

Before a race, if the player has previously won the race, they can change the race duration or the weather, which can affect vehicle performance. To unlock the other cars, players must achieve goals such as winning a certain number of races. Players have a choice of up to ten vehicles, although only five are available at the start. In Blitz, the player must reach a destination within a time limit in Circuit, the player races other vehicles in Checkpoint, the game adds the complication of other traffic, such as police cars and pedestrians and in Cruise, the player simply explores the city. Midtown Madness features four single-player modes: Blitz, Circuit, Checkpoint, and Cruise. Reviewers generally praised the gameplay, though some criticized the graphics. Overall, the game received positive reviews from gaming websites. The game supports multi-player races over a local area network or the Internet. Players can explore the city via one of several modes, and can determine the weather and traffic conditions for each race. This setting was developed by Microsoft and described as offering "an unprecedented degree of freedom to drive around in a virtual city". Unlike many racing games, which restrict the player to a race track, Midtown Madness offers an open world recreation of Chicago. Set in Chicago, the goal of Midtown Madness is to win street races and collect new cars.

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.
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A demo version was released via download on February 1, 1999, and the entire game was released on February 27, 1999. Midtown Madness is a racing game developed for Windows by Angel Studios and published by Microsoft.
