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The Highest Order We Serve, 

Helping You Create a More Predictable Path.

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Money is one of the many forms that abundance has to offer. 

Money, if managed wisely, can help us experience True Wealth.

Boutique and Independent - A Firm Founded to Represent You

Legacy Advisors is dedicated to providing comprehensive, transparent financial planning and wealth management to a select group of Self-Made Entrepreneurs and Small Business owners throughout the "South Shore" areas of Chicago, NW Indiana, and SW Michigan. As an independent, fiduciary firm, we are 100% focused on delivering what is best for you. We work directly with our clients on a consultative basis, with a specific focus on business, life, and financial transitions.


Your Goals and Needs are Unique - Your Plan Should be too

We believe the Financial Planning Process to be highly individualized. Before trying to understand your numbers, we strive to understand you. The close relationships we have with our clients serve as the foundation for all future planning, enabling us to provide tailored financial advice, customized portfolio management, and personalized services.



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Who We Are

Access A Team of Advisors

Our team of professionals is here to help walk you through the many aspects that make up financial well-being. By utilizing our entire staff for each individual client, we are able to provide rapid communication, quick access, and a more hands-on, intimate advising experience that brings clarity to your specific goals.


Collaborating with Your Other Professionals

We work on your behalf with the myriad of advisors that surround you, ranging from lawyers to accountants to insurance professionals. We speak the language that makes those relationships work well together in a coordinated fashion, allowing all of your advisors to work together to help you work towards your goals.

Chris Winkler
President & Principal

Chris Winkler is the President of Legacy Advisors. He brings more than 20 years of experience in providing proactive wealth planning and asset management counsel to the firm’s clients. Chris leads our experienced team of advisors with a wealth of knowledge related to portfolio design, risk management, estate and tax minimization strategies. Legacy Advisors currently manages investments for institutions, endowments, and private investors throughout the United States.

After attending Purdue University, Chris began his career with a national investment firm in 1996. As Senior and Executive Vice President his responsibilities included strategic account management, enterprise marketing, and advisor development. He has been a keynote speaker for numerous industry-best practice symposiums, speaking in front of as many as 15,000 attendees. Chris has also served on numerous non-profit boards throughout his career.

"Our commitment is to operate and provide a World-Class experience for both our clients and our advisors. We recognize and value the trust our clients place in us and the responsibilities that come with this. With these priorities, we work hard to be a proactive resource, providing industry leading concepts and service."

Chris enjoys maintaining an active lifestyle with his family away from the office. He & his wife, Lauren, enjoy fine dining, travel, golf and are sports fan of all things Chicago.



Brad Alvarez
Director of Operations  

I began my career in financial services over a decade ago after serving 6 years in the US Navy’s nuclear field. While in the Navy, I developed an interest for learning the rules of money and investing. Being the first major step in my working career, I knew that I wanted to start the good habit of putting money away systematically early in my working life. What started as just an interest very quickly turned into a passion, and as I continued learning more, I realized this was the career route I wanted to take when I was finished with my service time. During my last year of service, I was able to gain valuable financial counseling experience when selected to become certified as a Command Financial Specialist for the submarine USS Michigan.

Upon leaving the military in 2005, I joined a national investment firm, where I had roles in branch development, compliance, product training, and rep development. In 2009, I was recruited by Legacy Advisors. As Director of Operations, my role includes support to many areas of the firm, including portfolio design and research, account servicing, and branch compliance.

Although I completely understand that money and investing can bring with it emotional challenges to many people, I take great pride in our duty to operate with a scientific priority to portfolio design, holding a high regard for research, process, and time-tested data. At Legacy, we know that clients benefit most when we combine this research and experience to solve their investment needs. This is what keeps me passionate about the work that we do.

My wife Kristina and I love of the many beaches, trails, and natural environments of the Indiana Dunes area on Lake Michigan, which is why we planted our flag in Miller Beach, IN.  We share a dune-top home with our many rescued four-legged children.

