Chicago's 2026-27 year runs Monday, August 24, 2026 to Friday, June 11, 2027 (Pre-K starts a day later and finishes a day earlier), with two weeks off at winter vacation and one at spring vacation. What catches parents out is everything in between: six single professional development days scattered from September to April, two parent-teacher conference Mondays that are "non-attendance days for students", and an Election Day holiday observed "in lieu of Veterans Day", so November 11 is a teacher day rather than a holiday and the kids are home either way.
Below is the full CPS family calendar, every dated entry, with the district's wording kept intact — then how to get it onto your phone next to the team schedules.
Source: 2026–2027 CPS Family Calendar, Elementary and High Schools (PDF) and cps.edu/calendar. Last checked November 6, 2026. The family calendar covers CPS elementary and high schools, is stamped "Last Update: 3.5.2026", and was approved by the Chicago Board of Education in February 2026.
Every date below is copied from the district's own published calendar, not estimated. Districts do revise mid-year, so confirm against the source before you book anything around a date.
36 published entries, 18 of them closures or breaks. A single entry can cover a span of days. Labels are the district's wording.
| Date | What the district calls it |
|---|---|
| Aug 17–21, 2026 | Professional development days; day of non-attendance for studentsNo school |
| Mon, Aug 24, 2026 | First day of school for K-12 (full day of school)First / last day |
| Tue, Aug 25, 2026 | First day of school for PreKFirst / last day |
| Mon, Sep 7, 2026 | Labor Day, holidayNo school |
| Thu, Sep 24, 2026 | Progress report distribution day, Q1 |
| Fri, Sep 25, 2026 | Professional development day; day of non-attendance for studentsNo school |
| Mon, Oct 12, 2026 | Indigenous Peoples' Day, holidayNo school |
| Fri, Oct 23, 2026 | End of Quarter 1 |
| Mon, Nov 2, 2026 | Elementary and High School Parent-Teacher Conference Day (ES and HS); non-attendance day for studentsNo school |
| Tue, Nov 3, 2026 | General Election observed in lieu of Veterans Day, holidayNo school |
| Wed, Nov 11, 2026 | Professional development day; day of non-attendance for studentsNo school |
| Nov 26–27, 2026 | Thanksgiving HolidayNo school |
| Fri, Dec 11, 2026 | Progress report distribution day, Q2 |
| Dec 21, 2026 – Jan 1, 2027 | Winter vacation — schools are closedNo school |
| Mon, Jan 4, 2027 | Professional development day; day of non-attendance for studentsNo school |
| Mon, Jan 18, 2027 | Martin Luther King Jr. Day, holidayNo school |
| Fri, Jan 22, 2027 | End of Quarter 2 |
| Thu, Jan 28, 2027 | Report cards for the second quarter sent home |
| Fri, Jan 29, 2027 | Professional development day; day of non-attendance for studentsNo school |
| Mon, Feb 15, 2027 | Presidents' Day, holidayNo school |
| Tue, Feb 23, 2027 | Professional development day; day of non-attendance for studentsNo school |
| Fri, Feb 26, 2027 | Progress report distribution day, Q3 |
| Mar 22–26, 2027 | Spring vacation — schools are closedNo school |
| Fri, Apr 2, 2027 | End of Quarter 3 |
| Tue, Apr 6, 2027 | Professional development day; day of non-attendance for studentsNo school |
| Mon, Apr 12, 2027 | Elementary and High School Parent-Teacher Conference Day (ES and HS); non-attendance day for studentsNo school |
| Thu, May 6, 2027 | Progress report distribution day, Q4 |
| Fri, May 28, 2027 | Earliest date high school graduation ceremonies can be held |
| Mon, May 31, 2027 | Memorial Day, holidayNo school |
| Mon, Jun 7, 2027 | Earliest date elementary graduation ceremonies can be held |
| Thu, Jun 10, 2027 | Last day of school for preschool studentsFirst / last day |
| Fri, Jun 11, 2027 | Last day of school for students (full day); End of Quarter 4; report cards for the fourth quarter sent homeFirst / last day |
| Mon, Jun 14, 2027 | Professional development day; day of non-attendance for students |
| Jun 15–17 and Jun 21–22, 2027 | Emergency day — school in session if student days fall below state requirement |
| Mon, Jul 5, 2027 | Observance Day, holiday (observed holiday for the district offices) |
| Jul 6, 2027 onward | Anticipated Window for Summer Programs — earliest anticipated start date July 6, 2027; may extend into August 2027 |
Monday, November 2, 2026 and Monday, April 12, 2027 are the Elementary and High School Parent-Teacher Conference Days. The calendar says parents "are asked to pick up report cards and conference with teachers after the first and third quarters" and that conference days "are non-attendance days for students". With November 3 a holiday as well, the first one makes a four-day weekend.
