Just came back from our Chicago River trip. Had a good time. So, since I couldn't find many pointers here or in other links, I'll add some!
Wise decision to launch down river, rather than on the Lake. No worry's about wind driven lake chop or large waves to deal with. While we launched on the Des Plaines river at Three Rivers Marina in Wilmington IL, which allowed us very reasonable fee'd safe parking and a ramp, we did see several marinas and ramps along the Calumet River as we returned. One in particular was Howes Landing of Cook County. However, I don't know if overnight parking there is permitted or what their safety is. Also saw several marinas with ramps between Calumet Harbor and the OBrien Lock, but again, not sure about costs for parking and launching.
DuSable Harbor, as with all the Chicago harbors was pretty pricey, at $85/night for the CD-22. I had made reservations a week or so in advance, and it didn't appear to have very many open slips when we were there. I wasn't overly impressed with the bathroom/shower facilities for the price they charge, but they suffice.
River gets busier in the evenings. I can't speak for the weekend as we were there Thursday and Friday. There are no restaurants with cheap docking available. $25 an hour was about the cheapest we found. Really no dockage available upstream of where we launched. We did stay one night on the concrete wall in Joliet. Felt safe right across the river from the police station, and relatively calm. The barge wakes are pretty light as they are going thru pretty slow due to the bridges very close by. However, that does present a noise problem, as the bridges blow a siren before opening, and are pretty noisy in closing. The wake problems tend to be from any passing pleasure craft. Also, the concrete wall is about 3 feet higher than our gunnel, and is crumbling. However, there are electrical boxes so one can plug in for free. There is no charge for staying on the wall there. Beyond that, there are a few marinas in Chicago, but not sure if they offer transiet slips.
Locks monitor and use ch. 14. (Except the Obrien Lock on the Cal-Sag monitors 16.) Most the tugs are monitoring 16 also. The Chicago locks use lines hanging over the side, however the other locks have you tie up to Bollards. With the high Lake levels right now, the Chicago lock drops you about 3 or 4 feet from lakeside to river. The locks on the rivers seem to have about a 40 foot lift or drop.
Enjoyable cruise, but plan on possible delays of up to 4 hours at the locks. (Chicago lock routinely didn't seem to be more than 15-30 minutes, as they are mostly dealing with Pleasure Craft of the tour boats.) Our longest waits were at the Brandon Road Lock, both ways, with about a 2 hour delay the first time, and close to 3 hours the second time.
We were able to make the 150 statue miles (from 3 rivers, it's about 52 miles, but we also did some extra cruising on the river while there, and also a 10 mile run from Du Sable down to Calumet) on 39 gals of gas. (So pretty much our total fuel load.) There is no fuel between the marinas at 3 Rivers, until Chicago. Or if going via the Cal Sag, until you get close to Chicago.