Can't say I've had any really memorable ceasar salads in Chicago, except one...and it's been 10+ years (maybe 15?). My stepdad, who passed away 8 years ago, belonged to the Chicago Yacht Club (and he probably stopped being a member at least 4 or 5 years before he passed).
They used to make and toss it table side, and that was always a treat. Their all-you-can-eat seafood buffet (I think it was on Wednesdays) was also pretty incredible: clams casino, oysters rockefeller, crab legs, bisque, (I think there was a gumbo)...they even took a shot at Sushi.
I'm sure I'm forgetting some items, but that was a rare lakeside treat.