The Monroe harbor marina and the Chicago Yacht Club are separate operations, fortunately. I'm not a member of the Chicago Yacht Club - I've heard some things about them that doesn't sound appealing to me anyway, like an initiation fee of $1000 times your age in years and that they are not giving reciprocal rights to visitors.
The tenders are indeed part of the harbor operations and very nice and efficient. Being on a mooring is actually the cheapest and only option for a starter in Chicago, since slips have long waiting lists. Monroe harbor has around 1000 cans! It costs me about $1200 for the season, which includes the tender service fee, taxes and so on. Of course, the season is only 4-5 months here, in fall the harbor closes down and in winter it freezes over for a few months.
I went to see the square rigger I tangled with and looked at their yards - they are actually steel and my mast didn't leave a scratch on them. This square rigger is a great ship with a home port in Nova Scotia. It's a training ship and offers both long and short trips. It's pretty costly, but sounds like a wonderful experience and way to learn your ropes literally.
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