Tax planning and preparation for Illinois Small Businesses

Helpful Information

2025 Tips For Stress-Free Tax Filing
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Gather Your Documents Early

Begin by collecting all necessary records—W-2s, 1099s, investment statements, mortgage statements, and energy credits—well before tax season. Early preparation helps ensure accurate tax filing and prevents last-minute surprises in your tax return.

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Leverage Retirement Account Contributions

Contributions to Traditional IRAs, 401(k)s, and Roth IRAs can lower your taxable income and grow long-term wealth. This is one of the most effective tax planning strategies available in 2025, whether you’re an employee, freelancer, or small business owner. Chicagoland CPAs+2Chicagoland CPAs+2

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Take Advantage of Updated Tax Brackets

The IRS has adjusted 2025 tax brackets upward for inflation, which may reduce your tax liability. For instance, the top marginal rate of 37% now applies only to incomes over $751,600 for married couples and $626,350 for individuals. These bracket updates can influence your decisions on retirement withdrawals and estimated payments. The Wall Street Journal

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Maximize Federal Deductions & Credits

The One Big Beautiful Bill (OBBB) brings important benefits for 2025 tax filers, including permanent lower tax brackets, higher estate and gift tax exemptions, enhanced deductions for seniors, and bigger standard deductions. Temporary provisions—like expanded SALT deductions and deductions on tips, overtime, and car loan interest—provide additional tax-saving opportunities. The Sun+7Kiplinger+7Kiplinger+7

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Track Self-Employment and Business Expenses Carefully

Self-employed individuals should diligently log all white-collar expenses—home office, equipment, software subscriptions, professional fees—and travel or freelance costs. Many of these can be fully deducted, reducing your taxable income significantly. ICPAPorte Brown

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Update Withholdings and Plan for Quarterly Taxes

Mid-year life changes—like marriage, divorce, a pay raise, or side gig income—often warrant revisiting your tax withholdings and estimated payments. Use official IRS tools like the Withholding Estimator to minimize underpayment penalties. Kiplinger+2irs.gov+2

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Note Changes in Illinois State Tax Law

The flat Illinois income tax rate remains at 4.95% for all individual taxpayers, with no tiered rates to complicate filings. Keep this in mind as you plan for combined state and federal liabilities. blog.turbotax.intuit.com
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Don’t Ignore Free Tax Assistance Resources

If your income is limited, Chicago offers free tax prep support through programs like Ladder Up and TaxPrepChicago.org. These IRS-certified services are a valuable way to get accurate help without the expense. chicago.gov+1

Helpful Information

Summary Table: 2025 Tax Tips at a Glance

This summary table provides a quick reference to the most important 2025 tax tips, helping individuals and businesses in Chicago and across Illinois stay compliant, maximize savings, and plan ahead with confidence

Tip

What to Do

Document Organization

Collect all income, expense, and deduction records early

Retirement Contributions

Maximize IRA/401(k) contributions to lower taxable income

New Tax Brackets

Leverage inflation-adjusted thresholds to your advantage

OBBB Provisions

Tap into temporary and permanent deductions and credits

Self-Employed Deductions

Track all business-related expenses diligently

Withholding Updates

Reassess your withholdings and quarterly payments after life changes

IL Flat Tax

Account for Illinois’s flat 4.95% income tax rate

Free Assistance

Use certified programs if you qualify for free tax help