Checkpoint has players race against others on pre-defined tracks around the city. Other players will attempt to steal the gold. Capture the Gold is a mode where gold is stashed around the city and the player must take it to a hideout. Extra downloadable content was available via Xbox Live to expand the game's original premise. The game supported Xbox Live for online multiplayer gaming, and a split-screen for offline multiplayer. the player works as a pizza deliverer, rental car driver, limo driver, car salesman, stunt driver, police officer and private eye, completing objectives. In the 'Work Undercover' mission mode, in Paris, the player works as a delivery guy, taxi driver, chauffeur, security guard, ambulance driver, police officer, special agent, while in Washington, D.C.

In Checkpoint Races, the player goes through the checkpoints in any order and gets to the finish line before their opponents. In 'Blitz' races, the player goes through all the given checkpoints in any order and races to the finish line before time runs out. In 'Cruise' (free roam) mode, the player can choose the number of pedestrians and amount of traffic, change the weather and season, the time of day and the season, and collect car-specific paint jobs, in a car selected by the user. In single player the player can freely roam, race, or complete objective-based missions. They represent a smaller area than the real life cities, albeit larger than their comparable counterparts in Midtown Madness and Midtown Madness 2. The country capitals of France and the United States, Paris and Washington, D.C., respectively, are available as open world recreations in the game.

Midtown madness online play