Mrs. Machaca and I will be in Chicago next week -- we need to plan Thursday, Friday, Saturday dinners, with different requirements for each.
Thursday is just me and Mrs. M, willing to spend for a great meal. If Alinea hadn't been booked, we'd go there. Reading posts here, we were considering Avenues, Moto, maybe Blackbird on the more casual end. Is Moto worth doing if you don't spend 7 hours there? Are they receptive to dietary resrictions? (My wife is vegetarian + fish.) Same questions for Avenues since I'd probably want the tasting menu there.
Friday is with friends from work, will try to keep the price a little more reasonable. Thinking of Avec if we don't go to Blackbird the night before, or Green Zebra, or Cafe Spiaggia.
Saturday is with Baby Machaca and Machaca-in-law. Good night for some casual but great chow in a place where we can eat early, relatively quickly, and with a baby. My wife's meeting is at the Chicago Hilton (720 S. Michigan) so something walkable from there would be great. (The other nights we should be able to get in the car, but nearer is a bonus.)
All suggestions very welcome (i.e. don't restrict yourself to the places I listed above, that's just what I gleaned from reading a lot on this board!)