Tax Calendar & Deadlines | Chicago Tax Strategies

Chicago Tax Calendar & Deadlines

Never miss an important tax deadline with our comprehensive calendar customized for Chicago businesses and individuals.

Stay Ahead of Tax Deadlines in Chicago

Managing tax deadlines is crucial for Chicago businesses and individuals. Missing important filing dates can result in penalties, interest, and unnecessary stress. Our comprehensive tax calendar includes all federal, Illinois state, Cook County, and Chicago-specific tax deadlines to help you stay organized and compliant throughout the year.

For Chicago taxpayers, it’s especially important to track multiple tax obligations at different governmental levels. From federal income tax deadlines to Chicago business license renewals, our calendar provides a single source for all your important tax dates.

⚠️
Important Notice for Chicago Taxpayers: Due to recent changes in Illinois state filing requirements, several deadlines have been adjusted for the current tax year. Our calendar reflects these updates.

2025 Tax Calendar for Chicago Taxpayers

January 2025
  • January 15 Federal & IL
    4th quarter estimated tax payments due for individuals and businesses
  • January 15 Chicago
    Chicago Restaurant Tax due for December 2024
  • January 20 Federal
    Monthly payroll tax deposits due for December 2024
  • January 31 Federal
    Form W-2 and 1099-NEC filing deadline
  • January 31 IL & Federal
    Quarterly federal and Illinois withholding returns due
  • January 31 Chicago
    Annual Chicago Amusement Tax Return due for qualifying businesses
February 2025
  • February 15 Chicago
    Chicago Restaurant Tax due for January 2025
  • February 20 Federal
    Monthly payroll tax deposits due for January 2025
  • February 28 Federal
    Paper filing deadline for Forms 1099 and 1096
  • February 28 Cook County
    First installment of Cook County property taxes due
  • Varies Chicago
    Chicago business license renewals (based on issue date)
March 2025
  • March 15 Federal & IL
    S-Corporation and Partnership tax returns due (Forms 1120-S and 1065)
  • March 15 Chicago
    Chicago Restaurant Tax due for February 2025
  • March 20 Federal
    Monthly payroll tax deposits due for February 2025
  • March 31 Federal
    Electronic filing deadline for Forms 1099 and 1096
  • March 31 IL
    Annual Economic Interest Statements due for certain Illinois public officials
April 2025
  • April 15 Federal & IL
    Individual and C-Corporation tax returns due
  • April 15 Federal & IL
    1st quarter estimated tax payments due for individuals and businesses
  • April 15 Federal
    Last day to contribute to IRAs and HSAs for 2024 tax year
  • April 15 Chicago
    Chicago Restaurant Tax due for March 2025
  • April 20 Federal
    Monthly payroll tax deposits due for March 2025
  • April 30 IL & Federal
    Quarterly federal and Illinois withholding returns due
May 2025
  • May 15 Federal & IL
    Form 990 due for tax-exempt organizations
  • May 15 Chicago
    Chicago Restaurant Tax due for April 2025
  • May 20 Federal
    Monthly payroll tax deposits due for April 2025
  • Varies IL
    Illinois Annual Report filing deadline (based on organization date)
June 2025
  • June 15 Federal & IL
    2nd quarter estimated tax payments due for individuals and businesses
  • June 15 Chicago
    Chicago Restaurant Tax due for May 2025
  • June 20 Federal
    Monthly payroll tax deposits due for May 2025
  • June 30 Federal
    Foreign Bank Account Report (FBAR) filing deadline
  • June 30 IL & Federal
    Quarterly federal and Illinois withholding returns due
July 2025
  • July 15 Chicago
    Chicago Restaurant Tax due for June 2025
  • July 20 Federal
    Monthly payroll tax deposits due for June 2025
  • July 31 Cook County
    Second installment of Cook County property taxes due
  • Varies Chicago
    Chicago Head Tax return due for qualifying businesses (50+ employees)
August 2025
  • August 15 Chicago
    Chicago Restaurant Tax due for July 2025
  • August 20 Federal
    Monthly payroll tax deposits due for July 2025
  • Varies Chicago
    Chicago business license renewals (based on issue date)
September 2025
  • September 15 Federal & IL
    3rd quarter estimated tax payments due for individuals and businesses
  • September 15 Federal & IL
    Extended S-Corporation and Partnership tax returns due
  • September 15 Chicago
    Chicago Restaurant Tax due for August 2025
  • September 20 Federal
    Monthly payroll tax deposits due for August 2025
  • September 30 IL & Federal
    Quarterly federal and Illinois withholding returns due
October 2025
  • October 15 Federal & IL
    Extended individual and C-Corporation tax returns due
  • October 15 Chicago
    Chicago Restaurant Tax due for September 2025
  • October 20 Federal
    Monthly payroll tax deposits due for September 2025
  • October 31 IL
    Illinois Property Tax Credit claim deadline
November 2025
  • November 15 Chicago
    Chicago Restaurant Tax due for October 2025
  • November 20 Federal
    Monthly payroll tax deposits due for October 2025
  • Varies Chicago
    Chicago business license renewals (based on issue date)
December 2025
  • December 15 Chicago
    Chicago Restaurant Tax due for November 2025
  • December 20 Federal
    Monthly payroll tax deposits due for November 2025
  • December 31 Federal & IL
    Last day for tax-deductible charitable contributions
  • December 31 Federal
    Last day for businesses to establish qualified retirement plans
  • December 31 IL & Federal
    Quarterly federal and Illinois withholding returns due

