IGN wrote that the game 'doesn't rely heavily on driving authenticity this game's all about fun.' The review also praised the simplicity whereby players can 'pick a real-world car and go'.

Reviews of Midtown Madness were generally positive, with video game critics praising its gameplay. PC Gamer reported that the recreation was mostly accurate, although certain landmarks were moved to enhance gameplay. The development team asked Chicago residents to playtest the game to ensure that the city was recreated faithfully. They ultimately agreed and decided to use Chicago for the setting because the city was featured in several famous car chases from films, including The Blues Brothers. Angel Studios was initially hesitant to accept Microsoft's offer given the magnitude of the proposed undertaking. They proposed their idea to Angel Studios, who had tried to sell Microsoft a 3D vehicle simulator. According to project director Clinton Keith, the concept behind the game came to two Microsoft employees during an attempt to cross a crowded street in Paris. Microsoft planned to publish sequels to racing computer games with the word Madness in the title, including Motocross Madness and Monster Truck Madness. Midtown Madness was one of the first games that Angel Studios developed for the PC. The heads-up display includes, alongside information about the race, a detailed map, but this display can be turned off.

Environmental conditions that traverse all modes include weather (sunny, rainy, cloudy, and snowy), time of day (sunrise, afternoon, sunset, and night-time), and the density of pedestrians, traffic, and police vehicles. All of these modes except Cruise are divided into missions completing one unlocks the next. In the Cruise mode, the player can simply explore the city at their own pace. The Checkpoint mode combines the features of Blitz and Circuit has the player race against other cars to a destinationâbut also adds the complication of other traffic, such as police cars and pedestrians. The Circuit mode curtains off most of the city to resemble race tracks and pits the player against other cars. In Blitz, the player must swing through 3 checkpoints and drive to the finish line within a time limit. Midtown Madness features 4 single-player modes: Blitz, Circuit, Checkpoint, and Cruise.

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