Company lists · Data refreshed October 2026

Top 25 Group health insurance agents based in Chicago, United States

Name: Group health insurance agents based in Chicago, United States
Creator: RevenueBase
License: https://creativecommons.org/licenses/by/4.0/

Compiled by the RevenueBase Data Team Data refreshed Oct 13, 2026 44 companies tracked

RevenueBase identified 44 company matches for group health insurance agents associated with Chicago, United States as of October 2026 and tracks 463 professional contacts across them, including 179 with verified work emails. Across the United States, Houston is the largest hub for this category (69 companies); Chicago has 44.

This list covers company matches for group health insurance agents associated with Chicago, United States, found by RevenueBase SmartSearch using the meaning of business descriptions in its company graph at Exact. Ranked by professionals tracked, largest first. Rows show recorded descriptions where available, Exact search membership and the snapshot date. Data refreshed October 13, 2026.

Published by RevenueBase, a B2B data infrastructure company. This list was built with RevenueBase SmartSearch, the natural-language company search RevenueBase customers use to build their own targeted lists and unlock verified emails and direct dials at the companies on them. How these lists are built and judged.

How to read this list RevenueBase SmartSearch · Exact Recorded Oct 13, 2026 How this list was built

44Companies

463Contacts tracked

179Verified emails

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The 25 largest group health insurance agents based in Chicago, United States

