Who does ChatGPT name for roofing in Chicago, IL?

We wrote the six questions a buyer in Chicago, IL would type into an AI assistant when they need roofing work, asked each one on ChatGPT, Gemini, Perplexity with live web search, and wrote down every business the answers named. No opinions, no ranking of ours: this is what the assistants said on 2026-09-09.

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Trade: Roofing
Area: Chicago, IL
Questions: 6 asked, 6 answered
Engines: ChatGPT, Gemini, Perplexity
Date: 2026-09-09

Who came up most

Every business the answers named, counted across the six questions and the engines.

Champion Roofing Inc. (championroofing.com): named 4 times across Gemini, Perplexity
Green Attic Roofing (greenatticroofing.com): named 4 times across Gemini, Perplexity
Aegis Construction Group, Inc. (aegiscgi.com): named 3 times across ChatGPT, Gemini
Anchor Point Roofing (anchorpointroofing.com): named 3 times across ChatGPT, Gemini
Chicago Flat Roofing Contractors (chicagoflatroofingcontractors.org): named 3 times across ChatGPT, Gemini
Chicago Roofing Solutions (chicagoroofingsolution.com): named 3 times across ChatGPT, Gemini
Metalmaster Roofmaster (metalmaster-roofmaster.com): named 3 times across ChatGPT, Gemini, Perplexity
Reliable Roofing (reliable-roofing.com): named 3 times across Gemini, Perplexity

Directories and review sites the answers quoted: angi.com, thumbtack.com, reddit.com, youtube.com.

The six questions, answer by answer

The question a buyer would type, then what each assistant named.

01Who can repair a leaking roof in Chicago before the next rainstorm?

ChatGPT named: Qualified Roofing Services (chicagoqualifiedroofingservice.com), Chicago Flat Roofing Contractors (chicagoflatroofingcontractors.org), Chicago Roofing Solutions (chicagoroofingsolution.com).
Gemini named: Chicago Roofing Solutions, Champion Roofing, Leak Stop Roofing, Knickerbocker Roofing, Emergency Roofs.
Perplexity named: Allied Construction & Roofing (roof.alliedroofs.com), Patriot Roofing Chicago (patriotroofingchicago.com), Champion Roofing (championroofing.com), Emergency Roofs (emergencyroofs.com), Windward Roofing (windwardroofing.com).

02How much does it cost to replace an asphalt shingle roof on a house in Chicago?

ChatGPT named: Anchor Point Roofing (anchorpointroofing.com), GSKI Construction Group (gskiconstruction.com).
Gemini named: Shield Masonry & Roofing, Inc., Horizon Restoration, RX Roofing & Construction, Champion Roofing Inc., ASI Construction.
Perplexity named: Roof Replacement Chicago (roofreplacementchicago.com), GSKI Construction (gskiconstruction.com), Green Attic Roofing (greenatticroofing.com).

03Who repairs flat roofs on Chicago two-flats, especially where water pools after rain?

ChatGPT named: Anchor Point Roofing (anchorpointroofing.com), Aegis Construction Group (aegiscgi.com), Chicago Flat Roofing Contractors (chicagoflatroofingcontractors.org).
Gemini named: Aegis Construction Group, Inc., Chicago Flat Roofing Contractors, Anchor Point Roofing, Endurance Roofing Company, Midwest Pro Roofing & Tuckpointing.
Perplexity: no answer came back in time.

04Where can I find a roofer in Chicago to inspect hail damage and give me a written repair estimate?

ChatGPT named: Aegis Construction Group (aegiscgi.com), Taurus Roofing & Siding (taurusroofingandsiding.com).
Gemini named: Lakeland Exteriors, Green Attic Roofing, Dynasty Restoration Inc., A.B. Edward Enterprises, Inc., UAC 24-Hour.
Perplexity named: RX Roofing & Construction (rx-roof.com), Lindholm Chicago Roofing (lindholmroofing.com), Chicago Storm Pros (chicagostormpros.com), Advanced Roofing Team Construction (advancedroofingteam.com), PRQ Exteriors (prqexteriors.com).

05Which roofing contractors in Chicago install TPO roofing on commercial buildings?

ChatGPT named: Windward Roofing (windwardroofing.com), Showalter Roofing (showalterroofing.com), Great Lakes Roofing & Construction (greatlakesroof.com), Metalmaster Roofmaster (metalmaster-roofmaster.com), Conrad Roofing (conradroofing.com).
Gemini named: RMV Roofing, Metalmaster Roofmaster, Reliable Roofing, Great Lakes Roofing & Construction, Green Attic Roofing.
Perplexity named: Metalmaster Roofmaster (metalmaster-roofmaster.com), RMV Roofing (rmvroofing.com), Reliable Roofing (reliable-roofing.com), Windward Roofing (windwardroofing.com), Green Attic Roofing (greenatticroofing.com).

06Who can fix leaking chimney flashing and replace damaged shingles on a Chicago bungalow?

ChatGPT named: J&B Home Renovations (jandbhomerenovations.com), Gutter Wilson Roofing (gutterwilson.com).
Gemini named: Champion Roofing, Gutter Wilson, Reliable Roofing, M&M Home Remodeling Services, Chicago Roofing Solutions.
Perplexity named: Widen Chicago Chimney & Vent Co., Leaders Roofing, Chicago Fireplace Inc..

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If you are on this page and want it to stay that way, the Stay Named membership re-asks twelve questions every month. No one can promise what an AI assistant will say; what we deliver is the pages, the data and the listings that make being named possible, and the questions asked again so you see the change.

Dated read, not a ranking. Checked on 2026-09-09. How the assistants choose who to name, in plain words: the AI SEO guide. We ask the same six questions again and update this page; a business named today can be missing next time and the other way round. Next read: October 2026. Would rather walk through your own six answers with a person? Fifteen minutes, pick a time: book a call.