Business insurance Illinois & Wisconsin

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Protect Your Business, Big or Small

Local Insight, Clear Choices, and Coverage That Fits How You Operate

From Main Street shops in Rochelle and Sycamore to contractors in Rockford, food trucks in Madison, and professional offices across Chicagoland, Maple Leaf Insurance Agency builds business insurance Illinois and Wisconsin owners can rely on. We listen first—how you work, who you serve, where you’re exposed—and then tailor a plan that can grow with your LLC or established company.


Our Business Insurance Offerings

Core Coverages Most Companies Need


Every business is different, but many start with a practical mix of protection. We’ll explain each option in plain English and help you decide what belongs in your plan today—and what can wait until the next stage.


For small to mid-sized operations, a Business Owners Policy combines property coverage for your space and gear with general liability for customer incidents. We can add endorsements and extras as you grow.


Commercial spaces, equipment, and inventory are covered under commercial property insurance against losses like fire, theft, and certain weather events.


Your everyday liability to the public—slips, trips, and product or completed work claims—lives under general liability insurance.


If you drive for work, commercial auto insurance covers your vehicles, from sales cars and pickups to delivery vans.


Most Illinois employers and many in Wisconsin need workers’ compensation insurance to handle employee injuries on the job.


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Tailored Insurance for Your Industry

Coverage That Respects How You Actually Work

Retail shops need protection for inventory, customer foot traffic, and equipment breakdowns. Restaurants and food trucks often add business interruption and spoilage. Contractors may need inland marine for tools, installation floater coverage, and certificates of insurance on tight timelines. Professional services—consultants, tech firms, salons—look closely at E&O and data risks. Whatever you do in Illinois or Wisconsin, we’ll shape a clear, right-sized plan that isn’t bloated with extras you don’t need.

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As an independent commercial insurance agency, we shop multiple carriers—including regional programs well-suited to Midwest businesses—to balance price and protection. Expect fast help with certificates, same-day answers when you’re signing a lease or contract, and guidance to avoid gaps (like business income, hired/non-owned auto, or cyber). When claims happen—from a kitchen fire in Rockford to winter slip-and-falls near the Fox Valley—we’re here to help you navigate, not just hand you a phone number.


For certain industries and budgets, a carrier like Erie Insurance can be a great fit; we’ll compare options and explain the trade-offs so you can decide confidently.

Why Maple Leaf for Business Insurance?

Independent, Responsive, and Invested in Your Success

Get a Commercial Insurance Quote

Start With a Short Conversation

Tell us about your location, team, vehicles, and daily operations. Whether you’re a one-person LLC or managing dozens of employees across Illinois and Wisconsin, we’ll build a straightforward plan and keep it easy at renewal.