The calendar lists them as "August 17–21, September 25, November 11, January 4 and 29, February 23, April 6, and June 14", and shades each one as a "Day of non-attendance for students". The August week falls before the first day and June 14 after the last, which leaves six single days inside the year: a Friday in September, a Wednesday in November, a Monday and a Friday in January, a Tuesday in February and a Tuesday in April.
The holiday list names Tuesday, November 3 as "General Election observed in lieu of Veterans Day". November 11 still has no students in school, but as a professional development day rather than a holiday. The other holidays are Labor Day (September 7), Indigenous Peoples' Day (October 12), Thanksgiving (November 26–27), Martin Luther King Jr. Day (January 18), Presidents' Day (February 15) and Memorial Day (May 31); the calendar adds that "December 25 – January 1 and July 5 are observed holidays for the district offices".
The quarters end October 23, January 22, April 2 and June 11, so the second quarter — and with it the first semester — closes less than three weeks after students return on January 5. The district's February 27, 2026 letter to families explains the reason: with Labor Day falling on September 7, "it would be challenging for our high school students to complete their required number of semester credits before winter break". Progress reports go out September 24, December 11, February 26 and May 6; second- and fourth-quarter report cards are sent home January 28 and June 11. The quarters are 42, 45, 42 and 47 days, 176 in all.
June 15, 16, 17, 21 and 22 are marked E, which the legend defines as "Emergency day-school in session if student days fall below state requirement". If weather or other closures cost the district attendance days, the year extends into those dates. The calendar also sets floors for graduations — high school ceremonies "cannot be held prior to Friday, May 28, 2027" and elementary ceremonies not before Monday, June 7, 2027 — and anticipates summer programs starting no earlier than July 6, 2027.
The quick way: create a free Schedule Caddie account from this page and the 2026-27 calendar above is already on it as your own schedule — the version we verified on November 6, 2026, yours to edit. If CPS revises the calendar later, upload the new version and you see exactly which days changed before approving them.
Doing it yourself, or a different district:
The district publishes this calendar as a document, not a feed you can subscribe to. Schedule Caddie reads that document for you: download the 2026-27 calendar from the district (the source link above), upload it as a PDF, PNG, or JPG up to 10MB, and it pulls out the no-school days, breaks, early releases with their dismissal times, teacher days, and the first and last day of school.
Nothing is saved until you have looked at it. Every day it found shows up as its own row with the date and label, you uncheck what you don't want and fix anything it misread, and only then does it land on your family calendar, color-coded as School so a holiday Monday reads differently from a 4pm practice. Team schedules you have added as calendar links keep refreshing on their own; the school year sits beside them.
Either way it travels like anything else on your Schedule Caddie calendar: subscribe to your Schedule Caddie link in Google Calendar, Apple Calendar, or Outlook and the school days come along.
Add it to my calendarFree account. How the upload and review step work, in detail: school calendars on Schedule Caddie.
Students begin classes on Monday, August 24, 2026 and end on Friday, June 11, 2027; the calendar notes that "both days are full days of school for students". Preschool students begin on Tuesday, August 25, 2026 and end on Thursday, June 10, 2027.
Winter vacation: schools are closed from December 21, 2026 to January 1, 2027, and January 4 is a professional development day with no students, so classes resume Tuesday, January 5. Spring vacation: schools are closed from March 22 to March 26, 2027. Thanksgiving Holiday is Thursday–Friday, November 26–27, 2026.
Yes to both, for different reasons. Tuesday, November 3, 2026 is a holiday, listed as "General Election observed in lieu of Veterans Day". Wednesday, November 11 is a professional development day, a "day of non-attendance for students". Monday, November 2 is also off for students as a Parent-Teacher Conference Day, so students are out Monday and Tuesday that week and again on the Wednesday of the next.
Inside the school year: the professional development days on September 25, November 11, January 4, January 29, February 23 and April 6, and the Parent-Teacher Conference Days on November 2 and April 12. The professional development week of August 17–21 comes before the first day and June 14 comes after the last. The calendar prints no early-dismissal days.
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Chicago Public Schools, Illinois. Schedule Caddie is not affiliated with the district; the calendar above is reproduced from its public website for convenience.
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