Ranked by team size

Top 25 of 44 company matches for group health insurance agents based in Chicago, United States, ordered by professional contacts tracked in RevenueBase, largest first. Recorded Oct 13, 2026. The RevenueBase SmartSearch column shows Exact match membership in this saved search. Click a contact count to view that company's people. Totals use company locations recorded by RevenueBase; the displayed preview is a smaller selection.
#	Company	RevenueBase SmartSearch	Headquarters	Employees	Contacts
1	Maestro Health	Exact match	Chicago, IL, United StatesHQ recorded Oct 13, 2026	201-500	66 contacts →
	Exact match “Maestro Health works with employers and their trusted advisors to administer self-funded health plans.” Recorded in the RevenueBase company graph · Oct 13, 2026 · View company records in RevenueBase
2	Flexible Benefit Service LLC Flex	Exact match	Chicago, IL, United StatesHQ recorded Oct 13, 2026	51-200	48 contacts →
	Exact match “Flexible Benefit Service LLC (Flex) is a leader in the health insurance and benefits administration markets.” Recorded in the RevenueBase company graph · Oct 13, 2026 · View company records in RevenueBase
3	Ryan Specialty Benefits	Exact match	Chicago, IL, United StatesHQ recorded Oct 13, 2026	51-200	44 contacts →
	Exact match “Ryan Specialty Benefits is a dynamic employee benefits service provider that delivers innovative solutions for its retail brokers and distribution trading partners for their…” Recorded in the RevenueBase company graph · Oct 13, 2026 · View company records in RevenueBase
4	Celtic Insurance Company	Exact match	Chicago, IL, United StatesHQ recorded Oct 13, 2026	n/a	41 contacts →
	Exact match “Celtic Insurance Company is a strong, committed, financially stable individual health insurance company specializing in quality individual health insurance.” Recorded in the RevenueBase company graph · Oct 13, 2026 · View company records in RevenueBase
5	OLD Republic Accident & Health	Exact match	Chicago, IL, United StatesHQ recorded Oct 13, 2026	n/a	29 contacts →
	Exact match “Old Republic Accident & Health provides accident and health insurance solutions to help employers, individuals, and families manage the financial burden of unexpected healthcare…” Recorded in the RevenueBase company graph · Oct 13, 2026 · View company records in RevenueBase
6	Evergreen Benefits Group	Exact match	Chicago, IL, United StatesHQ recorded Oct 13, 2026	1-10	28 contacts →
	Exact match “Evergreen Benefits Group is a full service insurance agency focusing on really great employee benefits.” Recorded in the RevenueBase company graph · Oct 13, 2026 · View company records in RevenueBase
7	Accurisk Solutions LLC	Exact match	Chicago, IL, United StatesHQ recorded Oct 13, 2026	51-200	25 contacts →
	Exact match “What happens when you combine innovative insurance products with outstanding customer service?” Recorded in the RevenueBase company graph · Oct 13, 2026 · View company records in RevenueBase
8	Metropolitan Insurance Group INC	Exact match	Chicago, IL, United StatesHQ recorded Oct 13, 2026	1-10	21 contacts →
	Exact match Recorded description not available. Recorded in the RevenueBase company graph · Oct 13, 2026 · View company records in RevenueBase
9	Ixsolutions	Exact match	Chicago, IL, United StatesHQ recorded Oct 13, 2026	11-50	20 contacts →
	Exact match “IXSolutions (IX) is a health insurance and benefits brokerage located in Chicago, Illinois.” Recorded in the RevenueBase company graph · Oct 13, 2026 · View company records in RevenueBase
10	Innotech Benefit Solutions	Exact match	Chicago, IL, United StatesHQ recorded Oct 13, 2026	201-500	18 contacts →
	Exact match “Innotech is a leading employee benefits enrollment and communication firm.” Recorded in the RevenueBase company graph · Oct 13, 2026 · View company records in RevenueBase
11	Enrollwell	Exact match	Chicago, IL, United StatesHQ recorded Oct 13, 2026	51-200	16 contacts →
	Exact match “We know benefits.” Recorded in the RevenueBase company graph · Oct 13, 2026 · View company records in RevenueBase
12	Alliant Employee Benefits Group Jan. 2011-Merged From Thesco & T&h Benefits	Exact match	Chicago, IL, United StatesHQ recorded Oct 13, 2026	1,001-5,000	12 contacts →
	Exact match “Employee Benefits consulting and brokerage specialists with extensive experience in program management, health and productivity strategies, compliance and communication services.” Recorded in the RevenueBase company graph · Oct 13, 2026 · View company records in RevenueBase
13	360 Benefits LLC	Exact match	Chicago, IL, United StatesHQ recorded Oct 13, 2026	11-50	10 contacts →
	Exact match “360 Benefits is a strategic partner of middle market companies helping to design employee benefit programs that control costs, guarantee compliance, and help recruit, retain, and…” Recorded in the RevenueBase company graph · Oct 13, 2026 · View company records in RevenueBase
14	Pahlke & Pahlke Insurance Agency, INC	Exact match	Chicago, IL, United StatesHQ recorded Oct 13, 2026	1-10	7 contacts →
	Exact match “For nearly three decades, Pahlke & Pahlke has worked with businesses, individuals, and families to put together sensible, cost-effective insurance and benefits planning strategies.” Recorded in the RevenueBase company graph · Oct 13, 2026 · View company records in RevenueBase
15	ASI Advanced Strategies INC	Exact match	Chicago, IL, United StatesHQ recorded Oct 13, 2026	1-10	5 contacts →
	Exact match “ASI is an employee benefits brokerage that works with small to mid-size companies to improve or create employee benefit packages.” Recorded in the RevenueBase company graph · Oct 13, 2026 · View company records in RevenueBase
16	Healthcare Solutions Team	Exact match	Chicago, IL, United StatesHQ recorded Oct 13, 2026	1-10	5 contacts →
	Exact match “We specialize in helping finding individuals, families, and small businesses find the right health insurance plan.” Recorded in the RevenueBase company graph · Oct 13, 2026 · View company records in RevenueBase
17	Hipskind Seyfarth Risk Solutions LLC	Exact match	Chicago, IL, United StatesHQ recorded Oct 13, 2026	1-10	4 contacts →
	Exact match “Hipskind Seyfarth Risk Solutions LLC is a full-service Brokerage and Consulting Firm.” Recorded in the RevenueBase company graph · Oct 13, 2026 · View company records in RevenueBase
18	Premier Financial Health Insurance	Exact match	Chicago, IL, United StatesHQ recorded Oct 13, 2026	1-10	4 contacts →
	Exact match “Premier Financial Insurance has grown to become one of the most popular and trusted providers of health insurance in Chicago, and throughout Illinois.” Recorded in the RevenueBase company graph · Oct 13, 2026 · View company records in RevenueBase
19	CS Insurance Strategies, A Marsh & Mclennan Agency LLC Company	Exact match	Chicago, IL, United StatesHQ recorded Oct 13, 2026	11-50	3 contacts →
	Exact match “CS Insurance Strategies, a Marsh & McLennan Agency LLC company, is a full-service brokerage helping clients navigate complicated risk and insurance issues.” Recorded in the RevenueBase company graph · Oct 13, 2026 · View company records in RevenueBase
20	HUB Insurance Agencies	Exact match	Chicago, IL, United StatesHQ recorded Oct 13, 2026	1-10	3 contacts →
	Exact match Recorded description not available. Recorded in the RevenueBase company graph · Oct 13, 2026 · View company records in RevenueBase
21	Endow, INC	Exact match	Chicago, IL, United StatesHQ recorded Oct 13, 2026	1-10	2 contacts →
	Exact match “Our History Endow was formed in 1978 by its principals, Thomas L.” Recorded in the RevenueBase company graph · Oct 13, 2026 · View company records in RevenueBase
22	Innovative Benefit Solutions	Exact match	Chicago, IL, United StatesHQ recorded Oct 13, 2026	1-10	2 contacts →
	Exact match “Innovative Benefit Solutions is a creative and forward-thinking benefits brokerage and consulting firm.” Recorded in the RevenueBase company graph · Oct 13, 2026 · View company records in RevenueBase
23	Rnfg Healthcare	Exact match	Chicago, IL, United StatesHQ recorded Oct 13, 2026	51-200	1 contacts →
	Exact match “This health benefits solution has a simple mission: to truly help employers make the BEST solution for their business, through strategically crafted benefit offerings.” Recorded in the RevenueBase company graph · Oct 13, 2026 · View company records in RevenueBase
24	MAS Health & Life	Exact match	Chicago, IL, United StatesHQ recorded Oct 13, 2026	11-50	1 contacts →
	Exact match “Customizing your coverage is essential as health insurance is not a “one size fits all” type of product.” Recorded in the RevenueBase company graph · Oct 13, 2026 · View company records in RevenueBase
25	Stumm Insurance, LLC	Exact match	Chicago, IL, United StatesHQ recorded Oct 13, 2026	11-50	1 contacts →
	Exact match Recorded description not available. Recorded in the RevenueBase company graph · Oct 13, 2026 · View company records in RevenueBase

RevenueBase SmartSearch

Describe a niche business in your own words. RevenueBase SmartSearch compares the meaning of your description with company business descriptions compiled in the RevenueBase company graph. Exact, Similar, Related and Broad control how closely companies must fit.

