Unless you have no plans of sleeping on your boat I would suggest something with a larger cabin. Its very nice "camping" on the boat especially if you live far from the harbor. You also want something large enough that you feel comfortable taking it on a trips like those. Lake Michigan isnt exempt from flooding either. Lake levels are at record highs right now, and sometimes you will see flooding depending on what direction the wind is going. If you are looking at a Chicago Harbor take note that at Diversey its probably only half full right now. You are limited because of bridge clearance going in and out of the harbor because of high water levels. Don't quote me but I think you only have 8 or 9ft of clearance right now. Because of this the bigger boats cannot get in or out and moved to other harbors. If you get a larger boat with a radar arch 31st harbor might be your only available option.
Keep it as in which harbor in the city? Are there clearance restrictions on Lake Michigan? I would even entertain a slip on the river. I’m more worried about getting the right size boat.
[MENTION=16]PANDA[/MENTION] talks about bridge clearance issues in this post.
and yeah, that's why i was asking which harbor- cuz if this is an issue- that'd be a pickle.