good live music at Kingston Mines... slightly touristy, but a ton of fun.
the 'Michigan Mile' along Michigan Ave is cool (south of the river lots of tall buildings, and the waterfront park along the lakeshore; north of the river expensive shopping and designer duds - think bloor st).
the circular parking garage is called Marina City... it's an entire complex. the steak house at the bottom is good, but waaaay overpriced (Smith & Wollensky's). shoulda put some more 'a's' in there... waaaaaaaaaaaaaaay overpriced. HOB is next door.
you will have a ton of fun just walking around looking straight up at the architecture. its a very tall city!