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The 39 largest Insurance companies in Chicago

Tamtam tracks 39 Insurance companies headquartered in Chicago. This list ranks all of them by number of employees on LinkedIn, led by HUB International, Bankers Life and CNA Insurance. Their median headcount is 202. Half of them were founded in 1992 or later.

๐Ÿ‡บ๐Ÿ‡ธ Chicago39 companiesUpdated Oct 9, 2026
#CompanyIndustryHeadquarters EmployeesFounded
1
HUB Internationalhubinternational.com

Advises businesses and individuals on insurance, risk management, employee benefits, retirement, and wealth management with tailored solutions.

Insurance ๐Ÿ‡บ๐Ÿ‡ธ Chicago 16,129 n/a
2
Bankers Lifecareersatbankerslife.com

The company provides insurance and investment solutions for middle-income Americans near or in retirement, with a focus on health and financial security

Insurance ๐Ÿ‡บ๐Ÿ‡ธ Chicago 11,377 1879
3
CNA Insurancecna.com

Provides commercial property and casualty insurance products and services for businesses and professionals across the U.S., Canada, and Europe.

Insurance ๐Ÿ‡บ๐Ÿ‡ธ Chicago 7,473 1897
4
Kemperkemper.com

Specialized insurer offering affordable personalized insurance solutions for individuals, families, and businesses through Auto and Life brands, serving over 49 million policies

Insurance ๐Ÿ‡บ๐Ÿ‡ธ Chicago 7,027 1990
5
Blue Cross Blue Shield Associationbcbs.com

Federation of independent Blue Cross and Blue Shield companies providing health care coverage and health insights for millions nationwide.

Insurance ๐Ÿ‡บ๐Ÿ‡ธ Chicago 5,630 1910
6
Combined, a Chubb Benefits Companycombinedinsurance.com

Provider of supplemental accident, health, and life insurance products focused on affordable, clear, and easy-to-understand coverage for families.

Insurance ๐Ÿ‡บ๐Ÿ‡ธ Chicago 5,177 1922
7
Ryan Specialtyryanspecialty.com

International specialty insurance firm providing underwriting, product development, administration, risk management, and wholesale brokerage services for brokers and carriers.

Insurance ๐Ÿ‡บ๐Ÿ‡ธ Chicago 4,562 2010
8
RT Specialtyrtspecialty.com

A leading wholesale distributor of specialty insurance products, providing expert risk modeling, market access, and claims advocacy for clients

Insurance ๐Ÿ‡บ๐Ÿ‡ธ Chicago 3,206 2010
9
Relation Insurance Servicesrelationinsurance.com

A trusted insurance partner that values relationships, listens to clients' needs, and provides practical solutions for personal and professional insurance decision-making

Insurance ๐Ÿ‡บ๐Ÿ‡ธ Chicago 898 2007
10
Ryan Specialty Underwriting Managersryanspecialty.com

RSG Underwriting Managers provides commercial insurance solutions through 21 MGUs for over 80 lines of business in unique market niches

Insurance ๐Ÿ‡บ๐Ÿ‡ธ Chicago 809 2010
11
Kin Insurancekin.com

A home insurance company utilizing vast property data to provide customized coverage at low prices through a user-friendly online platform

Insurance ๐Ÿ‡บ๐Ÿ‡ธ Chicago 707 2016
12
Independence Pet Groupindependencepetgroup.com

A leading provider of pet insurance and adoption software in North America, dedicated to strengthening the bond between pets and their owners

Insurance ๐Ÿ‡บ๐Ÿ‡ธ Chicago 706 n/a
13
Allied Benefit Systemsalliedbenefit.com

National healthcare solutions company specializing in customizing employer self-insurance benefits with innovative medical management strategies for better patient outcomes and cost control

Insurance ๐Ÿ‡บ๐Ÿ‡ธ Chicago 678 1980
14
Central States Funds/TeamCaremyteamcare.org

A non-profit labor health fund, providing quality, affordable healthcare to 500,000 members from 1,100 employers, with a commitment to exceptional service

Insurance ๐Ÿ‡บ๐Ÿ‡ธ Chicago 569 1950
15
The Warranty Groupassurant.com

Warranty services company merged with Assurant, focusing on enhancing capabilities and providing improved warranty solutions to clients.

Insurance ๐Ÿ‡บ๐Ÿ‡ธ Chicago 561 1964
16
Marble Boxmarblebox.com

Marble Box offers managed services for independent insurance agencies, focusing on functions such as policy checking, accounting, marketing, and sales management to enhance customer service

Insurance ๐Ÿ‡บ๐Ÿ‡ธ Chicago 453 2002
17
EquiTrust Life Insurance Companyequitrust.com

A national life insurance company offering competitive annuity products through independent agents, prioritizing integrity, customer service, and innovation

Insurance ๐Ÿ‡บ๐Ÿ‡ธ Chicago 421 2003
18
Society of Actuariessoa.org

A leading actuarial professional organization providing education, research, and credentials to empower actuaries to manage risk and provide expert advice

Insurance ๐Ÿ‡บ๐Ÿ‡ธ Chicago 354 1949
19
Renaissancerenaissanceins.com

Specializing in innovative technology and services, we help insurance agencies achieve organic and profitable growth

Insurance ๐Ÿ‡บ๐Ÿ‡ธ Chicago 255 2000
20
Honeycomb Insurancehoneycombinsurance.com

This company offers customized insurance policies for real estate properties using AI and computer vision, providing unbeatable rates with a transparent digital platform

