Chicago Public Schools District 299 Calendar 2026-2027
Complete holiday schedule and key dates for Chicago Public Schools District 299 for the 2026-2027 academic year. Official district website
School Year Timeline
Key Dates
| Event | Date(s) | Status |
|---|---|---|
| First Day of School | August 24, 2026 (Mon) | School Opens |
| Labor Day | September 7, 2026 (Mon) | No School |
| Indigenous Peoples’ Day | October 12, 2026 (Mon) | No School |
| General Election observed in lieu of Veterans Day | November 3, 2026 (Tue) | No School |
| Veterans Day | November 11, 2026 (Wed) | No School |
| Thanksgiving Holiday | November 26, 2026 - November 27, 2026 | No School |
| Winter Vacation | December 21, 2026 - January 1, 2027 | No School |
| Martin Luther King Jr. Day | January 18, 2027 (Mon) | No School |
| Presidents’ Day | February 15, 2027 (Mon) | No School |
| Spring Vacation | March 22, 2027 - March 26, 2027 | No School |
| Memorial Day | May 31, 2027 (Mon) | No School |
| Last Day of School | June 11, 2027 (Fri) | School Closes |
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Extended Time Off
| Window | Date(s) | Length |
|---|---|---|
| Thanksgiving Holiday Window | Nov 21–29, 2026Districtwide no-school: Nov 23–27, 2026 · Adjacent weekend: Nov 21–22, 2026; Nov 28–29, 2026 | 9 days |
| Winter Vacation Window | Dec 19, 2026–Jan 4, 2027Districtwide no-school: Dec 21, 2026–Jan 1, 2027; Jan 4, 2027 · Adjacent weekend: Dec 19–20, 2026; Jan 2–3, 2027 | 17 days |
| Spring Vacation Window | Mar 20–28, 2027Districtwide no-school: Mar 22–26, 2027 · Adjacent weekend: Mar 20–21, 2027; Mar 27–28, 2027 | 9 days |
Other Important Dates
| Event | Date(s) |
|---|---|
| Q1 Progress Report Distribution Day | September 24, 2026 (Thu) |
| End of Q1 | October 23, 2026 (Fri) |
| Parent-Teacher Conference Day | November 2, 2026 (Mon) |
| Q1 Report Card Pickup | November 2, 2026 (Mon) |
| Q2 Progress Report Distribution Day | December 11, 2026 (Fri) |
| End of Q2 | January 22, 2027 (Fri) |
| Q2 Report Card Distribution Day | January 28, 2027 (Thu) |
| Q3 Progress Report Distribution Day | February 26, 2027 (Fri) |
| End of Q3 | April 2, 2027 (Fri) |
| Parent-Teacher Conference Day | April 12, 2027 (Mon) |
| Q3 Report Card Pickup | April 12, 2027 (Mon) |
| Q4 Progress Report Distribution Day | May 6, 2027 (Thu) |
| End of Q4 | June 11, 2027 (Fri) |
| Q4 Report Card Distribution Day | June 11, 2027 (Fri) |
Chicago Public Schools Calendar 2026-2027 www.illinoisschoolcalendar.com
View the full 2026-2027 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; Central District 301 (August 12, 2026) and CHSD 218 (August 11, 2026) 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; Central District 301 (May 25, 2027) and CHSD 218 (May 27, 2027) 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 2026-2027 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.