I read your request and it piqued my interest as I boat on the upper Mississippi (mile 535 +100/-60 so far) this year. The river gets better as you go north. If you ever have the opportunity, I would recommend a trip up to the Twin City's and up the St.Croix. It is a beautiful trip The downside, and one that precludes most cruisers, is the fact that it's a little over 600 miles from the TC,s to the confluence with the Illinois River, From your description I assume your passing thru Chicago on the Sanitary Canal (not named for being clean) to the Illinois and Mississippi. Are you going down the Mississippi or the TennTom? I have passed thru Chicago to the Illinois once and I can't say I would do it again unless it was between where I was and where I wanted to be. I have run the Mississippi from the Ohio north. My experience was the river below the Illinois was a nasty, big, swift, driftwood filled drainage ditch with the addition of lots of commercial traffic, and nearly no pleasure boat facilities. Exception: Alton Marina, just below the Illinois is First Class. If you go down the Miss to the Gulf I have heard it isn't bad If you exit the big river at the Atchafalaya. Memphis and Vicksburg are supposed to Fantastic. I haven't done tha trip myself. I'm going to do the winter blocked on the hard under shrinkwrap, I'm jealous of your plans.