Chicago Public Schools District 299 Calendar 2027-2028
Complete holiday schedule and key dates for Chicago Public Schools District 299 for the 2027-2028 academic year. Official district website
School Year Timeline
Key Dates
| Event | Date(s) | Status |
|---|---|---|
| First Day of School | August 23, 2027 (Mon) | School Opens |
| Labor Day | September 6, 2027 (Mon) | No School |
| Indigenous Peoples’ Day | October 11, 2027 (Mon) | No School |
| Veterans Day | November 11, 2027 (Thu) | No School |
| Thanksgiving Holiday | November 25, 2027 - November 26, 2027 | No School |
| Winter Vacation | December 20, 2027 - December 31, 2027 | No School |
| Martin Luther King Jr. Day | January 17, 2028 (Mon) | No School |
| Presidents’ Day | February 21, 2028 (Mon) | No School |
| Spring Vacation | March 20, 2028 - March 24, 2028 | No School |
| Memorial Day | May 29, 2028 (Mon) | No School |
| Last Day of School | June 9, 2028 (Fri) | School Closes |
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Extended Time Off
| Window | Date(s) | Length |
|---|---|---|
| Thanksgiving Holiday Window | Nov 20–28, 2027Districtwide no-school: Nov 22–26, 2027 · Adjacent weekend: Nov 20–21, 2027; Nov 27–28, 2027 | 9 days |
| Winter Vacation Window | Dec 18, 2027–Jan 3, 2028Districtwide no-school: Dec 20–31, 2027; Jan 3, 2028 · Adjacent weekend: Dec 18–19, 2027; Jan 1–2, 2028 | 17 days |
| Presidents’ Day Window | Feb 19–22, 2028Districtwide no-school: Feb 21–22, 2028 · Adjacent weekend: Feb 19–20, 2028 | 4 days |
| Spring Vacation Window | Mar 18–26, 2028Districtwide no-school: Mar 20–24, 2028 · Adjacent weekend: Mar 18–19, 2028; Mar 25–26, 2028 | 9 days |
Other Important Dates
| Event | Date(s) |
|---|---|
| Q1 Progress Report Distribution Day | September 23, 2027 (Thu) |
| End of Q1 | October 22, 2027 (Fri) |
| Parent-Teacher Conference Day | November 2, 2027 (Tue) |
| Q1 Report Card Pickup | November 2, 2027 (Tue) |
| Q2 Progress Report Distribution Day | December 10, 2027 (Fri) |
| End of Q2 | January 21, 2028 (Fri) |
| Q2 Report Card Distribution Day | January 28, 2028 (Fri) |
| Q3 Progress Report Distribution Day | February 25, 2028 (Fri) |
| End of Q3 | March 31, 2028 (Fri) |
| Parent-Teacher Conference Day | April 13, 2028 (Thu) |
| Q3 Report Card Pickup | April 13, 2028 (Thu) |
| Q4 Progress Report Distribution Day | May 5, 2028 (Fri) |
| End of Q4 | June 9, 2028 (Fri) |
| Q4 Report Card Distribution Day | June 9, 2028 (Fri) |
Chicago Public Schools Calendar 2027-2028 www.illinoisschoolcalendar.com
View the full 2027-2028 school year by month.
Monthly calendar12 months
About Chicago Public Schools District 299
Chicago Public Schools gives every city address a guaranteed public-school route. Each address is assigned a neighborhood elementary school and a neighborhood high school, and a family can enroll directly in those neighborhood programs after proving residency. The basic address-based seat does not require a GoCPS application.
GoCPS manages the optional layer. Families use it to apply to elementary magnet, magnet-cluster, open-enrollment, dual-language, and other choice programs, as well as to high-school choice and selective-enrollment programs. Offers depend on the rules, priorities, eligibility requirements, and available seats attached to each program.
The distinction between a school building and a program inside that building is essential. A neighborhood campus may contain its guaranteed neighborhood program alongside one or more application programs. Living in the attendance area secures the neighborhood route, but it does not automatically place a child in every specialized program housed there. A family may also apply to programs at schools outside the assigned neighborhood.
Prekindergarten requires another check: attending a school’s pre-K classroom generally does not establish a guaranteed kindergarten seat outside the child’s assigned neighborhood route unless CPS states a specific exception. Families planning across grade levels should identify the guaranteed school first, then evaluate each optional program by its own admissions and transportation conditions. CPS is one district, yet students can move through it by many separate enrollment pathways.
Compared With Related Districts
Selected highlights from this district calendar and related district calendar pages.
Chicago Public Schools starts on this date; Barrington 220 (August 18, 2027) and District 200 (August 11, 2027) use different first-day dates in the related calendar set.
Chicago Public Schools lists 9 teacher, planning, or student-holiday items beyond the headline break periods.
Chicago Public Schools ends on this date; Barrington 220 (May 30, 2028) and Community Unit School District 200 (May 26, 2028) close on different dates in the related calendar set.
Compare key dates with nearby districts
Choose one or two related districts to line up major planning dates with Chicago Public Schools.
Related Links
About This Calendar
Data Source: Chicago Public Schools 2027-2028 CPS Family Calendar How we verify dates
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.