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Tax Planning

Effective tax planning is essential to maximizing your business's profitability and long-term enterprise value. Our tax practice partners with business owners, CFOs, and financial advisors to develop proactive strategies that minimize tax liability while maintaining full compliance with federal, Illinois, and Chicago tax requirements.

Overview

Tax Planning in Chicago

Tax planning for businesses operating in Illinois involves navigating a multi-layered system of federal, state, and local tax obligations that creates both significant exposure and strategic opportunity. Illinois imposes a flat corporate income tax rate in addition to the personal property replacement tax, and Chicago imposes its own suite of taxes including the Chicago Personal Property Lease Transaction Tax, the Chicago Amusement Tax (which has been applied to streaming services), and various industry-specific levies. Our tax practice works closely with business owners, executives, CFOs, and outside accounting firms to develop comprehensive tax strategies that minimize liability at every level while maintaining full compliance and audit defensibility.

From entity selection and restructuring to transaction tax planning, state and local tax (SALT) compliance, R&D tax credits, and tax controversy representation before the IRS and the Illinois Department of Revenue, we integrate tax considerations into every aspect of your business strategy. Our team monitors the constantly evolving federal and Illinois tax landscape — including the implications of recent federal tax reform, changes to Illinois income tax rates, and new Cook County and Chicago tax ordinances — to ensure our clients capture every available advantage. We take a proactive approach, identifying planning opportunities in the third and fourth quarters rather than simply reacting at year-end or during return preparation.

Our Services

What We Handle

Corporate Tax Planning & Strategy

Developing comprehensive annual and multi-year tax strategies that optimize your company's effective tax rate across federal, Illinois, and local tax obligations.

Entity Selection & Restructuring for Tax Efficiency

Analyzing and implementing entity structures — including S-Corp elections, LLC conversions, and holding company arrangements — that minimize total tax burden.

Transaction Tax Structuring

Planning the tax aspects of acquisitions, dispositions, mergers, and joint ventures including purchase price allocation, Section 338 elections, and installment sale treatment.

State & Local Tax (SALT) Compliance

Managing Illinois income tax, personal property replacement tax, sales and use tax, and Chicago-specific tax obligations including lease transaction and amusement taxes.

R&D Tax Credit Analysis

Identifying and documenting qualifying research and development activities for federal and Illinois R&D tax credits that can substantially reduce your tax liability.

Tax Controversy & Audit Representation

Representing businesses in IRS audits, Illinois Department of Revenue examinations, and Cook County tax proceedings, negotiating favorable resolutions and penalty abatements.

Business Succession & Estate Tax Planning

Structuring ownership transfers, buy-sell agreements, and succession plans to minimize estate and gift tax exposure while ensuring continuity of your business.

Our Process

Our Approach

1

Tax Position Analysis

We analyze your current entity structure, tax filings, effective tax rate, and existing planning to establish a comprehensive baseline and identify immediate opportunities.

2

Strategy Development & Modeling

We design a multi-year tax strategy with financial modeling of different scenarios, considering entity structure, income timing, deduction optimization, credit utilization, and state tax implications.

3

Implementation & Documentation

We execute the tax strategy through entity restructuring, agreement amendments, election filings, and comprehensive documentation supporting each tax position taken.

4

Ongoing Monitoring & Optimization

We monitor federal and Illinois tax law changes, review quarterly estimated tax positions, and adjust strategy as your business evolves to maintain optimal tax positioning year over year.

Free Tool

Business Valuation Estimator

Understand your company's value for tax planning purposes.

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FAQ

Frequently Asked Questions

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Schedule a free consultation with one of our experienced tax planning attorneys.