Pros
Working with the students of Chicago Public Schools can be an incredibly rewarding experience. You get to work with a diverse student body that represents a broad swathe of America. Students are frequently excited about learning, and are eager to learn more. Many of the teachers and school employees are wonderful, supportive colleagues. Pay for starting teachers is high, and the health benefits are quite good. Furthermore, Chicago is a beautiful, vibrant community in which to live, with a lot of cultural opportunities, ranging from excellent museums, to extensive libraries, to an excellent opera house, to diverse restaurants, to a strong theater and comedy scene.
Cons
The classrooms can be extremely overcrowded. Over-crowding can result in discipline problems. Also, teachers often do not have ready access to their contracts at the start of every school year, so they work without knowing when their contracts are being violated. There is a strong focus on raising test scores, to the point that innovation by new teachers can sometimes be discouraged. Current teaching theories are sometimes ignored. Probationary teachers and tenured teachers are sometimes judged by very different standards. Also, Chicago in the winter can be quite dismal, especially on days when you have to shovel your car out from under a snowdrift.