The available vehicles range from a Volkswagen New Beetle and a Ford F-350 to a city bus and a Freightliner Century truck. Players start off with five vehicles five more are unlockable.

The heads-up display includes information about the race and a detailed map, but this display can be turned off. Environmental conditions found in each mode 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. Each mode except Cruise is divided into missions-completing one unlocks the next. In Cruise mode, the player can simply explore the city at their own pace.

Checkpoint mode combines the features of Blitz and Circuit modes and has the player race against other cars to a destination-but also adds the complication of other traffic, such as police cars and pedestrians. Circuit mode curtains off most of the city to resemble race tracks and pits the player against other cars. In Blitz mode, the player must swing through three checkpoints and drive to the finish line within a time limit. Midtown Madness features four single-player modes: Blitz, Circuit, Checkpoint, and Cruise. Angel Studios developed another video game featuring open-world recreations of cities, Midnight Club: Street Racing. 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 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.

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