The game's city environment is modeled after Chicago, including many of its landmarks, such as the 'L', the Sears Tower (then known as the Sears Tower), Wrigley Field, and Soldier Field.
Vehicles can accrue damage from collisions, and can be disabled if excessive damage is accrued, resulting in premature failure of Blitz or Checkpoint races, or several seconds of time lost before the vehicle is immediately restored in Circuit races and Cruise. The Checkpoint mode allows players to set the frequency of traffic, police cars, and pedestrians. If the player has previously won a 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 in any two races.
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 the weather, time of day, 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.