This list uses Exact for “group health insurance agents”. Each Exact match badge shows membership in that saved search; it is not an individual similarity score or a service-quality rating. Recorded descriptions are shown where available.

Showing 25 of 44 group health insurance agents based in Chicago, United States

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Group health insurance agents based in Chicago, United States at a glance

As of Oct 13, 2026

38.7%Verified-email coverage

10.5Average contacts per company

1-10Median size (employees)

Oct 13, 2026Page data refreshed

Companies by employee count

1-10

11-50

51-200

201-500

1,001-5,000

5,001-10,000

Email recency for this list is measured across the whole United States list rather than for Chicago, so it is reported there. Company counts and contact totals on this page are exact for Chicago, over 44 companies.

How this list was built

The recorded descriptions help you assess these company matches. Check a company’s website for its current services and locations.

Source: The RevenueBase company graph: 60 million companies and 398.9 million professional contacts resolved from primary sources, queried with RevenueBase SmartSearch, the natural-language company search available to every RevenueBase user.
What qualifies: Company records associated with Chicago, United States whose business descriptions match “group health insurance agents” by meaning at the Exact setting. Descriptions are compiled in the RevenueBase company graph from public websites, profiles and company information where available; they are not guaranteed quotations from the company's website.
RevenueBase SmartSearch: Describe a niche company in your own words to find businesses by meaning. Exact, Similar, Related and Broad control the breadth of RevenueBase SmartSearch. This saved list uses Exact. Each row's Exact match badge shows inclusion in that search, not an individual score or a service-quality judgment.
Public preview: The public preview omits records without a verified work email. Where headquarters information is recorded, preview rows are also filtered to this page’s location. Dataset totals and geographic summaries describe the full matched records before these preview filters.
Match quality: RevenueBase's August 25, 2026 study assessed 4,198 description/company pairs across matching settings. The publisher reports 86% good or better at Exact. This evaluates the method across queries; it does not audit this individual list. Recorded company descriptions, where available, help you judge each match yourself. Read the full methodology: how the lists are built and what the study measures.
Ranking: Team size, largest first: companies are ordered by the number of professionals RevenueBase tracks at each one. Employee ranges shown are reported bands, for context.
Verification: Every displayed company carries at least one verified work email. RevenueBase tracks 179 professional contacts with verified work emails across the full matched dataset. Contacts re-verify on a rolling cadence, and each contact's own verification date is shown inside RevenueBase.
Refresh: This page's figures were pulled from the company graph on October 13, 2026. Lists refresh periodically as the graph is re-checked.
Record context: Company records and descriptions can change. Check the company's website for its current services and locations.

Group health insurance agents by metro in the United States

Frequently asked

What is RevenueBase SmartSearch?

RevenueBase SmartSearch finds niche companies by the meaning of their business descriptions in the RevenueBase company graph. Exact, Similar, Related and Broad control how closely companies must fit your description. This list uses Exact for “group health insurance agents”; each Exact match badge shows search membership, not an individual similarity or quality score.

How many group health insurance agents are there based in Chicago, United States?

RevenueBase identified 44 company matches for group health insurance agents associated with Chicago, United States as of October 2026, using the meaning of business descriptions at Exact. This is the recorded matched set in the RevenueBase company graph.

What is the largest company on this list?

Maestro Health tops the displayed preview by professional contacts tracked in RevenueBase. Recorded headquarters appear in the company rows.

Which city in the United States has the most group health insurance agents?

Houston leads the United States with 69 company records, followed by New York (46) and Atlanta (44). Chicago has 44.

How do I get contact information for these companies?

A free RevenueBase account lets you run this exact search and work limited free results with 500 credits to start. Upgrading provides access to the 179 professional contacts with verified work emails tracked across these 44 companies; direct dials are available where recorded.

How current is this list?

The list refreshes periodically as the company graph is re-checked. This page's figures were pulled on October 13, 2026.

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About this data

RevenueBase is a B2B data infrastructure company. Its company graph covers 60 million companies and 398.9 million professional contacts, with emails verified on a rolling cadence rather than scraped once and left to decay. These company lists are generated directly from that graph with RevenueBase SmartSearch, the same natural-language company search every RevenueBase user has: describe a market in plain words, get the companies that match, and add verified emails and direct dials for the people at them. It is the same data that powers RevenueBase's B2B data products, and a free account includes 500 credits to start. How these lists are built and judged.