Midtown Madness is a racing sim created by Angel Studios for Windows and published by Microsoft in 1999.
The game allows you to drive different vehicles in four different single-player modes: Blitz, Circuit, Checkpoint, and Cruise. Five cars/vehicles are immediately available since the beginning, while five more are unlockable when you reach some goals, like getting the top 3 positions in a race.
Vehicles range from the iconic Volkswagen New Beetle to the Ford F-350, a city bus, and a Freightliner Century truck. The best part is that you are not limited to a set of predefined circuits. The game is set in an open world: the city of Chicago recreated in 3D.
Midtown Madness received excellent reviews and represented a milestone in the racing/driving sim genre. Don't miss it.
Remember to play the game inside a virtual machine or set the compatibility mode in Windows 10/11.