Insurance brokers in Chicago that AI assistants recommend

Name: AI assistant recommendations: Insurance brokers in Chicago, November 2026
Creator: AIGROW
License: https://creativecommons.org/licenses/by/4.0/

Mesirow is named most, in 58% of 36 answers.

The ranking

AI Recommendation Rate

1Mesirow58%
95%: 42 to 73%
ChatGPT
83%
Claude
42%
Gemini
50%
Questions
4 of 4
Avg. position
1.8
Named in answers to
- Who is the best insurance broker in Chicago?, from ChatGPT, Claude and Gemini
- I need insurance for my small business in Chicago. Which broker would you recommend?, from ChatGPT, Claude and Gemini
- Which insurance agency in Chicago can find me cheaper home and car insurance?, from ChatGPT
- Which independent insurance broker in Chicago would you recommend to a family?, from ChatGPT
Also written Mesirow Insurance Services, Mesirow Financial
Is this your business?
2The Horton Group44%
95%: 30 to 60%
ChatGPT
42%
Claude
67%
Gemini
25%
Questions
4 of 4
Avg. position
3.4
Named in answers to
- Who is the best insurance broker in Chicago?, from ChatGPT and Claude
- I need insurance for my small business in Chicago. Which broker would you recommend?, from ChatGPT and Claude
- Which insurance agency in Chicago can find me cheaper home and car insurance?, from ChatGPT and Gemini
- Which independent insurance broker in Chicago would you recommend to a family?, from Claude and Gemini
Also written Horton Group
Is this your business?
3HUB International42%
95%: 27 to 58%
ChatGPT
83%
Claude
17%
Gemini
25%
Questions
4 of 4
Avg. position
1.9
Named in answers to
- Who is the best insurance broker in Chicago?, from ChatGPT, Claude and Gemini
- I need insurance for my small business in Chicago. Which broker would you recommend?, from ChatGPT, Claude and Gemini
- Which insurance agency in Chicago can find me cheaper home and car insurance?, from ChatGPT
- Which independent insurance broker in Chicago would you recommend to a family?, from ChatGPT
Also written Hub International
Is this your business?
4Gold Coast Insurance Group22%
95%: 12 to 38%
ChatGPT
0%
Claude
67%
Gemini
0%
Questions
4 of 4
Avg. position
1.4
Named in answers to
- Who is the best insurance broker in Chicago?, from Claude
- I need insurance for my small business in Chicago. Which broker would you recommend?, from Claude
- Which insurance agency in Chicago can find me cheaper home and car insurance?, from Claude
- Which independent insurance broker in Chicago would you recommend to a family?, from Claude
Is this your business?
5Assurance19%
95%: 10 to 35%
ChatGPT
25%
Claude
25%
Gemini
8%
Questions
2 of 4
Avg. position
3.3
Named in answers to
- Who is the best insurance broker in Chicago?, from ChatGPT and Claude
- I need insurance for my small business in Chicago. Which broker would you recommend?, from ChatGPT and Gemini
Also written Assurance Agency, Assurance, a Marsh & McLennan Agency company, Assurance, a Marsh & McLennan Agency LLC company
Is this your business?
6Hylant14%
95%: 6 to 29%
ChatGPT
0%
Claude
0%
Gemini
42%
Questions
3 of 4
Avg. position
2
Named in answers to
- Who is the best insurance broker in Chicago?, from Gemini
- I need insurance for my small business in Chicago. Which broker would you recommend?, from Gemini
- Which independent insurance broker in Chicago would you recommend to a family?, from Gemini
