Unlike many racing games, which restrict the player to a race track, Midtown Madness offers an open world recreation of Chicago. This setting was developed by Microsoft and described as offering "an unprecedented degree of freedom to drive around in a virtual city". Players can explore the city via one of several modes, and can determine the weather and traffic conditions for each race. The game supports multiplayer races over a local area network or the Internet.

• Midtown Madness 1: Windows XP Update
• Midtown Madness 1 Archive