Wicker Park is located northwest of the Loop, on the west side of the Kennedy Expressway. It was built up after the Great Chicago Fire, as displaced residents and immigrants from Scandinavia and Germany streamed in. A lot of the original architecture remains. The John Rapp House at 1407 North Hoyne Street, and the Holy Trinity Cathedral at 1121 Levvitt Street were both designed by architect Louis Sullivan, known as the father of modern architecture.
After World War II, white flight and the construction of the Kennedy Expressway fragmented the neighborhood. Poor Hispanics began moving in. Wicker Park hit rock bottom in the 1960s and 70s. It was the original home of the Latin Kings, a brutal drug gang. In the eighties, new investment and an influx of young professionals began to turn things around.
Every major American city has its own hipster enclave, and Chicago's is Wicker Park. Milwaukee Avenue runs diagonally through this charming neighborhood and is lined with boutiques, cafes, restaurants, and nightclubs. Spend a couple hours exploring the interesting shops. There's an excellent used bookstore and plenty of clothing stores. Pop into a cafe for gourmet coffee or tea. This is a good place to spend an afternoon just wandering around and absorbing the local culture.