The crash occurred at about 10:24 p.m. in the inbound lanes of the Kennedy Expressway near Natoma Avenue.
Illinois State Police said three of the vehicles traveled off the roadway, struck a light pole, and became fully engulfed in flames.
The Chicago Fire Department said one person was killed at the scene and another was transported to a hospital.
All lanes of the expressway were closed for hours between Harlem and Nagle avenues overnight and have since reopened.