CWI Insurance Services
The CommonWealth Initiative™ is a Chicago-based financial planning and consulting firm specializing in budgeting, money management, and financial services. Our services are confidential, forward-thinking and affordable, with the purpose to promote financial “well-being” for the “common-good”.
CWIMONEY, Financial Planning, Financial Planner, Free Consultation, Estate Planning, Estate Planner, Business Consulting, Business Consultant, CWI, CWI University, Money, Chicago Money,
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Getting started is easier than you think.


CWI Life Insurance

Life and Health Insurance

CWI is a Chicago-based independent insurance brokerage that provides access to coverages ranging from life insurance, disability income insurance, and business insurance to annuity and retirement planning. Our portfolio of insurance carriers is highly rated and provides the best coverage and protection.

Our licensed team of professional understand the importance of covering all your financial bases and appreciate the primacy of saving money. Before establishing a plan specific to their needs and goals, CWI provides clients with a complimentary and confidential financial assessment to help them know where they are financially and to map out a plan to achieve those goals! Our clients have access to top-rated insurance and financial carriers offering:

  • Life Insurance
    • Term Life
    • Whole Life
    • Final Expense (No Medical Exam Required)
  • Health Insurance
  • Disability Income Insurance
  • Long-Term Care Coverage
  • Group Employee Benefits
  • Retirement Planning
  • Medicare Supplements

Our Commitment

At CWI, we take pride in providing a more straightforward, educational, and client-centered approach to insurance services. We offer competitive rates and provide access to educational resources, especially for seniors and those living with more common chronic conditions.

Our Mission

To change lives financially, protecting one person, one family, and one business at a time.

To speak with a CWI financial professional and begin to discover solutions to protect what is most important to you, contact us at 312-574-0866, or schedule your discovery call online!

Business Insurance

At CWI, we provide comprehensive, tailored business insurance solutions to help protect your income, employees, business, and reputation. No matter the type of business or industry, whether virtual or brick-and-mortar, one employee or thousands, business insurance is critical for your protection. CWI enables you to continue focusing on what is most important, your business’s success. Our clients have access to top-rated insurance and financial carriers offering the following business coverages:

  • General Liability
  • Professional Liability
  • Errors & Ommissions
  • Key Person


Speak with a CWI financial professional today and begin to discover solutions to protect what is most important to you.



Are you looking for a reliable retirement income that will last your entire life? When it comes to your income in retirement, slow and steady wins the financial race. Consider adding a fixed annuity to your retirement income strategy where you can protect your savings and enjoy a predictable source of income for life. Certain annuities can help protect your retirement from market volatility, inflation, and outliving your money.


Our clients have access to top-rated insurance and financial carriers offering the following types of annuity products:

  • Fixed Annuities
  • Fixed Indexed Annuities


Speak with a CWI financial professional to discuss your financial goals today.

FAQ’s (Frequently Asked Questions)


Starting coverage is easy. Complete the online quote form, and one of our licensed CWI Financial professionals will contact you to discuss coverage options and pricing.


We conduct a CWI Financial Assessment that includes understanding your current & future financial goals, debt obligations, and family members you want to cover to determine adequate coverage amounts and financial options.


Once your CWI Application is submitted, we’ll process the information to provide you with a quick (sometimes instant) decision on coverage eligibility and your rate. If approved, you can activate your coverage immediately.


Quite simply, at CWI, we’re your advocate! An insurance broker partners with several insurance carriers to find the best deal on insurance coverage that’s right for you. We conduct financial assessments and make impartial recommendations that serve your interests – not the interests of the insurance companies. Furthermore, since we have relationships with several insurance carriers, we can provide competitive rates and, sometimes, add several discounts.


Term life insurance

Term life insurance, as its name implies, is “temporary” insurance that is the most affordable coverage for a specific term or period. You’ll receive a guaranteed death benefit amount for the term you choose, such as a 5, 10, 15, or 20-year term, and your premium payments are guaranteed to remain the same for the term. After the term ends, coverage terminates.


Whole life insurance

Whole life insurance, also known as permanent insurance, offers a death benefit and cash value. The cash value is a separate savings component that you may be able to access while you’re still alive through loans. Permanent life insurance lasts from when you buy a policy to when you pass away if the required premiums are paid.


You can fund your annuity in several ways, including with a rollover from your existing IRA or 401(k). With some annuities, you can also add money over time. There are options for you to choose how your money is invested. Some annuities invest in the market, while others offer a fixed rate or an interest rate linked to the performance of a market index. Benefit options can address how and when you take income, whether your spouse or loved ones are covered, how much income you get, and what it costs.

Getting started is easier than you think.


Insurance Services Legal Disclaimer

CWI Financial Services provides insurance services, also referred to as “CWI Financial,” Illinois Insurance Broker License No: 3002056315.  CWI Financial Services is a CommonWealth Initiative affiliate company and a wholly-owned subsidiary of The Johnson Group, LLC.  CWI Financial is authorized to conduct life insurance business in Illinois, Ohio, and Georgia and may be licensed in other states.  CWI Financial Services does not conduct life insurance business in states they are not licensed.  CWI Financial has an affiliate team of licensed property and casualty insurance professionals in 50 states.


This website is not an offer for selling insurance or securities products in unauthorized states or countries.  Website content is for overview and informational purposes only and is not intended and should not be relied upon as individualized tax, legal, fiduciary, or investment advice.  CWI Financial Services nor their representatives provide tax or legal advice.  Please consult a qualified attorney or tax advisor to answer specific questions before making any decisions.


Guarantees are subject to the claims-paying ability of the issuing insurance company.  CWI Financial Services is not affiliated with or endorsed by the Social Security Administration, the Centers for Medicare & Medicaid Services, or any other governmental agency.

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