Chicago-Specific Tax Considerations

In addition to federal and Illinois deadlines, Chicago business owners must be aware of several Chicago-specific tax obligations:

  • Chicago Business License Taxes: Due dates vary based on the issue date of your license
  • Chicago Restaurant Tax: Due on the 15th of each month for the previous month’s sales
  • Chicago Amusement Tax: Typically due monthly or quarterly depending on volume
  • Chicago Personal Property Lease Transaction Tax: Due monthly or annually depending on liability
  • Chicago Head Tax: Due quarterly for businesses with 50+ employees
  • Chicago Hotel Accommodations Tax: Due monthly for applicable businesses

Extension Filing Information

While extensions give you additional time to file your returns, they do not extend the time to pay taxes owed. Chicago taxpayers should be aware of the following extension deadlines:

Individual Tax Filing Extensions

Individual taxpayers can request a six-month extension to file their federal and Illinois state tax returns. The extension request must be filed by the original due date (typically April 15).

  • Federal: Form 4868 extends the filing deadline to October 15, 2025
  • Illinois: IL-505-I extends the filing deadline to October 15, 2025

Important: The extension only applies to filing the return, not paying the tax. Any taxes owed must still be paid by the original due date to avoid penalties and interest.

Quarterly Estimated Tax Payment Schedule

Self-employed individuals, businesses, and those with income not subject to withholding must make quarterly estimated tax payments. For Chicago taxpayers, this includes both federal and Illinois state estimated payments.

Quarter Period Covered Due Date Federal Form Illinois Form
1st Quarter January 1 – March 31, 2025 April 15, 2025 1040-ES IL-1040-ES
2nd Quarter April 1 – May 31, 2025 June 15, 2025 1040-ES IL-1040-ES
3rd Quarter June 1 – August 31, 2025 September 15, 2025 1040-ES IL-1040-ES
4th Quarter September 1 – December 31, 2025 January 15, 2026 1040-ES IL-1040-ES

Chicago Business Owners: Special Considerations

In addition to income tax estimated payments, Chicago business owners should be aware of:

  • Sales Tax Filings: Monthly, quarterly, or annually depending on sales volume
  • Payroll Tax Deposits: Semi-weekly, monthly, or quarterly based on liability
  • Illinois Unemployment Insurance: Quarterly filings and payments
  • Chicago-Specific Tax Filings: Various schedules based on business type

Never Miss a Deadline Again

Staying on top of tax deadlines is crucial for Chicago businesses and individuals. Our tax professionals can help you create a customized tax calendar based on your specific situation, send you timely reminders, and ensure you never miss an important filing date.

Contact us today to schedule a consultation and let us help you develop a comprehensive tax compliance strategy tailored to your Chicago business or personal tax situation.

Schedule a Tax Planning Consultation