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School Open
Dismissal: 3:30 PM
Next 7 Days
April 2026
Coming Up
School Breaks
Holidays (No School)
The City of Chicago School District 299 school calendar for the 2025-26 school year runs from Monday, August 18, 2025 to Thursday, June 4, 2026 in Illinois.
- •2 scheduled breaks and 9 holidays throughout the year
- •Spring break: Mar 23 – Mar 27
- •Winter break: Dec 22 – Jan 2
City of Chicago School District 299 starts school 171 days earlier than most Illinois districts. Winter break matches the most common Illinois schedule, starting 12/22. Spring break aligns with the most common Illinois schedule.
Download the iCal file above to sync all City of Chicago School District 299 dates with your phone or computer.
Frequently Asked Questions
Is City of Chicago School District 299 school open today?
Yes, City of Chicago School District 299 is open today. Check the weekly calendar above for upcoming school days and closures.
When is the next day off for City of Chicago School District 299?
The next day off is Monday, May 25, 2026 for Memorial Day.
When is the first day of school for City of Chicago School District 299?
The first day of school for City of Chicago School District 299 in 2025-26 is Monday, August 18, 2025.
When is the last day of school for City of Chicago School District 299?
The last day of school for City of Chicago School District 299 in 2025-26 is Thursday, June 4, 2026.
When is spring break for City of Chicago School District 299?
Spring break for City of Chicago School District 299 is Monday, March 23, 2026 to Friday, March 27, 2026.
When is winter break for City of Chicago School District 299?
Winter break for City of Chicago School District 299 is Monday, December 22, 2025 to Friday, January 2, 2026.
When do students go back to school after winter break?
Students in City of Chicago School District 299 return to school after winter break on Monday, January 5, 2026. Winter break ends on Friday, January 2, 2026.
When is Thanksgiving break for City of Chicago School District 299?
Thanksgiving break dates for City of Chicago School District 299 are not yet available.
How do I add City of Chicago School District 299 calendar to my phone?
Click the "Add to Calendar" button at the top of this page to download the iCal (.ics) file. Then:
iPhone/iPad: Tap the downloaded file, then tap "Add All" to add events to your Calendar app.
Android: Open the file with Google Calendar, review the events, and tap "Import".
Google Calendar (web): Go to Settings → Import & Export → Select the .ics file → Import.
Outlook: Double-click the file or drag it into your Outlook calendar.
Apple Calendar (Mac): Double-click the file or go to File → Import → select the .ics file.
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Other Illinois Districts
Last updated: December 19, 2025
Source: City of Chicago School District 299 Official Calendar