( also called Midtown Madness: Chicago Edition) is a racing game developed for the Windows by Angel Studios (now Rockstar San Diego) & published by the Microsoft. The demo version was released via download on May 1, 1999, and the completed game was released toward the end of May 1999. 2 sequels followed, with Midtown Madness 2 released in September 2000 &Midtown Madness 3 released in June 2003 for the Xbox.

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The game is set in Chicago & its objective is to win street races and obtain the latest cars. Unlike other racing games that restrict the player to a race track, Midtown Madness offers an open-world recreation of the Chicago. This setting was said to provide “an unprecedented degree of freedom to drive around in a virtual city”. The Players can explore the city via one of the several modes and can determine the weather & traffic conditions for each race. The game supports multiplayer races above a local area network or the Internet. In general, the game received positive reviews from gaming websites.

Gameplay The Midtown Madness Full Game features 4 single-player modes: Blitz, Circuit, Checkpoint & Cruise. In Blitz, the player must swing through three checkpoints and drive to the finish line within the time limit. The Circuit mode curtains off most of a city to resemble race tracks & pits the player against other cars.

The Checkpoint mode combines the features of Blitz & Circuit has the player race against other cars to a destination—but also adds the problem of other traffic, such as police cars & pedestrians. In the Cruise mode, the player can simply explore a city at their own pace. All of these modes except Cruise are divided into missions; completing 1 unlocks the next. Environmental conditions that cross all modes include weather.time of the day & the density of pedestrians, traffic, and police vehicles.

The heads-up display includes, alongside information about the race, a detailed map, but the display can be turned off. The Players start off with five vehicles, and five more are unlockable; the vehicles available range from a Volkswagen Beetle & a Ford F-350 to a city bus & a Freightliner Century truck. Unlocking the vehicles requires completing goals such as placing within the top 3 of any 2 races. If the player has lastly won a certain race mission, they can change the race’s duration & the weather when replaying it. The Checkpoint mode allows the players to also set the frequency of traffic, police cars, and pedestrians.

The game’s city environment is modeled after Chicago, including many of its landmarks, such as ‘L’, the Willis Tower, Wrigley Field, & Soldier Field. Streets feature a number of objects into which the player can crash, including the trash bins, parking meters, mailboxes, and traffic lights.