Catalyst Chicago is a newsmagazine dedicated to documenting, analyzing and supporting school-improvement efforts in the Chicago Public Schools.  It is published by the Community Renewal Society.
The Chicago Tribune maintains an education page and other local papers run frequent stories on educational topics.
The Chicago Reporter, one of the city’s premier investigative reporting outfits, follows developments in Chicago Public Schools quite closely.  It has compiled a fantastic archive of all its recent articles on the subject.
District 299 is an active blog concerned exclusively with issues relevant to the Chicago Public Schools.
Teach and Learn is a web page periodically published by Michael Lach, the Director of Science for the Chicago Public Schools.  It is concerned with math and science education and urban school reform.
Mike Klonsky’s Small Talk is another active blog concerning issues of urban school reform, with a special focus on Chicago.
Chicago Public Schools maintains a web page concerning the operation of the local school system.
The Consortium on Chicago School Research at the University of Chicago was formed in 1990 in the aftermath of the Chicago School Reform Act.  It is dedicated to the study of the Chicago Public School system and annually surveys CPS students about the quality of their education.  It also publishes quantitative data about the CPS system and individual CPS schools.
Designs For Change is a three-decades-old educational research and reform organization dedicated to serving as a catalyst for major improvements in public schools in the 50 largest cities in the country, particularly Chicago.
The University of Chicago’s Center for Urban School Improvement runs both the North Kenwood/Oakland and Donoghue charter schools.