For a b'day weekend, I'd skip Crofton - the food is certainly good, but its not the most lively of atmospheres. I'd pick Wave (in the W on Lake Shore Drive) - dets
http://www.waverestaurant.com/default.html - great food & the space is fab as well, plus I love the dessert tasting platter for a group.
If you think your group can manage Asian, I'd also rec Le Colonial or Le Lan (upscale french/vietnamese) - plenty of recognizable seafood/red meat/chicken options with more adventurous items & good cocktails.
Also try Brasserie Jo (59 West Hubbard, 5 min cab ride from your location), Cafe Spiaggia (900 N Michigan, if you're okay adding another Italian meal), & maybe also Bandera (State & Ohio).
(Fun lunch options nearby are RL at Ralph Lauren (dress up) & Tempo (v casual).)