LGBTQ+ Friendly Insurance Agents in Chicago

Karen Ayers

State Farm Insurance (Karen Ayers Agency)

1428 W Irving Park Rd, Chicago, IL 60613

Karen Ayers has run her State Farm agency on West Irving Park Road, near Chicago's Lakeview and Boystown neighborhoods, since becoming an agent in 2001. On her own site, Ayers describes herself as a longtime member of the LGBT Chamber of Commerce and the Uptown Chamber of Commerce, and notes she has worked with local block clubs over the years. Her team of licensed insurance professionals writes auto, home, and life insurance, among other lines, for clients across Chicago, Uptown, Lakeview, Andersonville, and nearby suburbs. Ayers's inclusion here reflects her stated chamber membership rather than a broader ownership or ally claim.

David Frederickson

State Farm Insurance David J. Frederickson Agency Inc

6255 N Clark St, Chicago, IL 60660

Dave Frederickson has run the David J. Frederickson Agency, a State Farm agency, from North Clark Street in Chicago's Edgewater neighborhood near Andersonville, since starting the business in September 1996. On his own site, Frederickson lists board membership on the Edgewater Chamber of Commerce and membership in the Andersonville, Uptown, and Chicago Gay and Lesbian Chambers, as well as the Rogers Park Business Alliance. The agency writes auto, home, and life insurance for Chicago-area clients, and self-reports a 4.9 rating across 595 reviews on its own site (not independently verified). Frederickson's inclusion here reflects longstanding chamber membership rather than a stated LGBTQ+ ownership or ally claim.

Lamont Robinson

Robinson & Associates Insurance (Allstate)

5050 S Indiana Ave, Chicago, IL 60615

Lamont Robinson has owned Robinson & Associates Insurance, an Allstate agency, since 2007. Robinson is openly gay — Wikipedia identifies him as the first openly LGBTQ African American to serve in the Illinois legislature, where he represented the 5th District in the Illinois House from 2019 to 2023. He now serves as 4th Ward Alderman on the Chicago City Council. The agency is a member of the LGBT Chamber of Commerce of Illinois. Robinson & Associates writes auto, home, and life insurance for Chicago-area clients from its South Indiana Avenue office in the Bronzeville area.

Paul Cohen

Cohen Insurance Agency (Paul Cohen Insurance)

220 W Campus Dr Ste 100, Arlington Heights, IL 60004

Paul Cohen runs Cohen Insurance Agency from Arlington Heights, roughly 24 miles northwest of the Loop, serving Chicago-area clients with auto, home, and life insurance. Cohen's own site states the agency is proudly working with the LGBTQ community, with dedicated content addressing the distinct financial challenges facing LGBTQ individuals and families — from adding a partner to a life insurance policy to planning for a shared future. The agency is listed in the GaySurance.com directory for the Chicago/Illinois region. Cohen has no stated ownership tie to the LGBTQ+ community; the practice is built around marketing to and serving it.

Brian ThompsonJD

Brian Thompson Financial LLC

Brian Thompson, JD, CFP®, is founder of Brian Thompson Financial, a fee-only financial and business planning practice serving Chicago and clients nationwide. On his own site, Thompson writes that he specializes in comprehensive financial and business planning for LGBTQ+ entrepreneurs who run mission-driven businesses, adding, "As your financial and business advisor, I'm also your ally." He is listed with the LGBT Chamber of Commerce of Illinois. Insurance — specifically life insurance — is one of several services Thompson offers alongside broader financial planning and tax advisory work; he is not a dedicated insurance agency.

Michael Plageman

Plageman Agency Inc - American Family Insurance

3257 N Sheffield Ave Suite 101, Chicago, IL 60657

Michael Plageman runs the Plageman Agency, an American Family Insurance agency located at Century Mall in Chicago's Lakeview neighborhood, near Diversey and Clark. The agency writes auto, home, and life insurance for Chicago-area clients and is a member of the LGBT Chamber of Commerce of Illinois. Plageman's own site does not include LGBTQ-specific language beyond that membership, so his inclusion here reflects chamber affiliation rather than a stated ownership or ally claim.

David Flores

Cotinuum Insurance Agency

David Flores is Founder of Cotinuum Insurance Agency, based in Vernon Hills, a north suburb of Chicago. The agency focuses on individual health coverage, including ACA marketplace and Medicare plans, alongside life insurance for clients across the Chicago metro area. Cotinuum is a listed member of the LGBT Chamber of Commerce of Illinois. The agency's own website does not include LGBTQ-specific messaging beyond that chamber affiliation, so its inclusion here reflects membership rather than any stated ownership or ally language.

Jeremiah Stevens

Daddy Bear Insurance Agency LLC

Jeremiah Stevens founded Daddy Bear Insurance Agency, a Chicago-based life and health insurance brokerage affiliated with Symmetry Financial Group. On the agency's own site, Stevens writes that he started the business after seeing how many people in "our LGBTQ+ community were struggling to find inclusive, judgment-free support" for life and health coverage, building it around "community, connection, and care" — because, in his words, when "our LGBTQ+ community thrives... we all do." Daddy Bear is a member of the LGBT Chamber of Commerce of Illinois and works with more than 80 carriers nationwide to write life insurance for individuals, chosen families, and non-traditional households, under the tagline "Protect yourself and everyone in your den."