School district · Chicago, Illinois, United States
Chicago Public School District 299 calendar 2026/27 and 2027/28 (Illinois)
The next break in Chicago Public School District 299 is Thanksgiving Holiday, from Thursday 26 November 2026 to Friday 27 November 2026 (2 days).
Below are all school holidays for the 2026/27 and 2027/28 school years, with the first and last day of school where known, and the public holidays of the next twelve months. Updated Fri 16 Oct 2026.
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School holidays
School year 2026/27
First day of school: Mon 24 Aug 2026 · Last day of school: Fri 11 Jun 2027
| Holiday | From | To | Days |
|---|---|---|---|
| Labor Day | Mon 7 Sep 2026 | Mon 7 Sep 2026 | 1 |
| Professional development day No school for students | Fri 25 Sep 2026 | Fri 25 Sep 2026 | 1 |
| Indigenous Peoples’ Day | Mon 12 Oct 2026 | Mon 12 Oct 2026 | 1 |
| Parent-Teacher Conference Day No school | Mon 2 Nov 2026 | Mon 2 Nov 2026 | 1 |
| General Election observed in lieu of Veterans Day | Tue 3 Nov 2026 | Tue 3 Nov 2026 | 1 |
| Professional development day No school for students | Wed 11 Nov 2026 | Wed 11 Nov 2026 | 1 |
| Thanksgiving Holiday | Thu 26 Nov 2026 | Fri 27 Nov 2026 | 2 |
| Winter vacation | Mon 21 Dec 2026 | Fri 1 Jan 2027 | 12 |
| Professional development day No school for students | Mon 4 Jan 2027 | Mon 4 Jan 2027 | 1 |
| Martin Luther King Jr. Day | Mon 18 Jan 2027 | Mon 18 Jan 2027 | 1 |
| Professional development day No school for students | Fri 29 Jan 2027 | Fri 29 Jan 2027 | 1 |
| Presidents’ Day | Mon 15 Feb 2027 | Mon 15 Feb 2027 | 1 |
| Professional development day No school for students | Tue 23 Feb 2027 | Tue 23 Feb 2027 | 1 |
| Spring vacation | Mon 22 Mar 2027 | Fri 26 Mar 2027 | 5 |
| Professional development day No school for students | Tue 6 Apr 2027 | Tue 6 Apr 2027 | 1 |
| Parent-Teacher Conference Day No school | Mon 12 Apr 2027 | Mon 12 Apr 2027 | 1 |
| Memorial Day | Mon 31 May 2027 | Mon 31 May 2027 | 1 |
School year 2027/28
First day of school: Mon 23 Aug 2027 · Last day of school: Fri 9 Jun 2028
| Holiday | From | To | Days |
|---|---|---|---|
| Labor Day | Mon 6 Sep 2027 | Mon 6 Sep 2027 | 1 |
| Professional development day No school for students | Fri 24 Sep 2027 | Fri 24 Sep 2027 | 1 |
| Indigenous Peoples’ Day | Mon 11 Oct 2027 | Mon 11 Oct 2027 | 1 |
| Professional development day No school for students | Mon 1 Nov 2027 | Mon 1 Nov 2027 | 1 |
| Parent-Teacher Conference Day No school | Tue 2 Nov 2027 | Tue 2 Nov 2027 | 1 |
| Veterans Day | Thu 11 Nov 2027 | Thu 11 Nov 2027 | 1 |
| Thanksgiving Holiday | Thu 25 Nov 2027 | Fri 26 Nov 2027 | 2 |
| Winter vacation | Mon 20 Dec 2027 | Fri 31 Dec 2027 | 12 |
| Professional development day No school for students | Mon 3 Jan 2028 | Mon 3 Jan 2028 | 1 |
| Martin Luther King Jr. Day | Mon 17 Jan 2028 | Mon 17 Jan 2028 | 1 |
| Professional development day No school for students | Fri 28 Jan 2028 | Fri 28 Jan 2028 | 1 |
| Presidents’ Day | Mon 21 Feb 2028 | Mon 21 Feb 2028 | 1 |
| Professional development day No school for students | Tue 22 Feb 2028 | Tue 22 Feb 2028 | 1 |
