I'm probably too late to reply. The Congress Hotel is supposedly haunted. We stopped for a drink the

I've not heard of any hotels that are rumored to be haunted in the years I've lived here. (And I'd taken Richard Crowe's ghost tour several years ago and he didn't mention hotels, though, evidently, Chicago is stupid with ghosts.)
I've been trying to think of a hotel that might be somewhat interesting, but they all seem fairly characterless. Maybe the Burnham hotel, being in the Daniel Burnham historic landmark (the Reliance Bldg. of 1895) for its architectural significance.
The location of the St. VAlentine's Day Massacre at approx. 2100 N. Clark Street thrifty car rental dubai is now a parking lot for a retirement home, but there are three trees at the site... the center one is the locale of the back wall of the garage where the men were killed, and the brownstones across the street still exist where Capone's "man" waited for the rival gang to show up. The brownstone has a restaurant now at street level - Chicago Oven and Pizza Grinder.
I'm probably too late to reply. The Congress Hotel is supposedly haunted. We stopped for a drink there during the Weird Chicago tour, though thrifty car rental dubai I don't remember the whole story. (That tour would have some of the weird/haunted things you are looking for).
The Intercontinental Hotel is unique to the extent that it has an informal or unlisted tour. If memory serves, thrifty car rental dubai it was previously an atheletic club and has lots of symbolism. Don't have a link handy but you might search for that.