Warning on Chicago anchoring
I anchored last year in the harbor near the water treatment plant and found that the bottom is covered with long, slippery grass not the sand you might expect. I held but it created a real problem when retrieving the anchor. Once I had broken the grip on the bottom, the anchor had so much grass on it that it became very heavy and difficult to haul aboard. It was hopeless at that point to reset because of the fouled anchor (it was a Danforth). Remember that the small size of the harbors in Chicago basically always put you near a lee shore. We got underway just short of the breakwall. I've seen others who have not and ended up on the wall. I sail out of Montrose and I ancored quite a bit between Montrose and Belmont on the lake itself. The holding there is very good and clean. Just stay away from the Belmont entrance as it gets quite a bit of wave action due to wakes and rebound off the wall. The harbors downtown are also washing machines because of their small sizes and heavy use.
