Share with Parents
Help other parents find this calendar
Weekend
Next 7 Days
October 2026
Coming Up
School Breaks
Holidays (No School)
The City of Chicago School District 299 school calendar for the 2026-27 school year runs from Monday, August 24, 2026 to Friday, June 11, 2027 in Illinois.
- •2 scheduled breaks and 9 holidays throughout the year
- •Spring break: Mar 22 – Mar 26
- •Winter break: Dec 21 – Jan 1
City of Chicago School District 299 starts school 200 days later than most Illinois districts. Winter break starts 364 days later than 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?
No, today is Saturday - school is not in session on weekends.
When is the next day off for City of Chicago School District 299?
The next day off is Monday, October 12, 2026 for Indigenous Peoples’ 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 2026-27 is Monday, August 24, 2026.
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 2026-27 is Friday, June 11, 2027.
When is spring break for City of Chicago School District 299?
Spring break for City of Chicago School District 299 is Monday, March 22, 2027 to Friday, March 26, 2027.
When is winter break for City of Chicago School District 299?
Winter break for City of Chicago School District 299 is Monday, December 21, 2026 to Friday, January 1, 2027.
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 4, 2027. Winter break ends on Friday, January 1, 2027.
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.
Get Calendar Alerts
We'll email you when City of Chicago School District 299 updates their calendar.
Other Illinois Districts
Last updated: September 5, 2026
Source: City of Chicago School District 299 Official Calendar