chicago competitor keeps surfacing and you don’t, recognition is the gap, and recognition is fixable.
How To Show Up In Chicago's AI Results
Run the four tools for your practice area in Chicago and note who gets named and which sites get cited. Get your firm onto those sources, starting with Super Lawyers and Justia.
Since Chicago answers point at firm websites more than most markets do, make sure your own pages say plainly what you do and where you do it. Keep your firm’s details identical everywhere. Then check all four tools, because they each crown a different list.
The Question That Matters
Tonight a Chicagoan will ask AI to name a lawyer. Three names, no page two.
The only question is whether yours is one of them.
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