Is this your business?
7Greater Chicago Insurance Agency11%
95%: 4 to 25%
ChatGPT
0%
Claude
0%
Gemini
33%
Questions
2 of 4
Avg. position
1.5
Named in answers to
- Which insurance agency in Chicago can find me cheaper home and car insurance?, from Gemini
- Which independent insurance broker in Chicago would you recommend to a family?, from Gemini
Is this your business?
8Arthur J. Gallagher & Co.11%
95%: 4 to 25%
ChatGPT
0%
Claude
33%
Gemini
0%
Questions
2 of 4
Avg. position
3
Named in answers to
- Who is the best insurance broker in Chicago?, from Claude
- I need insurance for my small business in Chicago. Which broker would you recommend?, from Claude
Also written Gallagher
Is this your business?
9Goosehead Insurance11%
95%: 4 to 25%
ChatGPT
8%
Claude
25%
Gemini
0%
Questions
1 of 4
Avg. position
3
Named in answers to
- Which insurance agency in Chicago can find me cheaper home and car insurance?, from ChatGPT and Claude
Also written Goosehead Insurance - Chicago
Is this your business?
10Insure on the Spot8%
95%: 3 to 22%
ChatGPT
25%
Claude
0%
Gemini
0%
Questions
1 of 4
Avg. position
1
Named in answers to
- Which insurance agency in Chicago can find me cheaper home and car insurance?, from ChatGPT
Is this your business?
11InsureOne8%
95%: 3 to 22%
ChatGPT
0%
Claude
0%
Gemini
25%
Questions
1 of 4
Avg. position
1.3
Named in answers to
- Which insurance agency in Chicago can find me cheaper home and car insurance?, from Gemini
Also written InsureOne Insurance Agency
Is this your business?
12Associated Agencies, Inc.8%
95%: 3 to 22%
ChatGPT
0%
Claude
0%
Gemini
25%
Questions
2 of 4
Avg. position
2.3
Named in answers to
- Who is the best insurance broker in Chicago?, from Gemini
- Which independent insurance broker in Chicago would you recommend to a family?, from Gemini
Is this your business?
13AssuredPartners8%
95%: 3 to 22%
ChatGPT
0%
Claude
8%
Gemini
17%
Questions
2 of 4
Avg. position
4
Named in answers to
- Who is the best insurance broker in Chicago?, from Gemini
- I need insurance for my small business in Chicago. Which broker would you recommend?, from Claude and Gemini
Also written AssuredPartners Chicago
Is this your business?
14Insureon8%
95%: 3 to 22%
ChatGPT
17%
Claude
8%
Gemini
0%
Questions
1 of 4
Avg. position
4.3
Named in answers to
- I need insurance for my small business in Chicago. Which broker would you recommend?, from ChatGPT and Claude
Is this your business?
15Acceptance Insurance6%
95%: 2 to 18%
ChatGPT
0%
Claude
17%
Gemini
0%
Questions
1 of 4
Avg. position
1.5
Named in answers to
- Which insurance agency in Chicago can find me cheaper home and car insurance?, from Claude
Also written Acceptance Insurance Agency
Is this your business?
16Insure Chicago6%
95%: 2 to 18%
ChatGPT
0%
Claude
17%
Gemini
0%
Questions
2 of 4
Avg. position
2.5
Named in answers to
- I need insurance for my small business in Chicago. Which broker would you recommend?, from Claude
- Which insurance agency in Chicago can find me cheaper home and car insurance?, from Claude
Is this your business?
17Acrisure6%
95%: 2 to 18%
ChatGPT
0%
Claude
17%
Gemini
0%
Questions
1 of 4
Avg. position
4.5
Named in answers to
- I need insurance for my small business in Chicago. Which broker would you recommend?, from Claude
Also written Acrisure Chicago
Is this your business?

