Calculate your federal, Illinois state taxes on freelance and self-employment income. Free and accurate for 2026.
If you're a freelancer, independent contractor, or self-employed professional in Chicago, Illinois, understanding your tax obligations is crucial. Unlike W-2 employees who have taxes automatically withheld, 1099 workers are responsible for calculating and paying their own taxes throughout the year.
As a Chicago freelancer, you're required to make quarterly estimated tax payments if you expect to owe $1,000 or more in taxes. The IRS due dates are:
Missing these deadlines can result in underpayment penalties. WorkMade automatically calculates and can even pay your quarterly taxes for you.
Reduce your tax bill by tracking these common business expenses:
Freelancers in Chicago pay self-employment tax (15.3%), federal income tax (10-37%), Illinois state tax (4.95%). Total effective rate is typically 25-40% depending on income and deductions.
No, Chicago does not have a local income tax. You'll only pay Illinois state tax and federal taxes.
Quarterly estimated tax payments for Chicago freelancers are due on April 15, June 15, September 15, and January 15 of the following year. These dates apply to federal taxes and most state taxes.
Chicago freelancers can deduct business expenses like home office costs, equipment, software, professional development, travel, and health insurance premiums. These deductions reduce your taxable income for federal, state taxes.
Chicago has no local income tax, which is good. You'll pay Illinois's 4.95% state tax plus federal taxes. The state tax rate is moderate.
WorkMade tracks your income, finds write-offs, calculates quarterly taxes, and files your return. No spreadsheets required.
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