Official
Updated 2026-08-09

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

First Day Aug 23, 2027
Last Day Jun 9, 2028
Thanksgiving Holiday Nov 25-26
Winter Vacation Dec 20-31
Spring Vacation Mar 20-24

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

EventDate(s)
Q1 Progress Report Distribution DaySeptember 23, 2027 (Thu)
End of Q1October 22, 2027 (Fri)
Parent-Teacher Conference DayNovember 2, 2027 (Tue)
Q1 Report Card PickupNovember 2, 2027 (Tue)
Q2 Progress Report Distribution DayDecember 10, 2027 (Fri)
End of Q2January 21, 2028 (Fri)
Q2 Report Card Distribution DayJanuary 28, 2028 (Fri)
Q3 Progress Report Distribution DayFebruary 25, 2028 (Fri)
End of Q3March 31, 2028 (Fri)
Parent-Teacher Conference DayApril 13, 2028 (Thu)
Q3 Report Card PickupApril 13, 2028 (Thu)
Q4 Progress Report Distribution DayMay 5, 2028 (Fri)
End of Q4June 9, 2028 (Fri)
Q4 Report Card Distribution DayJune 9, 2028 (Fri)

Chicago Public Schools Calendar 2027-2028 www.illinoisschoolcalendar.com

View the full 2027-2028 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 23, 2027

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.

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 9, 2028

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.

Select at least one nearby district.

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.