If you want to do a quick overnight cruise; Saturday to Sunday, and you are stuck on launching out of Waukegan, You can look into;
Waukegan to Winthrop Harbor.
Waukegan to Kenosha.
Waukegan to Racine.
I liked Racine a lot the last time we were there.
Also, if you are trailering, why not drive a little further and get away from Waukegan? As you can tell, I am not real big fan of that town. You might find it more enjoyable to launch from Winthrop Harbor or Racine. Just my opinion.
If it were me, I would launch at Winthrop and cruise to Racine; If the weather window was appropriate. I would have to check the charts again, but I belive thats about 25NM's.
Also, you can launch in Chicago if you really want to go there.
Most people use the ramps at Burnham. I am retreiving a friends boat from there next week. We regularly use the ramps there for small sail boats.
Just don't go there on a Sunday when the Bears are in town.
Courtney is My Hero
If a man is to be obsessed by something, I suppose a boat is as good as anything, perhaps a bit better than most - E.B. White