2027–2028
OfficialUpdated

Chicago Public Schools District 299 School Calendar 2027-2028

Chicago Public Schools District 299 School Calendar Includes all holidays, breaks, half days, and important dates from August 2027 through June 2028. Dates are manually collected and screened from district-published calendar materials. Printable PDF and Google/Apple Calendar sync options are available below.

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School Year Timeline

School Year at a Glance

  1. First Day of SchoolAug 23, 2027
  2. Thanksgiving BreakNov 25, 2027 - Nov 26, 2027
  3. Winter BreakDec 20, 2027 - Dec 31, 2027
  4. Spring BreakMar 20, 2028 - Mar 24, 2028
  5. Last Day of SchoolJun 9, 2028

School year dates

Key Dates

Key dates for Chicago Public Schools District 299 2027-2028 school calendar
EventDate(s)Status
First Day of School (K-12)
Full school day
First Day of Preschool
First preschool day
Labor Day
No classes
Indigenous Peoples’ Day
No classes
Veterans Day
No classes
Thanksgiving Holiday through
No classes
Winter Vacation through
Schools closed
Martin Luther King Jr. Day
No classes
Presidents’ Day
No classes
Spring Vacation through
Schools closed
Memorial Day
No classes
Last Day of Preschool
Last preschool day
Last Day of School / Quarter 4 Ends / Report Cards
Full school day
Spot an error? Help us keep this calendar accurate.

Extended Time Off

Extended no-school periods for Chicago Public Schools District 299 2027-2028

Continuous planning windows, including adjacent weekends
PeriodDate(s)Length
Professional Development — No Student Classes WindowOct 30 – Nov 2, 2027

Districtwide no-school: Nov 1 – 2, 2027

Adjacent weekend: Oct 30 – 31, 2027

4 days
No Classes Before Thanksgiving WindowNov 20 – 28, 2027

Districtwide no-school: Nov 22 – 26, 2027

Adjacent weekend: Nov 20 – 21, 2027 · Nov 27 – 28, 2027

9 days
Winter Vacation WindowDec 18, 2027 – Jan 3, 2028

Districtwide no-school: Dec 20 – 31, 2027 · Jan 3, 2028

Adjacent weekend: Dec 18 – 19, 2027 · Jan 1 – 2, 2028

17 days
Presidents’ Day WindowFeb 19 – 22, 2028

Districtwide no-school: Feb 21 – 22, 2028

Adjacent weekend: Feb 19 – 20, 2028

4 days
Spring Vacation WindowMar 18 – 26, 2028

Districtwide no-school: Mar 20 – 24, 2028

Adjacent weekend: Mar 18 – 19, 2028 · Mar 25 – 26, 2028

9 days
Parent-Teacher Conferences / Quarter 3 Report Cards WindowApr 13 – 16, 2028

Districtwide no-school: Apr 13 – 14, 2028

Adjacent weekend: Apr 15 – 16, 2028

4 days

Planning windows include weekends; they are not counts of school days missed. Conditional and grade-specific closures are excluded.

For students and families

Other Important Dates

Other important dates for Chicago Public Schools District 299 2027-2028
EventDate(s)
Quarter 1 Progress Reports
End of Quarter 1
Parent-Teacher Conferences / Quarter 1 Report Cards
Quarter 2 Progress Reports
End of Quarter 2
Professional Development / Quarter 2 Report Cards
Quarter 3 Progress Reports
End of Quarter 3
Parent-Teacher Conferences / Quarter 3 Report Cards
Quarter 4 Progress Reports
High School Graduations May Begin — High school graduating students
Elementary School Graduations May Begin — Elementary school graduating students
Grading Period Ends / Report Cards — Kindergarten through grade 12

Month by month

Monthly Calendar

Highlighted dates follow the published calendar; grouped or inferred entries are labelled. Today is determined in Central Time (America/Chicago).

  • School Day
  • Weekend
  • Holiday (No School)
  • School Break
  • First / Last Day

August 2027

Sun
Mon
Tue
Wed
Thu
Fri
Sat
  • First Day of School (K-12)
  • First Day of Preschool

September 2027

Sun
Mon
Tue
Wed
Thu
Fri
Sat
  • Labor Day
  • Quarter 1 Progress Reports
  • Professional Development — No Student Classes

October 2027

Sun
Mon
Tue
Wed
Thu
Fri
Sat
  • Indigenous Peoples’ Day
  • End of Quarter 1

November 2027

Sun
Mon
Tue
Wed
Thu
Fri
Sat
  • Professional Development — No Student Classes
  • Parent-Teacher Conferences / Quarter 1 Report Cards
  • Report Cards
  • Veterans Day
  • No Classes Before Thanksgiving Calculated from calendar
  • Thanksgiving Holiday

December 2027

Sun
Mon
Tue
Wed
Thu
Fri
Sat
  • Quarter 2 Progress Reports
  • Winter Vacation

January 2028

Sun
Mon
Tue
Wed
Thu
Fri
Sat
  • Professional Development — No Student Classes
  • Martin Luther King Jr. Day
  • End of Quarter 2
  • Professional Development / Quarter 2 Report Cards
  • Report Cards

February 2028

Sun
Mon
Tue
Wed
Thu
Fri
Sat
  • Presidents’ Day
  • Professional Development — No Student Classes
  • Quarter 3 Progress Reports

March 2028

Sun
Mon
Tue
Wed
Thu
Fri
Sat
  • Spring Vacation
  • End of Quarter 3

April 2028

Sun
Mon
Tue
Wed
Thu
Fri
Sat
  • Parent-Teacher Conferences / Quarter 3 Report Cards
  • Report Cards
  • Professional Development — No Student Classes

May 2028

Sun
Mon
Tue
Wed
Thu
Fri
Sat
  • Quarter 4 Progress Reports
  • High School Graduations May Begin
  • Memorial Day

June 2028

Sun
Mon
Tue
Wed
Thu
Fri
Sat
  • Elementary School Graduations May Begin
  • Last Day of Preschool
  • Grading Period Ends / Report Cards
  • Last Day of School / Quarter 4 Ends / Report Cards

About Chicago Public Schools District 299

Students have no classes on November 1–2, 2027: Monday is a professional development day, and Tuesday is reserved for parent-teacher conferences. April 13–14, 2028, follows a similar pattern, with conferences on Thursday and staff development on Friday. CPS also marks April 13 for Local School Council elections. Check with your school for conference times and election details.

Students have Thanksgiving week, November 22–26, off. Winter vacation runs December 20–31, but January 3 is a professional development day, so classes resume Tuesday, January 4. Quarter 2 ends January 21. CPS lists second-quarter report-card distribution for January 28, which is also a no-class day; families should ask their schools how report cards will be sent home. Spring vacation is March 20–24, with classes resuming March 27.

K–12 students begin August 23, 2027, and finish June 9, 2028, with full school days at both ends. Pre-K starts August 24 and finishes June 8. High school graduation ceremonies may begin May 26, while elementary ceremonies may begin June 5, depending on each school's schedule. CPS reserves June 13–16 and June 20 as possible emergency attendance days. June 19 is the Juneteenth holiday, not an emergency make-up date.

About This Calendar

Data source: Based on the district calendar and supporting sources listed below.

Disclaimer: This website is not affiliated with Chicago Public Schools District 299, any state education authority, or any official district body. While we strive for accuracy, always verify important dates with the official district website.

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