I'm not everyone, but here are a few things I'm looking forward to. For the past few years I've used Pinkfest as my "down time" and I've very much preferred the low-key and relaxing things. Let me just do a core dump here ...
An evening in Oak Park. Din-din at Winberies, QST at Bar Louie and/or the Hideaway. (I assume Velvet Rope is toast, no pun intended.)
Steppenwolf has been mentioned. I've enjoyed our recent theater sessions, in particular last year to see Kinky Boots. (Yes, that one tune from that one Off-Off-Broadway musical we saw a few years back is still going through my head.)
I was thinking of an evening in the Boystown area starting with a happy hour at Trader Dan's, the bar that Ginger discovered, then dinner at a place such as Leona's across the street or Giordano's around the corner. Then do whatever there is to do in Boystown. I very much enjoyed the 3160 place last year.
I would to the Signature Lounge at the Hancock again, as long as I have a couple of adult beverages before I brave the trip.
I said I would be willing to coordinate a dinner at Harry Caray's Steak House, but there was already talk of going back to Lawry's, so I'll put that one on the back burner.
Redhead is "ok", and I'll go there if the gang wants to, but I think I would prefer Grape Street or 3160. The replacement for Gentry is "ok" as well.
These are just a few ideas ...