I actually think I prefer a mooring ball to a transient slip, just because it saves on cost and we rarely use shorepower or water hook-ups anyway. Plus, we like to get some use out of the dink!
You will love Monroe harbor than.
You will be right in the Heart of Grant Park with Buckingham Fountain and Queens Landing to great you.
The Museum Campus is a short walk away; Michigan Avenue, the Magnificent Mile, Navy Pier Dinning and Entertaining are all an easy cab ride.
Some more to add to the Ports o Call we talked about.
St Joes is a good stop, probably the best Marina here for a Transient is West Basin Marina; City of St. Joseph, Michigan
There are a couple others further upriver and a bit closer to town, but they are past two bridges, the bridges operate on a regular basis. These two are Harbor Isle and Pier 33. A few others dot the river. From West Basin, I believe they run a tram or shuttle to down town, this might be Memorial Day to Labor Day only. Check ahead on that. The town is OK in my opinion, I have seen better and I have seen worse (like Michigan City), but If I remember correct, its not very easy to obtain provision here.
New Buffalo is one of our favorites. The town has grown by leaps and bounds recently, but still a nice quaint stop. The Municipal Marina has very limited slips, I think maybe twenty or so, they take reservations at Michigan CRS Reservation Service
as does West Basin and any other that is part of the Michigan Park System. from the Municipal Marina you simply step off the docks and are a couple of minute walk to small town shopping and dinning. Its a lot like South Haven but on a smaller scale. Its a very nice stop over and provisions can be obtained a few blocks from the Marina.
I'm sure you would enjoy a stay here.
Michigan City; very nice Marina not much of a town. If your wife likes Outlet Malls they have on there, that's about all they have. If you walk the downtown area, you will find half the store fronts boarded up. The other half should be. A couple of restaurants are an easy walk; Maty's and Galvastons. One thing to check out is the Light House Museum right next to the harbor. If Chicago is your choice in destinations, you might want to consider making the crossing from New Buffalo, it only adds about 15 miles to the trip across.
Both Michigan City and New Buffalo can
have problems with shoaling. Be careful, stay in middle and maybe phone ahead for local knowledge.(not sure about current or upcoming status I have not been in either since '06)
Once again, don't hesitate to ask if there is anything else.