Midtown Madness (also known as Midtown Madness: Chicago Edition) is a racing game developed for Windows by Angel Studios (now Rockstar San Diego) and published by Microsoft. The demo version was released via download on May 1, 1999 and the completed game was released toward the end of May 1999.[1] Two sequels followed, with Midtown Madness 2 released in September 2000 and Midtown Madness 3 released in June 2003 for the Xbox. The game is set in Chicago and its objective is to win street races and obtain new cars.

Unlike racing games that restrict the player to a race track, Midtown Madness offers an open world recreation of Chicago. This setting was said to provide "an unprecedented degree of freedom to drive around in a virtual city".[2] Players can explore the city via one of several modes, and can determine the weather and traffic conditions for each race. The game supports multiplayer races over a local area network or the Internet. The game received generally positive reviews from gaming websites.[3]