Official
Updated 2026-08-09

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

First Day Aug 24, 2026
Last Day Jun 11, 2027
Thanksgiving Holiday Nov 26-27
Winter Vacation Dec 21-Jan 1
Spring Vacation Mar 22-26

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

EventDate(s)
Q1 Progress Report Distribution DaySeptember 24, 2026 (Thu)
End of Q1October 23, 2026 (Fri)
Parent-Teacher Conference DayNovember 2, 2026 (Mon)
Q1 Report Card PickupNovember 2, 2026 (Mon)
Q2 Progress Report Distribution DayDecember 11, 2026 (Fri)
End of Q2January 22, 2027 (Fri)
Q2 Report Card Distribution DayJanuary 28, 2027 (Thu)
Q3 Progress Report Distribution DayFebruary 26, 2027 (Fri)
End of Q3April 2, 2027 (Fri)
Parent-Teacher Conference DayApril 12, 2027 (Mon)
Q3 Report Card PickupApril 12, 2027 (Mon)
Q4 Progress Report Distribution DayMay 6, 2027 (Thu)
End of Q4June 11, 2027 (Fri)
Q4 Report Card Distribution DayJune 11, 2027 (Fri)

Chicago Public Schools Calendar 2026-2027 www.illinoisschoolcalendar.com

View the full 2026-2027 school year by month.

Monthly calendar12 months
School Day
Weekend
Holiday (No School)
School Break
First / Last Day

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.

Later regional start August 24, 2026

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.

Student-only planning days 9 items

Chicago Public Schools lists 9 teacher, planning, or student-holiday items beyond the headline break periods.

Later last day June 11, 2027

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.

Select at least one nearby district.

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.