Craig Caimi is a Financial Advisor with WestPoint Financial Group, where he partners with individuals, families, and business owners to build clear, comprehensive, and lasting financial strategies. Craig believes effective planning begins with truly understanding what matters most to each client. By taking the time to listen and learn their priorities, he designs personalized roadmaps that adapt as life evolves—providing clarity today and confidence for the future.
His experience spans retirement income planning, education funding, tax-efficient strategies, wealth transfer, and risk management. Whether clients are preparing for major milestones, protecting their families, optimizing insurance solutions, or seeking purpose-driven wealth strategies, Craig delivers transparent, thoughtful guidance every step of the way.
At WestPoint Financial Group, Craig is part of a boutique planning firm committed to helping clients grow and safeguard their wealth with intention. He works closely with business owners, executives, and high-achieving professionals to provide strategic solutions across insurance, investments, non-correlated assets, and holistic financial planning. Through a collaborative approach, Craig helps clients identify challenges, prioritize goals, and gain peace of mind through smart, well-structured strategies.
Outside the office, Craig enjoys a full and active life with his wife and three children. He is engaged in his local community through the Skokie and Edgebrook Chambers of Commerce, the Chicago Corinthian Yacht Club, and through his support of neighborhood schools such as Edgebrook Elementary and Northside College Prep. In his free time, Craig can often be found sailing on Lake Michigan, reading, skiing, hiking, exploring great food, and cheering on Michigan State.
