The player views the action from an overhead perspective and works to build control over Chicago. Gameplay centers on moving through the city, confronting opposition, and managing the growth of a criminal organization.

Progress depends on taking territory and dealing with threats from rival gangs and the police. The game is structured around repeated encounters and strategic decisions rather than a linear, character-driven adventure. Exact objectives and input behavior can vary by version, so the DOS manual is useful for confirming scenario details.

Prioritize objectives that increase control of the city before taking unnecessary risks. Keep track of rival activity and police pressure, since losing resources during poorly timed confrontations can slow territorial progress.

Because documentation for the DOS release is limited, consult the original manual for any scenario-specific rules before relying on a fixed route or exploit.