Open a row to see each assistant's share of its own answers. Questions counts how many of the four produced the name at least once; position is where it came in the answer's list, 1 being first. 33 more names came up in a single answer and are counted above but not listed.

Insurance brokers in Chicago: is this your field?

50different names in 36 answers, 33 of them only once. The assistants change their minds from one answer to the next.

Check whether AI names you

Is this your business?

Named on this list? Get the badge for your website and a free scan of who AI assistants recommend to your customers. Use the badge only for a business named here. It records this edition, without verifying ownership or promising future mentions.

AIGROW ScoreIs this your business? See your AIGROW ScoreHow the AIGROW Score is measured

No business can pay to appear in the Index, rise in it or be removed from it. How the Index stays neutral

AI Visibility Index · November 2026

Asked about insurance brokers in Chicago, ChatGPT, Claude and Gemini named Mesirow most often, in 58% of answers (its AI Recommendation Rate), then The Horton Group (44%) and HUB International (42%). Across 36 answers they named 50 different businesses, 33 of them only once. Each of four buyer questions was asked three times, in English, in November 2026.

The AI Recommendation Rate is the fraction of the 36 answers that named a business. The range under it is a 95% confidence interval: where two ranges overlap, the gap between those businesses could be chance.

Names are printed as the assistants wrote them. We have not checked that any of them is good, open, or real.

58% of answers named Mesirow

Answers: 36
Businesses named: 50
Named only once: 33
Named by 2+ assistants: 7 of 17
Named again on a rerun: 46%

Edition November 2026. Download the data

What each assistant said

The same questions, the same number of times, and often different names. Each column is one assistant's top five from the ranking above, with the share of its own answers that named them.

#	ChatGPT	Claude	Gemini
1	Mesirow83%	The Horton Group67%	Mesirow50%
2	HUB International83%	Gold Coast Insurance Group67%	Hylant42%
3	The Horton Group42%	Mesirow42%	Greater Chicago Insurance Agency33%
4	Assurance25%	Arthur J. Gallagher & Co.33%	The Horton Group25%
5	Insure on the Spot25%	Assurance25%	HUB International25%

Questions about insurance brokers in Chicago

How AI assistants recommend insurance brokers

ChatGPT, Claude and Gemini named Mesirow most often, in 58% of 36 answers, then The Horton Group (44%) and HUB International (42%). The names come from what the assistants answered to four buyer questions in November 2026; we have not checked that any of them is good, open or real.

Not always. ChatGPT named Mesirow most often (83% of its answers), Claude The Horton Group (67%) and Gemini Mesirow (50%). 7 of the 17 listed businesses were named by two or more of them.

Each question was asked three times. Of the names an assistant gave for a question, 46% came back in two or more of those runs; the rest came up once. The 95% range beside each rate in the ranking shows how far it could move by chance.

Run the free checker: it asks ChatGPT, Claude, Gemini and Grok two of the Index questions for insurance brokers, with the category and the place already filled in, and shows every answer word for word. About 30 seconds, no sign-up. The page on how AI assistants recommend insurance brokers shows what an owner can work on. Nothing can guarantee that an assistant names you.

Named here? Put it on your site

Every business in the ranking was named in two or more answers. The badge says that and nothing more: no position, because the ranges above do not support one. It links back to this page, so anyone can check.

Correct or remove a listing

<a href="https://aigrow.gg/index/insurance-brokers/chicago"><img src="https://aigrow.gg/badges/index/2026-11/insurance-brokers/chicago.svg" width="312" height="100" alt="Named by AI assistants: Insurance brokers in Chicago, AIGROW AI Visibility Index, November 2026"></a>

The questions

Asked word for word, three times each, to every assistant. The prompt is the one the free scan uses. No web search, no location and no chat history, so every answer starts from the same place.

1Who is the best insurance broker in Chicago?
2I need insurance for my small business in Chicago. Which broker would you recommend?
3Which insurance agency in Chicago can find me cheaper home and car insurance?
4Which independent insurance broker in Chicago would you recommend to a family?

How to read this page

The full method

What it measures: Which names these models produce when asked cold, from what they learned in training. It is not a review, a rating or our recommendation, and a business missing here may simply be one the models were never shown.
Why the ranges matter: 36 answers is a sample. Asked again next month, most shares will move by a few points; the ranges say how far they could move by chance alone.
One business, several spellings: Branches, legal suffixes and spellings of one business are merged, and the other spellings are printed under its name. Names that might be two businesses are kept apart.
A name is wrong: If a business here is closed, misnamed or yours and you want it removed, tell us. We correct or remove it when the page is next published.

Where the assistants look

The sites read most often, with web search on, before the assistants answer about this category in the United States. From the AI Source Map: 11 answers.

See every site for this category