About Mccullough Insurance Group in Chicago, IL

Independent Advisory Built for Growing Businesses in Chicago

When you're navigating commercial lending or searching for the right health solutions for your team, you deserve more than a single option from one institution. You need access to multiple lenders and carriers who understand your business and can support your goals. That's exactly what Mccullough Insurance Group delivers to business owners across Chicago and the surrounding areas.



We're an independent advisory firm focused on commercial lending and employer health solutions for growing businesses. Our foundation is built on education, transparency, and strategic deal structuring designed to improve your approval odds and long-term outcomes.


We believe in honesty, reliability, and a customer-first approach that puts your objectives at the center of every conversation.


Discover how independent advisory services can open doors for your business in Chicago.

Where Commercial Lending Meets Strategic Health Solutions

We work closely with local entrepreneurs, property owners, and employers throughout the Chicago metro area who are ready to grow but need the right financial structure or benefits strategy to make it happen. Whether you're securing capital for expansion, refinancing a commercial property, or designing small group health coverage that attracts and retains talent, we connect you with the right partners and guide you through every step.



From the energy of the Loop to the neighborhoods stretching across the North Side, South Side, and western suburbs, Chicago businesses face unique challenges and opportunities. We understand the pace, the competition, and the capital needs that come with operating in one of the nation's most dynamic metro areas.


We're proud to support business owners across Chicago, helping our community thrive through access, advocacy, and actionable guidance.


Let's talk about what your business needs to move forward.

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Our experienced team knows Chicago businesses inside and out, and we treat each client relationship as if your success were our own. We're known for a consultative, hands-on process from initial review through funding or enrollment, and we're experienced in navigating complex lending criteria, timelines, and capital needs across different business stages.

Experience That Guides You From Review to Funding

Independent access to multiple lenders and carriers, not just one institution

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Deep experience with commercial lending deal structuring and employer health plan design

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Transparent education throughout the process so you understand your options

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Close partnership with entrepreneurs and employers across the Chicago metro area

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Strategy-focused approach that aligns financing and benefits with your long-term business goals

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Whether you're exploring commercial lending options or evaluating small group health solutions, we're here to help. Connect with us today for a strategy-focused conversation about your business goals in Chicago, IL. We'll walk you through your options and help you build a plan that works.