| Spring vacation | Mon 20 Mar 2028 | Fri 24 Mar 2028 | 5 |
| Parent-Teacher Conference Day No school | Thu 13 Apr 2028 | Thu 13 Apr 2028 | 1 |
| Professional development day No school for students | Fri 14 Apr 2028 | Fri 14 Apr 2028 | 1 |
| Memorial Day | Mon 29 May 2028 | Mon 29 May 2028 | 1 |
Public holidays in Illinois, next 12 months
| Date | Holiday |
|---|---|
| Tue 3 Nov 2026 | Election Day |
| Wed 11 Nov 2026 | Veterans Day |
| Thu 26 Nov 2026 | Thanksgiving Day |
| Fri 25 Dec 2026 | Christmas Day |
| Fri 1 Jan 2027 | New Year's Day |
| Mon 18 Jan 2027 | Martin Luther King Jr. Day |
| Fri 12 Feb 2027 | Lincoln's Birthday |
| Mon 15 Feb 2027 | Washington's Birthday |
| Mon 1 Mar 2027 | Casimir Pulaski Day |
| Mon 31 May 2027 | Memorial Day |
| Fri 18 Jun 2027 | Juneteenth National Independence Day Observed |
| Sat 19 Jun 2027 | Juneteenth National Independence Day |
| Sun 4 Jul 2027 | Independence Day |
| Mon 5 Jul 2027 | Independence Day Observed |
| Mon 6 Sep 2027 | Labor Day |
| Mon 11 Oct 2027 | Columbus Day |
Frequently asked questions
When is Thanksgiving Holiday 2026 in Chicago Public School District 299?
Thanksgiving Holiday 2026 in Chicago Public School District 299 is from Thursday 26 November 2026 to Friday 27 November 2026, 2 days including weekends.
When is Winter vacation 2026 in Chicago Public School District 299?
Winter vacation 2026 in Chicago Public School District 299 is from Monday 21 December 2026 to Friday 1 January 2027, 12 days including weekends.
When is Spring vacation 2027 in Chicago Public School District 299?
Spring vacation 2027 in Chicago Public School District 299 is from Monday 22 March 2027 to Friday 26 March 2027, 5 days including weekends.
When is the last day of school in Chicago Public School District 299?
The last day of the 2026/27 school year is Friday 11 June 2027.
When is Thanksgiving Holiday 2027 in Chicago Public School District 299?
Thanksgiving Holiday 2027 in Chicago Public School District 299 is from Thursday 25 November 2027 to Friday 26 November 2027, 2 days including weekends.
When does school start in Chicago Public School District 299?
The first day of school for 2027/28 is Monday 23 August 2027.
When is the last day of school in Chicago Public School District 299?
The last day of the 2027/28 school year is Friday 9 June 2028.
Can I add the Chicago Public School District 299 school holidays to my calendar?
Yes. Subscribe to the free calendar feed https://api.holibase.org/v1/school-holidays/US.ics?authority=712ed341-c36c-5794-8571-8d0fce39d06a&lang=en in Apple Calendar, Google Calendar or Outlook. It updates by itself.
Sources
| School year | Source | Document | Checked |
|---|---|---|---|
| 2026/27 | Researched by Holibase | www.cps.edu | Fri 16 Oct 2026 |
| 2027/28 | Researched by Holibase | cdn.bfldr.com | Fri 16 Oct 2026 |
Public holidays © python-holidays contributors (MIT). School calendars © Holibase contributors (CC BY 4.0). Schools can change their calendar; for important decisions, confirm with the school or authority. Report a mistake.