> Enrich.chat gives AI agents verified work emails and mobiles. To use it from an agent, read https://enrich.chat/agents.md . This is the Markdown version of https://enrich.chat/companies-in/chicago-il/insurance/ # Insurance Companies in Chicago, IL The bigger insurance companies headquartered in Chicago, IL, with what they do, their sizes and how to reach their people. By Enrich.chat Editorial. Updated October 22, 2026. **Short answer:** Among the insurance companies counted in Chicago, IL, the biggest by headcount range include Old Republic Specialty Insurance Group, Cna Insurance and Combined, A Chubb Benefits. They are mostly very small: 62% have 50 or fewer employees. ## Which insurance companies are in Chicago? Among the companies whose public profile lists Insurance as their industry and Chicago, IL as their headquarters, the biggest by headcount range include Old Republic Specialty Insurance Group, Cna Insurance, Combined, A Chubb Benefits, Ryan Specialty and Bankers Life. Names link to a company profile where we have one. | Company | Employees | | --- | --- | | Old Republic Specialty Insurance Group | 10,001+ | | Cna Insurance | 5,001 to 10,000 | | Combined, A Chubb Benefits | 5,001 to 10,000 | | Ryan Specialty | 5,001 to 10,000 | | Bankers Life | 1,001 to 5,000 | | Rt Specialty | 1,001 to 5,000 | | United Benefit Advisors Uba | 1,001 to 5,000 | | Wholesure | 1,001 to 5,000 | | Independence Pet Group | 501 to 1,000 | | Allied Benefit Systems | 501 to 1,000 | | Equitrust Life Insurance | 501 to 1,000 | | Marble Box | 501 to 1,000 | | Spg - Specialty Program Group | 501 to 1,000 | | Central States Funds Teamcare | 501 to 1,000 | | Peak6 Insurtech | 501 to 1,000 | | Clearcover | 201 to 500 | | Onedigital Advanced Health | 201 to 500 | | Tokio Marine Highland | 201 to 500 | | Old Republic Inland Marine | 201 to 500 | | Superior Insurance Partners | 201 to 500 | | Repair Ventures | 201 to 500 | | Lifequotes.Com | 51 to 200 | | Renaissance | 51 to 200 | | Rising Medical Solutions | 51 to 200 | | Honeycomb Insurance | 51 to 200 | The table shows the 25 biggest by headcount range, with ties broken by audience size. The charts and percentages below cover every company counted for this page, not just these 25, and companies with fewer than 11 employees are not counted. Headquarters is the location on each company's public profile. ## What do insurance companies in Chicago do? Insurance is a broad label. The most common NAICS codes among them are 524210 (59%), 523940 (3%) and 524113 (3%). **Figure: What insurance companies in Chicago do.** Bars for the share of counted insurance companies with each code: 524210 59%, 523940 3%, 524113 3%, 524128 3%, 524292 3%, 541110 3%, 541191 3%. *Share of counted insurance companies in Chicago by their NAICS code.* [NAICS 524210](https://enrich.chat/naics/524210/)[NAICS 523940](https://enrich.chat/naics/523940/)[NAICS 524113](https://enrich.chat/naics/524113/)[NAICS 524128](https://enrich.chat/naics/524128/)[NAICS 541110](https://enrich.chat/naics/541110/)[NAICS 541191](https://enrich.chat/naics/541191/) ## How big are they? 62% of the insurance companies counted in Chicago have 50 or fewer employees, and the middle one is in the 11 to 50 range. Companies with fewer than 11 employees are not counted. **Figure: Size of insurance companies in Chicago.** Seven columns for the share of counted insurance companies in Chicago in each employee range: 11 to 50 62%, 51 to 200 22%, 201 to 500 4%, 501 to 1,000 5%, 1,001 to 5,000 3%, 5,001 to 10,000 2%, 10,001+ 1%. *Share of counted insurance companies in Chicago in each employee range.* ## How old are they? Most were founded in the 2010s (26%), then the 2000s (19%). **Figure: When insurance companies in Chicago were founded.** Eight columns for the share of counted insurance companies in Chicago founded in each era: Before 1960 13%, 1960s 6%, 1970s 5%, 1980s 9%, 1990s 11%, 2000s 19%, 2010s 26%, 2020s 12%. *Share of counted insurance companies in Chicago by the era they were founded in, for the ones that list a founding year.* ## How insurance companies compare - 62% of insurance companies in Chicago have 50 or fewer employees, against 71% across other cities on this site. - 38% were founded in 2010 or later, against 54% across other cities on this site. ## How do you reach the people at insurance companies in Chicago? The people to talk to are usually operations, claims and technology leaders. Build the list in three prompts to your AI agent. ### 1. Count them (free) Counting who matches never uses credits. ```text Use www.enrich.chat to count the insurance companies in Chicago, IL ``` ### 2. Find the people (5 credits per person) Name the roles you sell to. Each person returned is 5 credits, and name, title and company are included. ```text Use www.enrich.chat