At Longmeadow Insurance, we believe insurance isn’t just a transaction. It’s the foundation of your financial security. After two decades in the industry Tom Firestine launched the agency in 2025 with a simple premise: families and business owners across Chicago deserve the same level of sophisticated risk management usually reserved for Fortune 500 companies.

Our team brings decades of combined experience in commercial and personal insurance to every policy we write, and we put that experience to work finding coverage built around how you actually live, not a generic one-size-fits-all policy.

We’re independent, which means we answer to you, not a corporate headquarters. We curate 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, there’s a Longmeadow team nearby who knows 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. Our team stays active in the community, from local committees to regional business organizations, because we’re invested in the long-term vitality of the places we serve.