About Longmeadow Insurance

At Longmeadow Insurance, we believe insurance isn’t just a transaction. It’s the foundation of your financial security. The agency was founded on a simple premise: families and business owners across Chicago deserve the same analytical rigour that large companies expect from their risk advisors.

Longmeadow is led by Tom Firestine, CPCU, RPLU, who spent two decades in the industry before founding the agency in 2025. The CPCU is the property and casualty field’s most demanding designation, and the RPLU covers professional liability specifically. He holds an MBA from the University of Chicago Booth School of Business.

That background is why we read a policy before quoting against it. Most agencies price what you already have. We look at what your dwelling limit would actually rebuild, where your liability limits sit relative to your assets, and which exclusions matter for your specific address, then take that analysis to the carriers.

We’re independent, which means we answer to you, not a corporate headquarters. We compare the market on your behalf, matching you to the right carrier and coverage for your specific life stage, so everything you’ve worked hard to build stays protected.

Rooted in the North Shore, Serving All of Chicago
Longmeadow is headquartered in Wilmette, on Chicago’s North Shore, with satellite offices throughout the city and suburbs, including Evanston, Wicker Park, Lakeview, North Center, Elmhurst, Elk Grove Village, and Antioch. Wherever you live or do business, we serve clients from an office nearby and know the neighborhood.

Deep Roots in the Community
Longmeadow Insurance isn’t just a business, it’s a neighbor. We drive the same roads, deal with the same unpredictable Midwest weather, and care about the same local schools and businesses our clients do. We live and work in these communities, and we plan to be here for the long run.