House of Blues Hotel, or the Hard Rock are both very unique. The W hotel is cool also.

As far as things to do - don't miss Navy Pier. You can take a ride on the Windy or Windy II around the lakefront - it's a tall ship. Then back on Navy Pier you can take a ride on the Ferris wheel for the view. There are several restaurants - a seafood place (Bubba Gumps) that I've never eaten at and one of my favorites - Joe's Be-Bop which has live Jazz bands. The beer garden on the pier is also a lot of fun, with live bands.

Marguerite in Chicagoland