Midtown Madness is a racing game developed for Windows by Angel Studios and published by Microsoft. A demo version was released via download on February 1, 1999, and the entire game was released on February 27, 1999. A sequel, Midtown Madness 2, was released in April 2000, and the final addition to the series, Midtown Madness 3 was released in June 2002 for the Xbox. Set in Chicago, the goal of Midtown Madness is to win street races and obtain new cars.
Unlike many racing games, which restrict the player to a race track, Midtown Madness offers an open world recreation of Chicago. This setting was developed by Microsoft and described as offering "an unprecedented degree of freedom to drive around in a virtual city". 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. Overall, the game received positive reviews from gaming websites; reviewers generally praised the gameplay, though some criticized the graphics.