I hold General Securities Representative (Series 7) and Uniform Combined State Law (Series 66) registrations, and also maintain a state Life, Accident, & Health Insurance license.


Serving greater Chicago, Northwest Indiana, and southwest michigan

Our goal is to make the process of dealing with your finances as stress-free as possible, and one way we do this is by meeting with you in whatever manner is most convenient and comfortable to you.

We are located in Northwest Indiana, however we are happy to work with clients in person, virtually via the internet, or over the phone—typically it's a combination of methods to make things easy on everyone involved.

We work with clients throughout Chicago, NW Indiana, and SW Michigan:

Valparaiso, Chesterton, Crown Point, Portage, Porter, Michigan City, New Buffalo, Dyer, St. John, Munster, Ogden Dunes, Miller Beach, Beverly Shores, New Buffalo, St. Joseph, La Porte

 For over two decades, Loring Ward has provided portfolio management and back-office services to some of America’s most knowledgeable and successful independent financial advisors and their clients. These services include client reporting, portfolio management, operational processing, securities trading, and educational and training support.

Loring Ward’s support services allow advisors to spend more time working with clients and less time dealing with the day-to-day management of operational details Legacy Advisors receives a high level of service from Loring Ward including a dedicated administrative team assigned to servicing the needs of our firm and our clients. Loring Ward is headquartered in San Jose, California.

Our clients benefit from this partnership with Loring Ward through increased research from their investment committee which includes Nobel Prize Laureate, Harry Markowitz, and nationally recognized behavioral finance expert, Meir Statman


Dimensional Fund Advisors (DFA) is a leader in developing asset class portfolios for institutional investors and independent investment advisors. Dimensional Fund Advisors’ investments are designed to meet the needs of professional investors, and the firm’s resources are devoted to improving these strategies wherever possible.

Investments are not available directly to individuals but are limited to clients of a select group of financial advisory firms. Our relationship with Dimensional Fund Advisors is based on shared views about how capital markets work and how best to provide clients with a successful investment experience.

DFA’s investment strategies are supported by extensive historical research, which documents a reward for taking risk. Since the firm was founded in 1981, DFA has continued to work with some of the world’s leading financial economists to develop and enhance its strategies.



National Financial - Fidelity

National Financial is a pioneering firm with a long history of working with independent financial advisors. They are one of the largest providers of dedicated custodial services to the independent investment advisor community.

As a Fidelity Investments company, National Financial put the strength, resources, and experience of one of the world's largest providers of financial services to work for you.

  • The largest brokerage platform in the industry with $5.1 trillion in assets under administration
  • Investments in technology to offer the scale and scope that helps firms drive efficient results and manage costs.
  • Financial strength with net capital of $2.7 B, exceeding requirements by $2.2 billion.


Envestnet is a leading provider of integrated portfolio, practice management, and reporting solutions to independent financial advisors and institutions. Our open architecture platform encompasses a broad range of institutional research, investment products, and advisory resources. As of October 1, 2014, the firm has grown to serve more than $683B in total platform assets and nearly 2.8 million investor accounts.


 With more than 2,000 independent advisors, Securities America is one of the nation’s largest independent broker/dealers providing our firm with critical compliance and regulatory support.

Based in Omaha, Nebraska, and founded in 1984, Securities America prides itself on providing exceptional service, focusing on doing business in a friendly, efficient and effective way.



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Who We Serve

Helping You Navigate the Complexities of Life's Transitions

Most people only build a highly organized financial plan when there’s a life event that triggers them into action. For example:

  • a business owner(s) selling or divesting interests in their company
  • a physician selling their private practice to a hospital
  • a career professional planning for retirement and looking to combine company benefits with individual savings

For many, this can feel like an overwhelmingly difficult and stressful process to engage in. At Legacy Advisors, we make this process easier for you. Through devoted services and highly trained, experienced advisors, we strive to provide you with: 

A Stress-Free Financial Overview Process

Helpful Insight

Unique, Integrated Plans to Meet Your Needs

Our goal is to work with you to develop a conflict-free model that reduces your involvement, takes the emotion out of investment decision-making, and guides you to pursue decisions that better help you work towards your goals and needs.

