Soon after Dennis Kass started teaching history at a small high school in Little Village four years ago, he put his law degree to use, dispensing free legal advice to students and their families after school. That modest beginning has evolved into the Chicago Law and Education Foundation, a free clinic that has now expanded to eight additional city high schools.

Mr. Kass, 35, estimated that he handled about 100 legal cases last year and said the foundation had helped thousands of people by distributing brochures and answering questions at open houses.