The game supports multiplayer races over a local area network or the Internet. Players can explore the city using one of several modes and can determine the weather and traffic conditions for each race.
This setting was said to provide 'an unprecedented degree of freedom to drive around in a virtual city'. Unlike racing games that restrict the player to a race track, Midtown Madness offers an open world recreation of Chicago. The game is set in Chicago the object is for the player to win street races and obtain new cars. Two sequels followed, with Midtown Madness 2 released in September 2000 and Midtown Madness 3 released in June 2003 for the Xbox. The demo version was released in April 1999. 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.