| August 08 | Bud Billiken Day parade |
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| August 10 | First day of school: Track E |
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| August 17 | Proposed 2009-10 budget hearing |
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| August 18 | Proposed 2009-10 budget hearing |
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| August 19 | Proposed 2009-10 budget hearing |
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| August 21 - August 23 | Chicago All-Star Classic |
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| October 01 | Application period begins for magnet schools and programs |
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| October 03 | National College Fair |
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| October 03 | Options for Knowledge Elementary School Fair |
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| October 10 | CPS High School Fair |
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| October 15 | Deadline to submit health forms |
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| October 28 | School Board Meeting |
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| October 29 | Principal for a Day |
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| November 01 | Daylight Saving Time ends |
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| November 06 | End of the first quarter |
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| November 14 | Community meeting |
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| November 16 | Community meeting |
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| November 17 | Community meeting |
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| November 19 | Admissions policy community meeting |
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| November 20 | Admissions policy community meeting |
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| November 21 | Admissions policy community meeting |
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| November 23 | School Board Meeting |
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| November 27 | Prep Bowl |
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| December 16 | Progress report distribution day |
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| December 18 | Application deadline for all magnet schools and programs |
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| February 03 | Report card distribution day |
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| February 24 | School Board Meeting |
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| March 02 - March 12 | Elementary School ISAT testing |
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| March 10 | Progress report distribution day |
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| March 14 | Daylight Saving Time begins |
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| March 24 | School Board Meeting |
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| March 29 | Spring break |
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| April 05 | Classes resume |
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| April 09 | Third quarter ends |
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| April 28 | School Board Meeting |
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| April 28 | High School PSAE Testing |
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| May 15 | Deadline to submit dental forms |
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| May 26 | School Board Meeting |
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| June 18 | Last day of school |
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| June 21 | First day of Summer School |
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| July 04 | Independence Day |
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| July 28 | School Board Meeting |
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| August 25 | School Board Meeting |
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