| 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 27 | 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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| January 28 | School Board Meeting |
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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 25 | School Board Meeting |
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| April 01 | Elementary school report card pickup: No classes - Elementary |
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| April 02 | High school report card pickup: No classes - High schools |
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| April 06 - April 10 | Spring Break |
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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 22 | School Board Meeting |
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| April 23 - April 24 | High School PSAE Testing |
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| May 27 | School Board Meeting |
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| June 12 | Last day of school |
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| June 15 | First day of Summer School |
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| June 24 | School Board Meeting | |