Protesters complied with the city by containing all of the occupation's supplies (including signs, food, and clothing) in carts on the sidewalk.

[9] In late 2011 Occupy Chicago was able to recruit massive crowds of people to embark on protest marches throughout Chicago because its politics were still very inclusive with primarily "left" liberal minded people and communists, socialists, anarchists but also a fair share of libertarians and even a few who identified as conservative.

[10] Seeking to create a permanent, sheltered base, over 175 protesters were arrested under the orders of Chicago's mayor Rahm Emanuel on the morning of October 16 after refusing to take down tents and remaining in Grant Park near Chicago's lakefront after the park's posted closing hours.

[15] Occupy Chicago remained outdoors without an encampment until January 2012 when the organization acquired an indoor space at 500 W. Cermak in the East Pilsen neighborhood.

[19][20] On May 22, 2012, the Tribune Company filed a Uniform Domain Name Dispute Resolution Policy (UDRP) proceeding with the World Intellectual Property Organization (WIPO) alleging OCT acquired the two web domains OccupyChicagoTribune.org and OccupiedChicagoTribune.org "in bad faith" and in order to "divert traffic" from Tribune websites.

[18][21] The Electronic Frontier Foundation wrote a statement in support of OCT, and critiqued UDRP process for not applying locally relevant laws such as fair use and First Amendment within the U.S.[22] In July 2012, the WIPO panel held the Occupied Chicago Tribune's domains to be legitimate, did not mislead the public and did not infringe on the Tribune Company's property.

In their decision they wrote: ... the Occupy Movement is so well known within the relevant area (both parties being from Chicago, Illinois, in the United States) that the Domain Names are not confusingly similar to Complainant's mark.

In a move to bolster law enforcement of the Occupy movement and upcoming G8 and NATO summits, in Chicago, Mayor Rahm Emanuel's recently passed ordinance imposes harsher fines and rules for protests and demonstrations.

"[23] During the NATO summit, federal, state and local law enforcement made any presence of protesters, even at the corners of LaSalle and Jackson light.