In more detail, the game is played over five rounds, with two rounds representing a single day (daytime and nighttime). Each side takes turns playing cards from two decks of action cards. The first deck represents the leadership committees. For the Establishment, this is the Mayor's office, and for the Demonstrators, this is the Yippies. These decks are primarily focused on building/activating card splays and manipulating the board state. The Mayor faction can access the policy tableau with the mandate action, which include activating undercover agents, authorizing tear gas, redeploying the National Guard, and more.

Then both sides alternate playing action cards from their rank-and-file decks: The National Mobilization Committee to End the War in Vietnam (MOBE) on one side, and the Chicago Police Department on the other. These actions are largely moving and confronting units on the map and claiming strategic positions. The Demonstrators may build and activate their street theater splay, which is a set of location specific one-time "mini-objectives" with unique, combinatorial powers.

At the end of every round, a delegate commits a vote to either side. Demonstrators grow in number, the mayor is allocated funds, and whoever controls a majority of critical city areas is awarded exposure points.

Chicago '68 supports 1-4 players in solo, competitive, co-operative, and team play modes. Game duration is 45 minutes per player, with the typical two player duel lasting 60-90 mins.