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Multiplayer mode includes a Cops and Robbers mode, a capture the flag-style game in which players form two teams and each team tries to steal the opposing team's cache of gold and return it to their own hideout.

It is now supported by similar services such as GameSpy Arcade and XFire, via DirectPlay. Multiplayer mode was originally supported by Microsoft's MSN Gaming Zone, but this service was retired on June 19, 2006.

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Midtown Madness supports multiplayer games via local area network, Internet, or serial cable connection. In Checkpoint, other vehicles move in accordance with traffic lights, but the player is under no obligation to obey them. The streets feature a number of objects into which the player can crash, including trash bins, parking meters, mailboxes, and traffic lights. The game's city environment is modeled after Chicago, including many of its landmarks, such as the 'L', the Willis Tower (then known as the Sears Tower), Wrigley Field, and Soldier Field. The Checkpoint mode allows players to also set the frequency of traffic, police cars, and pedestrians. If the player has previously won a certain race mission, they can change the race's duration and the weather when replaying it. Unlocking vehicles requires completing goals such as placing within the top three of any two races. Players start off with five vehicles, and five more are unlockable the vehicles available range from a Volkswagen Beetle and a Ford F-350 to a city transit 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 (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 В«an unprecedented degree of freedom to drive around in a virtual cityВ». 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.

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The demo version was released via download on and the completed game was released toward the end of May 1999.

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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.