William,
That was DuSable harbor. Not sure if you plan on coming in by boat or if you plan to trailer and launch. Being from Iowa, I'll assume the latter in which case you probably won't be able to do DuSable. Yeah it's nice but there's no launch or place to park your truck/trailer. Also, it is one of the more exclusive harbors so getting a transient slip may be problematic. I'd suggest Diversey harbor. Unless there's some special event going on, they usually have plenty of trailer parking in the lot. You can try calling the company running the harbors (Westrec?? google it) in advance to reserve a slip but from what I remember, it's not a guaranteed reservation. They assign transients first come-first served to spots where the slip owners have indicated they will be out on a given date. If you plan on leaving the boat in the water you also need to consider where to park your truck and trailer. The lot charges by the day so you have to pony up the $20-$30 each night in addition to the slip fee. Not sure where you plan to plan to stay but I would suggest getting a hotel somewhere downtown near the harbor. That way you can leave the truck and trailer in the harbor lot and just walk/cab to and from the hotel, eats, etc. The area around Diversey harbor is beautiful. Parks, tons of restraunts, bars, even a botanical garden if thats your thing. If you plan to sleep on the boat, they have electric and water. Showers are a quetion mark. I think there are showers at the yacht club but they may not be public. Something to ask when you call to reserve a slip.
Good luck with your trip and pray for 5 knot SW breeze out on the lake!
Paul Baisch