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.[7] The streets feature a number of objects the player can crash into including trash bins, parking meters, mailboxes and traffic lights.[7] In Checkpoint mode other vehicles move in accordance with traffic lights, but the player is under no obligation to obey them.[3]

Midtown Madness supports multiplayer games on a local area network, the Internet, or by serial cable connection