If your in Monroe Harbor on a Mooring Can, you might be able to leave your sail up all the way to your mooring. There is in gereral a lot of room to manauver in Monroe, just be careful because you have a lot of boat traffic in that harbor.
Any of the other harbors in the Chicago system and I would have my sails down before entering. They are all way to congested and additionally have way to much boat traffic. A 32' boat is not like sailing in on a 420 or a dinghy. And like Merlin said, have them ready to go back up in an emergency.
Courtney is My Hero
If a man is to be obsessed by something, I suppose a boat is as good as anything, perhaps a bit better than most - E.B. White