Drive around the streets of Chicago in a series of races, or just try the various timed challenges! The entire city is recreated, with more landmarks and major streets drivable, complete with pedestrians and traffic cars! Drive your "common" cars like Cadillac Eldorado or Ford Mustang, or go superexotic like Panoz Roadster, or drive a super-though F-350 HD pickup... Or even the Detroit City Bus and/or a Freightliner truck... Lots of variety, lots of scenary to admire, lots of challenges to attempt... And when you get bored, try the multiplayer, including tag, football, cops and robbers, and many more modes.
There is an error when referencing one of the vehicles on the North American (and some European) cover art. (See extra cover art for example.) It states the Classic Ford Mustang Fastback as a "67 Mustang Boss 302". However, the Boss 302 did not enter production until 1969. It is correctly stated what Mustang it is in the game.
In the Netherlands Midtown Madness got sold for the half of the normal retail (like $20) price to see if this could reduce the illegal copying. Afterwards they didn't try this with any other game, so probably it didn't work.