The game played much like other two-dimensional platform games of its time, collecting keys and defeating enemies with a variety of different techniques. The player controls Michael Jordan on a quest to save the rest of the players for an All-Star charity game, who have all been kidnapped. The player attacks enemies using different basketballs, each with its own ability; for example, the freeze ball can freeze the ground and create a slippery surface, the bomb ball makes a large explosion, and so on. The player must find keys throughout the game to unlock different doors and rescue teammates. Michael can also slam dunk for a secondary attack. This is also used to activate powerup baskets and various checkpoints along the way.
GamePro gave the game a positive review. While they acknowledged that the blatant product placement is annoying, and criticized the controls as extremely difficult, they gave the game a positive recommendation based on its varied gameplay and "intense, complex levels."
Michael Jordan: Chaos in the Windy City was named in the top ten worst video games in Nintendo Power magazine (issue 100), which cited the ridiculous concept.