Midtown Madness (also known as Midtown Madness: Chicago Edition) is a 1999 racing game developed by Angel Studios and published by Microsoft for Microsoft Windows. The demo version was released in April 1999. 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; the object is for the player 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". Players can explore the city using 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. Angel Studios developed another video game featuring open-world recreations of cities, Midnight Club: Street Racing.

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