Alderman David Moore, with the 17th Ward, has been on 73rd Place since Friday.
Moore has described the block as an open air drug market.
He chronicled his stay on a Facebook Live, which was interrupted by gunfire over the weekend.
Several rounds of gunfire could be heard on the video.
Moore said he plans to remain on that block until police offer a clear strategy for ending the drug dealing there.
Over 70 were shot, nine fatally, from Friday to Monday in Chicago.
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