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.
Michael Jordan: Chaos in the Windy City did not sell well and was named in the top ten worst video games in Nintendo Power magazine (issue 100); however, it was noted within the issue that the game was not entirely awful, but the concept itself was deemed ridiculous by many and thus was a part of the criticisms of the game itself.
Allgame gave this video game a rating of 2.5 stars out of possible 5 in their overview.