Insurance ๐Ÿ‡บ๐Ÿ‡ธ Chicago 202 2019
21
HDI Global Insurance Companyhdi.global

A commercial property and casualty insurer providing insurance solutions to global clients, offering commercial insurance programs for US corporations

Insurance ๐Ÿ‡บ๐Ÿ‡ธ Chicago 186 1903
22
Old Republic Internationaloldrepublic.com

A Fortune 500 insurance business providing general and title insurance, risk management services, and specializing in decentralized operations with a focus on long-term trust and security

Insurance ๐Ÿ‡บ๐Ÿ‡ธ Chicago 186 1923
23
Vela Insurance Services (a Berkley Company)bit.ly

A leading insurance provider specializing in excess and surplus lines for small business, construction, specialty casualty, and professional liability markets nationwide

Insurance ๐Ÿ‡บ๐Ÿ‡ธ Chicago 184 1996
24
Clearcoverclearcover.com

Affordable car insurance with smart technology, fast claims, easy payments, and exceptional customer service Benefits include healthcare coverage, 401k contributions, and remote work options

Insurance ๐Ÿ‡บ๐Ÿ‡ธ Chicago 176 2016
25
Obieobieinsurance.com

An insurance technology solution for landlords, offering quick quotes and streamlined processes tailored for modern real estate investors

Insurance ๐Ÿ‡บ๐Ÿ‡ธ Chicago 173 2017
26
ISMIE Mutual Insurance Companyismie.com

A leading medical liability insurance provider in Illinois, offering nationwide coverage with a focus on protecting health care professionals and providing superior services

Insurance ๐Ÿ‡บ๐Ÿ‡ธ Chicago 165 1976
27
Tokio Marine Highlandtokiomarinehighland.com

A leading property and casualty underwriting agency specialized in private flood, fine art, real estate, and lender-placed insurance with industry-leading claims capabilities

Insurance ๐Ÿ‡บ๐Ÿ‡ธ Chicago 158 1962
28
ALASalas.com

A lawyer-owned mutual insurance company providing superior coverage, service, and risk management solutions for law firms worldwide

Insurance ๐Ÿ‡บ๐Ÿ‡ธ Chicago 157 1979
29
Berkley Select (a Berkley Company)berkleyselect.com

A prominent provider of professional liability insurance products for clients of various sizes and industries, offering coverage for complex needs

Insurance ๐Ÿ‡บ๐Ÿ‡ธ Chicago 143 1992
30
Old Republic General Insurance Grouporgig.com

Specializing in property and casualty insurance, the company offers specialized coverages for various industries, serving large corporations, small businesses, and consumers

Insurance ๐Ÿ‡บ๐Ÿ‡ธ Chicago 86 1923
31
Thompson Flanagannfp.com

An insurance brokerage firm dedicated to delivering superior results in a collegial environment fostering excellence, respect, teamwork, and integrity

Insurance ๐Ÿ‡บ๐Ÿ‡ธ Chicago 31 2004
32
Brokersโ€™ Risk, a subsidiary of One80 Intermediariesone80.com

A leading underwriter, intermediary, and broker specializing in innovative insurance solutions for alternative risk, public schools, and low income housing

Insurance ๐Ÿ‡บ๐Ÿ‡ธ Chicago 26 1979
33
Taos Global Group Inc.taosglobalgroup.com

A comprehensive financial services firm offering insurance, accounting, and investment services focused on saving money, tax planning, and wealth generation for clients

Insurance ๐Ÿ‡บ๐Ÿ‡ธ Chicago 23 2009
34
Bishop Street Underwriters

A company specializing in underwriting services and risk management solutions

Insurance ๐Ÿ‡บ๐Ÿ‡ธ Chicago 23 n/a
35
Alper Services, An Alera Group Companyaleragroup.com

An established insurance agency offering comprehensive risk management services, including workers' compensation, employee benefits, and various personal and commercial insurance coverage options

Insurance ๐Ÿ‡บ๐Ÿ‡ธ Chicago 22 1966
36
Lemme, a division of EPICepicbrokers.com

An experienced insurance and risk management division assisting professional service firms globally with integrated solutions, transparency, accountability, and proactive risk management

Insurance ๐Ÿ‡บ๐Ÿ‡ธ Chicago 17 1998
37
The Sandner Group, a subsidiary of One80 Intermediariesone80.com

A reinsurance intermediary providing innovative solutions for managing specialized risks through tailored coverages and alternative risk financing options

Insurance ๐Ÿ‡บ๐Ÿ‡ธ Chicago 17 2011
38
AGMI Insuranceagmiinsurance.com

Providing easy access to innovative solutions for commercial and specialized insurance needs

Insurance ๐Ÿ‡บ๐Ÿ‡ธ Chicago 13 n/a
39
AArdvark Insurance Agencyaardvarkchicago.com

Personalized insurance solutions saving money without compromising quality, with dedicated specialists offering best options at the best price for individual needs

Insurance ๐Ÿ‡บ๐Ÿ‡ธ Chicago 5 2009

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How this list is built

Every company on this list has a Tamtam company profile. The industry is the one the company gives on LinkedIn; categories such as SaaS or fintech are classified by Tamtam's AI from the company's website and LinkedIn page; and the headquarters city must match the company's own address. Companies are ranked by the number of employees on LinkedIn, and the list is refreshed every night. Classifications can be wrong, so treat the list as a starting point rather than an official ranking. Last updated Oct 9, 2026.

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