You do realize there is no such thing as "haunted" don't you?

Perhaps you might clarify what else you mean by unusual? A boat hotel? And ancient, run-down hotel? Or???

HI, dowab.

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.

Good luck in your search. Hope you have a good time in Chicago!

At the north end of the Magnificent Mile the Drake is reputed by some to be haunted. http://supernaturaloccurrencestudies.blogspot.com/2010/02/illinois-most-haunted-drake-hotel.html
I could never afford to stay there.

Are there some old speakeasies or places where Al Capone used to hide?

Hi, GreatVacations.

The GReen Mill is a gorgeous old club with connections to Capone.

http://www.weirdchicago.com/greenmill.html

The location of the St. VAlentine's Day Massacre at approx. 2100 N. Clark Street 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.

Otherwise, there is an Untouchables Tour that brings folks around the city.
http://www.gangstertour.com/

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 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, it was previously an atheletic club and has lots of symbolism. Don't have a link handy but you might search for that.

For what it's worth, you're crossing a picket line if you stay there.

andrew, please explain. thx.