to find the operations, claims and technology leaders at insurance companies in Chicago, IL, with their titles ``` ### 3. Get their work emails (10 credits each) An email is 10 credits only when one is found. Every email comes with a status: verified, catch-all or unknown. ```text Use www.enrich.chat to find the work emails for these people and tell me which ones are verified ``` ## More to explore Other industries in Chicago: [Real Estate Companies](https://enrich.chat/companies-in/chicago-il/real-estate/)[IT Services Companies](https://enrich.chat/companies-in/chicago-il/it-services-and-it-consulting/)[Financial Services Companies](https://enrich.chat/companies-in/chicago-il/financial-services/)[Advertising Agencies](https://enrich.chat/companies-in/chicago-il/advertising-services/)[Software Companies](https://enrich.chat/companies-in/chicago-il/software-development/)[Construction Companies](https://enrich.chat/companies-in/chicago-il/construction/)[Hospitals and Health Care Organizations](https://enrich.chat/companies-in/chicago-il/hospitals-and-health-care/)[Consulting Firms](https://enrich.chat/companies-in/chicago-il/business-consulting-and-services/)[Nonprofit Organizations](https://enrich.chat/companies-in/chicago-il/non-profit-organizations/)[Law Firms](https://enrich.chat/companies-in/chicago-il/law-practice/)[Technology and Internet Companies](https://enrich.chat/companies-in/chicago-il/technology-information-and-internet/)[Staffing and Recruiting Firms](https://enrich.chat/companies-in/chicago-il/staffing-and-recruiting/)[Legal Services Firms](https://enrich.chat/companies-in/chicago-il/legal-services/)[Education Organizations](https://enrich.chat/companies-in/chicago-il/education-administration-programs/)[Logistics and Supply Chain Companies](https://enrich.chat/companies-in/chicago-il/transportation-logistics-supply-chain-and-storage/)[Colleges and Universities](https://enrich.chat/companies-in/chicago-il/higher-education/)[Architecture Firms](https://enrich.chat/companies-in/chicago-il/architecture-and-planning/)[Manufacturers](https://enrich.chat/companies-in/chicago-il/manufacturing/)[Food and Beverage Manufacturers](https://enrich.chat/companies-in/chicago-il/food-and-beverage-manufacturing/)[All of Chicago](https://enrich.chat/companies-in/chicago-il/) Insurance Companies in other cities: [Houston, TX](https://enrich.chat/companies-in/houston-tx/insurance/)[Miami, FL](https://enrich.chat/companies-in/miami-fl/insurance/)[Dallas, TX](https://enrich.chat/companies-in/dallas-tx/insurance/)[Atlanta, GA](https://enrich.chat/companies-in/atlanta-ga/insurance/)[Tampa, FL](https://enrich.chat/companies-in/tampa-fl/insurance/)[Austin, TX](https://enrich.chat/companies-in/austin-tx/insurance/)[San Diego, CA](https://enrich.chat/companies-in/san-diego-ca/insurance/)[Phoenix, AZ](https://enrich.chat/companies-in/phoenix-az/insurance/)[San Antonio, TX](https://enrich.chat/companies-in/san-antonio-tx/insurance/)[Charlotte, NC](https://enrich.chat/companies-in/charlotte-nc/insurance/) ## Frequently asked questions ### Which are the biggest insurance companies in Chicago? Among those counted, they include Old Republic Specialty Insurance Group, Cna Insurance, Combined, A Chubb Benefits, Ryan Specialty and Bankers Life, ranked by headcount range. ### How big are insurance companies in Chicago? 62% of those counted have 50 or fewer employees, and the middle one is in the 11 to 50 range. Companies with fewer than 11 employees are not counted. ### Which companies count as insurance? Companies whose public profile lists Insurance as their industry and whose headquarters are in Chicago, IL. ## Try this prompt Find the people at insurance companies in Chicago ```text Use www.enrich.chat to find the operations, claims and technology leaders at insurance companies in Chicago, IL, with titles and verified work emails ``` ## Related - [Companies using a technology](https://enrich.chat/companies-using/) - [Real Estate Companies in Chicago](https://enrich.chat/companies-in/chicago-il/real-estate/) - [IT Services Companies in Chicago](https://enrich.chat/companies-in/chicago-il/it-services-and-it-consulting/) - [Financial Services Companies in Chicago](https://enrich.chat/companies-in/chicago-il/financial-services/) - [Advertising Agencies in Chicago](https://enrich.chat/companies-in/chicago-il/advertising-services/) - [Insurance Companies in Houston](https://enrich.chat/companies-in/houston-tx/insurance/) - [Insurance Companies in Miami](https://enrich.chat/companies-in/miami-fl/insurance/) - [Insurance Companies in Dallas](https://enrich.chat/companies-in/dallas-tx/insurance/) - [Insurance Companies in Atlanta](https://enrich.chat/companies-in/atlanta-ga/insurance/) - [Tech stack lookup](https://enrich.chat/tools/tech-stack-lookup/)