I have been on The Chain O Lakes in NW Illinois since 1985. Be glad to show you around if desired. I will tell you that it is very shallow in some spots and I know where not to go.And the water is muddy since it is a silt bottom. The up side is no issue with rough water, lots of bars and restaurants. And a few sand bars to hit that are fun to anchor at. I have a 36 ft boat if that eases your fear of hitting something.

Don't forget to tell him about the use permit he will need to buy just to use the chain, not to mention that it is crawling with cops!

Go past Chicago and get on 131 northbound in Michigan and visit Traverse City, Charlevoix or Torch Lake.

It's usually the second weekend in August I believe. Usually don't get all the event dates for the season till spring. There might be something online already but I never checked as its a word of mouth thing around here.

I'd like to do the Chicago river at night. What time do they stop operating the locks on the weekend?

So no pulling up on any sand bars huh?

No sandbars on Lake Michigan that I know of.
You`d enjoy Racine, its my new favorite place and even if the lake is ugly its only a 5 minutes to a protected cove.

There are no sand bars around Chicago. Its 20-30 feet deep everywhere...about 15 or 20 miles out. If you get a nice day on the lake (which DOES happen pretty often in the summer when there's a south wind)...you can run out to Boater's Beach in Portage, IN. Gorgeous beaches on the Indiana Dunes National Lakeshore.

Downtown at night is pretty cool...but there's not really any place to go, with the exception of one restaurant/bar right on the main channel...but you are pretty exposed to the wakes from all the ferryboats, and they are ruthless. I don't know that they stop the locks? Latest I've left the city has been midnight or so with no problem...

I used to come thru the downtown locks at wee hours of the night/morning when I rack stored downtown . I don't think they shut them down? Pretty sure they are man'd 24/7.