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Your Trusted Financial Partner in Grant Park, IL
Chesterfield Investment Services has provided trusted financial guidance for over 30 years. Our founder Robert Chesterfield combines deep industry expertise with a personalized approach to help individuals, families, and businesses navigate complex financial decisions. Specializing in insurance, investment strategies, retirement planning, and business continuity solutions, we serve clients nationwide while maintaining strong roots in Illinois. Our FINRA-registered professionals deliver tailored advice grounded in decades of market experience and a commitment to client welfare.

With affiliations including FINRA, SIPC, and MSRB, we maintain rigorous professional standards while offering comprehensive services spanning estate planning, corporate insurance, and educational IRAs. Our track record of helping clients achieve financial security reflects our dedication to both technical excellence and compassionate service.
Services
Insurance Planning Investment Management Retirement Strategies Business Continuity Estate Planning
Highlights and features
  • We offer 30+ years of experience in financial planning and investment management
  • Our personalized approach combines technical expertise with individualized attention
  • We provide comprehensive services covering insurance, retirement, and business planning
  • Our advisors maintain FINRA accreditation and industry-leading standards
  • We serve clients nationwide while maintaining local community connections
Associations and certifications
  • FINRA
  • SIPC
  • MSRB
What people say
Retirement free of financial worries Responsible, conscientious, knowledgeable person 30 years of reliable service Personalized approach to planning Expertise in financial matters
Services
Insurance Planning
We provide comprehensive insurance solutions tailored to individual and business needs. Our services cover life, disability, long-term care, and corporate insurance products. With expertise in estate planning and risk assessment, we help clients protect their assets and ensure financial security for their loved ones through customized insurance strategies.
Investment Management
Our investment advisory services include portfolio management for diverse financial instruments. We offer guidance on stocks, bonds, ETFs, and mutual funds tailored to clients' risk tolerance and financial goals. With 30+ years of market experience, we develop personalized investment strategies that adapt to changing economic conditions while maintaining focus on long-term growth objectives.
Retirement Strategies
We specialize in creating customized retirement plans including 401(k)s, IRAs, and pension solutions. Our approach considers tax implications, income needs, and life expectancy to ensure financial security in retirement. We help clients navigate qualified plans, deferred compensation arrangements, and college savings options like 529 plans to achieve their post-career objectives.
Business Continuity
Our business planning services address succession, risk management, and executive compensation needs. We help business owners develop continuity strategies, implement key person insurance, and structure ownership transitions. With expertise in corporate insurance and liability protection, we ensure businesses maintain stability through leadership changes and market fluctuations while preserving family legacies.
Estate Planning
We provide comprehensive estate planning services that coordinate with insurance and investment strategies. Our approach includes creating legacy plans, establishing trusts, and implementing tax-efficient wealth transfer methods. We work with clients to ensure their assets are distributed according to their wishes while minimizing estate taxes and legal complexities for future generations.
People
Robert Chesterfield
Financial Advisor
Robert Chesterfield has provided financial guidance for over 30 years, serving clients nationwide from his Illinois base. A FINRA-registered representative, he specializes in insurance, investment strategies, and retirement planning while maintaining affiliations with major industry organizations.
Questions
What financial services do you offer?
We provide comprehensive services including investment management, insurance planning, retirement strategies, business continuity solutions, and estate planning tailored to individual and business needs.
How can you help with retirement planning?
We create customized retirement plans using 401(k)s, IRAs, and pension solutions while considering tax implications and income needs to ensure financial security during retirement years.
Are you licensed to work nationwide?
Yes, we serve clients across the United States with licenses in California, Florida, Illinois, Iowa, and Oklahoma, while maintaining FINRA and SIPC registrations.
What makes your approach different?
Our 30+ years of experience combine with personalized service and comprehensive solutions that address both immediate needs and long-term financial goals through coordinated planning strategies.
How do you handle business succession planning?
We develop business continuity strategies including key person insurance, ownership transition plans, and executive compensation arrangements to ensure smooth leadership transitions and company stability.
What credentials do your advisors hold?
Our advisors maintain FINRA registration and industry affiliations including SIPC and MSRB, demonstrating commitment to professional standards and ongoing education in financial services.