Flat-fee, medicare planning financial advisors in Chicago, IL
The right financial advisor for you depends on how you weigh location, expertise, experience, the clients they typically serve, and how they work with you.
You need a Medicare planning advisor if you're approaching Medicare eligibility and want to avoid costly coverage gaps or penalties. A common mistake is underestimating how different Medicare parts and supplemental plans interact, leading to unexpected expenses.
- Coverage coordination. Confirm how they help you align Medicare Parts A, B, C, and D with your health needs and budget.
- Enrollment timing. Ask how they guide you on when to sign up to prevent late enrollment penalties.
- Supplemental plan insight. Look for advisors who explain Medigap options clearly and how they complement original Medicare.
- Flat-fee clarity. These advisors charge a set fee, so you know costs upfront without surprises tied to your plan choices.
Here are top matches to get you started. Review each profile to compare experience, credentials, and approach.
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Nicholas M
Series 65
Chicago, IL
Hemsley Advisors, Ltd.
Nicholas Martin specializes in Medicare planning with a flat-fee structure, making him suitable for clients in Chicago seeking clear cost expectations. His firm, Hemsley Advisors, Ltd., offers individualized investment policies and a buy-and-hold strategy, serving individuals and organizations, which differentiates him by combining Medicare expertise with comprehensive portfolio management and tax services.
Experience: 7 years
Avg account: $1,945,307
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Darryl F
Series 66
Naperville, IL
Oakwood Wealth Advisors Ltd.
Darryl Franklin specializes in Medicare planning and Social Security optimization, offering flat-fee financial planning with fixed fees up to $42,000 annually, which suits clients seeking clear cost structures. Based in nearby Naperville, IL, he brings 17 years of experience and combines active and passive investment management, serving a diverse client base including high-net-worth individuals and trusts, differentiating him from advisors focused solely on Medicare.
Experience: 17 years
Avg account: $590,196
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Ara B
Series 65
Chicago, IL
Bayworth Capital
Ara Bayindiryan specializes in Medicare planning with nine years of experience and offers flat-fee financial planning services in Chicago, helping clients navigate Medicare Parts and supplemental plans. His firm, Bayworth Capital, manages $62.7 million in assets and provides tailored portfolios with ongoing monitoring, distinguishing him through a combination of flat-fee clarity, independent advice, and a broad investment approach.
Experience: 10 years
Avg account: $459,557
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Colleen N
Series 66, Series 63
Itasca, IL
Pendulum Wealth Partners
Colleen Nesslar specializes in Medicare planning and retirement income strategy, offering flat-fee financial planning services that provide clear cost expectations. Based in Itasca, IL, she brings 13 years of experience and works with Pendulum Wealth Partners, a firm managing $254 million with a long-term, diversified investment approach and integrated tax and accounting services, distinguishing her from other advisors in Chicago.
Experience: 13 years
Avg account: $1,043,677
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Bobbie H
Series 66
Oakbrook Terrace, IL
Parkview Asset Management, Inc.
Bobbie Helman specializes in Medicare planning with a flat-fee structure, making her well-suited for clients in Chicago seeking clear cost expectations. With seven years of experience and a Series 66 designation, she works at Parkview Asset Management, a small firm managing $160 million with a fiduciary-oriented, long-term investment approach using diversified portfolios.
Experience: 7 years
Avg account: $1,184,776
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