This oughta help. These is so much to do in Chicago that you can’t possibly be bored. One recommendation, if you can, hit the RedHead Piano Bar. Get there early and stay until late. If you get there early you could score a seat at the piano bar. if not, you will want to at least get a table, but standing isn’t bad. Dress nicely and tip well if standing and waitstaff will probably find a seat for you when one frees up. Plenty of hotels nearby and if you want a great Chicago steak the chicago Chop House is only a block from Redhead. Have dinner at 4:30 (no, it won’t be bluehairs, it will be people who want to eat and then party the night away) and then head to Redhead. If you go, tell me what you will be wearing cause I’ll probably be there!