I think Kurt Elling is playing (singing, actually) somewhere in Chicago on Valentine's Day, but I forget where. He has a web site (if you're interested in his stuff), I'm sure it's on there. I saw him when he jumped up on stage with Benny Golson a few weeks ago at the Jazz Showcase; this was the first time I had actually heard him. He was pretty good, but I don't have any of his recording to really know what he's all about!
The Judy Roberts Trio and Two for Brazil are playing at the Jazz Showcase on V-Day also. I don't know too much about either.
Mark