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 (normal, rain, clouds, and snow), time of day (sunrise, afternoon, sunset, and night), and the density of pedestrians, traffic, and police officers.

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-it 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 form race tracks and pits the player against other cars. In Blitz, the player must reach three checkpoints and an end destination within a time limit. Midtown Madness features four 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 via download on and the completed game was released toward the end of May 1999. Midtown Madness Download Free Full Game (also known as Midtown Madness: Chicago Edition) is a racing game developed for Windows by Angel Studios (now Rockstar San Diego) and published by Microsoft.

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