Clarity and Transparency

Our management fee is a percentage of your assets under our management. It is not dependent on particular products or investments and is adjusted based on portfolio size and complexity.  We feel this is the most appropriate structure as it keeps our objectives in line with your objectives as a client -- our compensation rises only if the value of your account rises.  Our goal is to have clients "for life," which is only possible if we are constantly focused on doing right by you.



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What We Do

Financial Planning & Asset Management  - The Core of Wealth Management

Wealth management is a process built around financial planning and asset management. At Legacy Advisors, we view these two approaches as inseparable components of a successful financial life.  

Disciplined in Our Approach

After many years working with clients, we understand that over your lifetime there will be economic, political, and market events that create significant emotional hurdles, oftentimes leaving you wanting to make a quick decision regarding your finances. We keep you focused on your long-term goals and ensure you don't get in your own way.

We believe the true value of a financial advisor manifests itself as being a behavioral investment counselor. We help to bridge the behavior gap- the difference between returns of an investment vs. the returns of the average investor. 

The bottom line?  We keep you accountable to your future self, making sure you stay focused on what's truly important.

Investing Starts With a Plan

Whether looking to plan for retirement, saving for your child’s college education, or managing wealth, at Legacy Advisors we work directly with you to meet your needs and come up with a tailored financial solution that best addresses your goals. 

A Goal-Based Approach

Financial wellness is all about balance. You have dreams and goals for your life, but you also have the day-to-day minutiae of your life to attend to. That's where we come in - we are your trusted advisor, providing you with the guidance you need so you can have confidence in knowing you’re on track.

Our Investment Philosophy

At Legacy Advisors, our Investment Philosophy is based on almost nine decades of data, analysis and research, insights from behavioral finance, and close relationships with leading academics. Investing makes it possible for many of us to pursue important lifetime goals. A better wealth experience requires a consistent investment approach based on financial science and grounded in real- world results. 

"Evidence Based" Investing Supported by Academic Research

Because you cannot control the market, you should make sure you have a long term plan in place with the goal of capturing market returns while pursuing your deeply held goals. Accordingly, our long-term investment strategies are well diversified, low cost, tax efficient, and strategically rebalanced so as to best reflect your risks, goals, experience, and time horizon.  We call this approach Asset Class Investing.

Asset Class Investing

How Asset Class Investing can work for you and your family:

1. It focuses your investment portfolio on meeting your life goals.

  • It is an approach designed to help you manage towards your most important goals rather than to short-term market trends.

2. It is based on science and academic research.

  • It combines the latest discoveries in economics and investing with close to 90 years of market data and insights as well as in-depth studies of investor psychology and behavior.

3. It is a disciplined and structured approach.

  • It helps protect against the common behavioral mistakes that can compromise your long-term financial goals.


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Legacy Advisors


160 Rail Rd, Suite 4
Chesterton, IN 46304





We can work both virtually, or in person.  Centrally located for your convenience less than an hour drive from Chicago, St. Joseph, MI, or South Bend, IN. 

Located just 5 mins south of I-94

Take exit 26A onto IN-49 S toward Chesterton/Valparaiso
Continue on IN-49 S for 2mi to E 1100 N (intersection has stoplight)
Turn right onto E 1100 N
Turn left at the 1st cross street onto N 100 E
Turn left onto Rail Rd; Office complex will be on the left

Located just 1 mi north of Indiana Toll Road (I-80/90):

Take exit 31 for IN-49 toward Chesterton/Valparaiso.
Turn left (north) onto IN-49 N / N Calumet Ave
Turn left at the 1st cross street onto Voyage Blvd (intersection does not have a light)
Continue onto N 100 E (road will curve to the right) for about 0.5mi
Turn right onto Rail Rd; Office complex will be on the left