Players start off with 5 vehicles, and 5 more are unlockable the vehicles available range from a Volkswagen New Beetle and a Ford F-350 to a city bus and a Freightliner Century truck. The heads-up display includes, alongside information about the race, a detailed map, but this display can be turned off. Environmental conditions that traverse all modes include weather (sunny, rainy, cloudy, and snowy), time of day (sunrise, afternoon, sunset, and night-time), and the density of pedestrians, traffic, and police vehicles. All of these modes except Cruise are divided into missions completing one unlocks the next. In the Cruise mode, the player can simply explore the city at their own pace. The Checkpoint mode combines the features of Blitz and Circuit has the player race against other cars to a destination-but also adds the complication of other traffic, such as police cars and pedestrians. The Circuit mode curtains off most of the city to resemble race tracks and pits the player against other cars. In Blitz, the player must swing through 3 checkpoints and drive to the finish line within a time limit.

Midtown Madness features 4 single-player modes: Blitz, Circuit, Checkpoint, and Cruise. The game received generally positive reviews from gaming websites. The game supports multiplayer 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 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 and its objective is 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 on April 30, 1999.

Midtown Madness (also known as Midtown Madness: Chicago Edition) is a racing game developed for Windows by Angel Studios and published by Microsoft.

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