High-Net-Worth Individual Tax Preparation, Bookkeeping & Accounting Services in Chicago
Strategic tax planning and financial clarity for high-income individuals and families. We bring investments, business income and Illinois rules into one plan, so the return reflects decisions made during the year, not just what happened.
Where high earners tend to overpay
- The 3.8% net investment income tax nobody planned for
- A SALT deduction that shrinks above $505,000 of income
- Capital gains realized in the wrong year
- Estimated payments below the 110% safe harbor
- Illinois estate tax, which starts at $4 million
- Illinois retirement income exemptions left out of the plan
Certified on the platforms our clients use
When your finances outgrow a standard tax return
High-net-worth individuals rarely have a single W-2. Income arrives from salary and bonuses, brokerage accounts, rental property, K-1s from partnerships and S corporations, and sometimes equity compensation. Each is taxed differently, reported on a different form and affected by different thresholds. Without someone looking at the whole picture, the result is usually a correct return that still costs more than it should.
Heard & Associates LLC provides tax preparation, bookkeeping and accounting services for high-income individuals and families in Chicago. We keep your financial records organized throughout the year, model the tax effect of decisions before you make them and prepare federal and Illinois returns that tie to your statements.
Our approach focuses on clarity, compliance and long-term strategy, and we coordinate with your financial advisor and estate attorney so planning across your team points in the same direction.
Tax and accounting services for high-net-worth individuals
One firm handling the return, the planning and the records behind them, so nothing falls between advisors.
Complex Individual Returns
Form 1040 with every schedule it needs: K-1s from partnerships and S corps, brokerage 1099s, rental income, equity compensation and foreign accounts, all tied to your statements.
Individual tax preparation →Tax Projections and Planning
A mid-year and year-end projection of what you will owe, so bonuses, sales, gifts and retirement moves are timed before December 31, not discovered in April.
Tax advisory →Investment and Capital Gains Reporting
Cost basis tracked across accounts, gains and losses paired deliberately, wash sales caught and the net investment income tax calculated correctly on Form 8960.
Investment income returns →Business Owner Coordination
Your S corporation or partnership return and your personal return prepared together, with reasonable salary, distributions and the Illinois pass-through entity tax election reviewed every year.
S corp tax preparation →Personal Bookkeeping
Multiple accounts, properties and income streams organized in one place, so you see the full picture each month and tax time starts from clean records.
Bookkeeping services →Trust, Estate and Gift Filings
Form 709 gift returns, Form 1041 trust returns and Illinois estate tax filings, coordinated with your estate attorney.
Trust and estate tax →The numbers that matter at higher incomes
Above certain income levels, extra taxes and phase-outs start to apply. The 3.8% net investment income tax reaches dividends, interest, capital gains and passive rental income once modified adjusted gross income passes $200,000 for single filers or $250,000 for married couples. Those thresholds are not indexed for inflation, so more households cross them every year.
The state and local tax deduction is now capped at $40,400 for 2026, but the cap shrinks for incomes above $505,000 and falls back to $10,000 once income passes $606,000. Estimated taxes are another trap: when adjusted gross income is over $150,000, the safe harbor requires paying 110% of last year’s tax, not 100%, to avoid an underpayment penalty.
Illinois tax planning for high-net-worth households
Illinois looks simple because of the flat rate, but several state rules change how a high-income household should plan:
- A flat 4.95% income tax, including on capital gains, with no city income tax in Chicago
- Most retirement income, including IRA and 401(k) withdrawals, pensions and Social Security, is not taxed by Illinois
- The pass-through entity tax election can move state tax to the business level and around the federal SALT cap
- Illinois estate tax applies to estates over $4 million, with rates reaching 16%
- The Illinois exemption is not indexed for inflation and cannot be transferred between spouses
The Illinois estate tax trap
The federal estate tax exemption is $15 million per person in 2026. Illinois starts taxing estates at $4 million, a figure unchanged since 2013. A home, a retirement account and life insurance can cross that line for many Chicago families who would never think of themselves as wealthy enough to owe estate tax.
Because Illinois does not let a surviving spouse use the first spouse’s unused exemption, married couples often need planning, such as a credit shelter trust, to avoid losing one exemption entirely. We model the exposure and coordinate with your estate attorney, who drafts the documents.
Trust and estate tax services →How we reduce taxes for high-income clients
None of these are exotic. They simply require someone to look at the whole year before it ends.
Capital gains timing
Charitable giving
Retirement and Roth planning
Business income
Gifting to family
How we work with high-net-worth clients
Private consultation
We review your last two returns, your accounts and what is changing this year.
Organize the picture
Accounts, properties, entities and basis records gathered into one organized view.
Project and plan
A mid-year and a year-end projection with specific actions and deadlines.
File and coordinate
Federal and Illinois returns prepared from clean records, with your advisors kept in the loop.
Rated 5.0 by 100+ clients on Google
Clients describe a team that is responsive, thorough and discreet, and that explains the numbers clearly before anything is filed.
High-net-worth tax questions
Every situation is different. If your question is not here, ask us during a private consultation.
Book a consultation →What does a tax accountant for high-net-worth individuals do differently?
Beyond preparing the return, the work is about mapping every income source, tracking cost basis across accounts, timing gains and losses, projecting the year before it ends and coordinating federal and Illinois rules. The goal is a return that reflects decisions made on purpose, with records that hold up if the IRS asks.
What is the net investment income tax?
A 3.8% tax on dividends, interest, capital gains, passive rental income and similar income once modified adjusted gross income exceeds $200,000 for single filers or $250,000 for married couples filing jointly. It is reported on Form 8960. The thresholds are not adjusted for inflation.
Does Illinois tax capital gains and retirement income?
Illinois taxes capital gains as ordinary income at the flat 4.95% rate. Most retirement income, including IRA and 401(k) distributions, pensions and Social Security, is excluded from Illinois income tax when it is already included in federal income.
How does the Illinois estate tax work?
Illinois taxes estates valued over $4 million, with rates reaching 16%, even though the federal exemption is $15 million per person in 2026. The Illinois exemption is not portable between spouses, so married couples often use trust planning to preserve both exemptions. We model the exposure and work alongside your estate attorney.
How much should I pay in estimated taxes?
To avoid an underpayment penalty, you generally need to pay at least 90% of this year’s tax or 100% of last year’s tax through withholding and estimates. If last year’s adjusted gross income was over $150,000, the prior-year safe harbor rises to 110%. We calculate the payments and adjust them as the year changes.
What is the Illinois pass-through entity tax election?
Owners of Illinois partnerships and S corporations can elect to have the business pay Illinois income tax at the entity level. The tax becomes a business deduction, which can work around the federal SALT cap. Whether it saves money depends on your income and deductions, so we test it each year before electing.
Can you work with my financial advisor and estate attorney?
Yes. With your permission we share projections and documents with your advisor and attorney so investment, estate and tax decisions are made together. We stay in our lane: tax and accounting, not investment advice or legal drafting.
Is my information kept confidential?
Yes. Documents are exchanged through a secure portal, access is limited to the people working on your file, and meetings can be held privately at our Hyde Park or Olympia Fields office or by video.
Plan the year before it ends
Book a private consultation. Bring your last two returns and we will show you where planning could change the result this year.