About Us
Where Protection Meets Personal Care
Serving Illinois and Wisconsin with coverage you can count on and a team you can trust.
We’re Casey and Şeyda Calderwood, and together we’ve built a family-run agency dedicated to protecting what matters most to you. At Calderwood Insurance Agency, we’ve earned the trust of families and businesses across Illinois and Wisconsin by delivering coverage that combines protection, value, and personal care. We take the time to understand what matters most to you and design solutions that fit your life and budget—whether it’s auto, home, life, or business insurance. With us, insurance isn’t just a policy—it’s peace of mind. Start today with a FREE, no-obligation quote and discover the difference of having a team who truly puts you first.
Casey Calderwood
Founder
Casey is the operational backbone of Calderwood Agency, overseeing day-to-day management with a sharp focus on client satisfaction. As Policy Strategy Advisor, he helps clients align their coverage with long-term goals, ensuring protection and peace of mind that goes beyond the basics. With extensive experience in financial services and customer care, Casey ensures every client receives timely, attentive, and results-driven support. Known for his approachable style and problem-solving expertise, he guides families and businesses through the complexities of insurance, making sure they feel secure and informed every step of the way.
Seyda Calderwood
Founder
With over five years of experience in the insurance industry and more than two decades in financial services, Şeyda brings both expertise and a personal touch to every client relationship. As the visionary behind Calderwood Agency, she is dedicated to delivering tailored protection with integrity and care. Beyond the agency, she is an active community leader, serving as President-Elect of the Rotary Club of Chicago (2026–27), Rotary One Foundation Trustee, and Board Director.