| June 13 - September 02 | Preschool registration |
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| June 13 - September 02 | Kindergarten registration |
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| September 02 | First day of school |
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| September 20 | GEAP Elementary School Fair |
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| September 24 | School Board Meeting |
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| October 01 | Application period begins for Options for Knowledge schools and programs |
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| October 11 | CPS High School Fair |
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| October 22 | School Board Meeting |
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| October 25 | National College Fair, Navy Pier |
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| October 25 | Elementary School fair for Options for Knowledge schools and programs |
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| October 30 | Principal for a Day |
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| November 12 | Elementary school report card pickup: No classes - Elementary |
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| November 13 | High school report card pickup: No classes - High schools |
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| November 19 | School Board Meeting |
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| November 20 | Military College Fair |
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| November 27 - November 28 | Thanksgiving Holiday |
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| November 28 | Prep Bowl |
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| December 17 | School Board Meeting |
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| December 19 | Application deadline: magnet schools and programs |
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| December 22 - January 02 | Winter Vacation |
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| January 19 | Martin Luther King Jr. holiday |
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| January 23 | Professional Development Day: No classes |
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| January 28 | School Board Meeting |
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| January 31 | New Schools Expo |
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| February 25 | School Board Meeting |
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| March 02 - March 13 | Elementary School ISAT testing |
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| March 19 | Battle of the Books: High school competitionWhitney Young Magnet High School, 211 S. Laflin St The competition brings teams from approximately 40 chapters of Mayor Daley’s Book Club together to test their knowledge of pre-selected books read over the course of the school year.
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| March 25 | School Board Meeting |
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| April 13 - April 17 | Preschool pre-registration |
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| April 13 - April 17 | Kindergarten pre-registration |
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| April 18 - April 25 | Money Smart Week |
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| April 22 | School Board Meeting |
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| April 22 - April 23 | High School PSAE Testing |
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| May 15 | Applications due for End-of-Year Citywide Options ProgramVisit our News section for more information. | |