Match Your Business to Reliable Capital
Broker-led placement connects your needs with lenders built for deals from $1 to $5 million.
Secure Funding That Aligns With Your Goals
Broker-guided placement with clear scope and financial clarity
Mccullough Insurance Group serves small and midsize businesses in Chicago and surrounding areas with commercial lending and group health insurance solutions. As a broker, we specialize in matching your funding needs—whether it's working capital, real estate financing, equipment investment, or growth capital—with lenders whose underwriting criteria fit your deal structure. Chicago employers face rising costs, competitive hiring, and evolving opportunities, and the right financial strategy starts with a partner who understands your industry and timeline.
You'll work with us to define your funding goals, timeline, and current position. We evaluate your needs and present options from lenders positioned to support deals ranging from $1 to $5 million. Each placement is guided by your business objectives, not a generic product lineup, so you can move forward with confidence and realistic expectations.
Mccullough Insurance Group builds relationships around long-term financial planning. Whether you're managing benefit costs for your team or seeking capital for the next phase of growth, we focus on outcomes that support your business over time. You'll receive straightforward guidance, and we'll stay engaged as your priorities shift.
Reach out to discuss your funding or benefit needs in Chicago and learn how broker-led placement works for your business.
Group Health Insurance
Benefit solutions designed to help you manage costs and compete in tight labor markets.
About Us
Whether you're exploring commercial lending options or evaluating small group health solutions, we're here to help.
Contact Us
Discover how independent advisory services can open doors for your business in Chicago.
Our Service Area
- Evanston IL
- Chicago, IL
- Tinley Park, IL
- Orland Park, IL
- Calumet City
- Oak Park, IL
Build Financial Strategy That Fits Your Growth
Access lending and health solutions tailored to small and midsize business realities.

Our process centers on understanding your business, clarifying your funding or benefit goals, and connecting you with the right resources. You'll have visibility into what each step involves, from initial review through lender matching and final placement. We coordinate the details so you can focus on running your company while we handle the research, documentation, and follow-through.
You can expect regular updates as your deal progresses. We outline what's needed, when it's due, and what comes next, so there's no guesswork. Every step is documented, and you'll know who's responsible for what along the way.
This approach is built around delivering results you can plan for, including:
How Placement and Planning Unfold
Lender matching based on your deal size, industry, and underwriting fit
Transparent review of funding structures, terms, and timelines before you commit
Coordination across working capital, real estate, equipment, and growth capital options
Chicago-area insight into labor market pressures and benefit cost management strategies
Contact us in Chicago to start the conversation about your
commercial lending or group health insurance needs.
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A Broker Focused on Lasting Results
Mccullough Insurance Group works with business owners across Chicago who need more than off-the-shelf solutions. We bring a relationship-driven approach to every engagement, whether you're exploring your first capital raise or refining your team's health benefits. Our familiarity with the Chicago market means we understand the pressures you're facing and the opportunities in front of you.
We're here to provide dependable guidance rooted in your financial goals and operational reality. You'll work with a broker committed to your long-term success, not just a single transaction. Our focus is on building partnerships that adapt as your business grows and your needs evolve.
Call Mccullough Insurance Group in Chicago to explore how we can support your next move with capital or benefits that fit.
Phone
Location
Matteson, IL
60443
Hours
- Mon - Fri
- -
- Sat - Sun
- Closed




