My boss is attending a conference in Chicago at the end of May. Its being held at the Congress Plaza Hotel and while in the city she was planning to check out some of the hotels. She owns a funky,historic hotel in Toronto, Canada and was wondering if there is anything like that in Chicago. Any recommendations?

Try the Monaco.

Allegro, Palmer House Hilton, Talbot?

W Hotels - 172 West Adams or 644 North Lake Shore Drive.

Hotel Burnham sounds like what you're looking for. Another might be the House of Blues...but I would forget the Palmer House.

Heather, would have to agree with some of the postings (W Hotels, Allegro, Monaco), but also would add if she wants funky in older building that she might want to try a cool B&B:

http://www.haymarketinn.com/

It's in an old loft building that was rennovated and is very ecclectic. Suggested it for some friends in on business and they liked not being in an actual hotel for yet another convention.