Top 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.
If you're approaching Medicare eligibility, you need an advisor who understands the timing and options for enrollment to avoid costly penalties. A common mistake is missing enrollment windows or choosing plans that don't fit your health needs and budget.
- Enrollment timing expertise. Confirm how they guide you through initial and special enrollment periods to prevent coverage gaps.
- Plan comparison skills. Ask how they evaluate Medicare Advantage, Part D, and supplemental plans based on your prescriptions and preferred providers.
- Property tax impact. Since Illinois has no tax on retirement income but high property taxes, check how they factor this into your overall retirement budget.
- Coordination with other benefits. Medicare often interacts with employer or VA benefits; ensure they consider these in your planning.
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 and general retirement strategies, offering expertise in Social Security optimization and tax planning, which is crucial for managing Illinois' high property taxes. Operating independently with a flat-fee structure, he provides personalized portfolio management and consulting services, supported by six years of experience and a Series 65 designation, distinguishing him from advisors with different fee models or less tax-focused backgrounds.
Experience: 7 years
Avg account: $1,945,307
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Christine G
Series 66
Northbrook, IL
Merrill
Christine Gregory specializes in Medicare planning and general retirement strategies, making her well-suited to help Chicago-area clients navigate enrollment timing and plan comparisons. As a Merrill advisor with 10 years of experience, she serves mid-career professionals and HENRY clients, offering a 1.10% AUM fee for managed strategies and emphasizing transparent, personalized wealth planning.
Experience: 10 years
Avg account: $860,085
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Ara B
Series 65
Chicago, IL
Bayworth Capital
Ara Bayindiryan specializes in Medicare planning and retirement income strategy, offering expertise in enrollment timing and plan comparisons crucial for Medicare eligibility in Chicago. His firm, Bayworth Capital, manages $62.7 million in assets and provides flat-fee financial planning, appealing to clients seeking independent advice with a negotiable fee structure and tailored portfolio management.
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 and independent advisory services from Itasca, IL, near Chicago. With 13 years of experience and a background at major firms, she provides long-term, diversified portfolio management and integrates tax and accounting services, distinguishing her from advisors focused solely on Medicare enrollment timing or plan comparisons.
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 and retirement income strategy, making her well-equipped to guide clients through enrollment timing and plan comparisons in the Chicago area. Her firm, Parkview Asset Management, manages $160 million with a fiduciary, long-term approach using diversified low-cost funds, and she offers flat-fee and hourly financial planning services tailored for high-net-worth clients.
Experience: 7 years
Avg account: $1,184,776
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