Sorry for bringing up ol' #6 (the Padres had his number placed on the outfield wall where he hit that homer; although it is no longer there since the move to Petco).
Getting back to the OP (me):
New Itinerary:
Friday:
Breakfast - at Orange (or Dunkin Donuts if my fiance gets her way!)
Lunch: Al's #1 (with a Lemon Ice from Mario's)
Dinner: Boka
(Second City)
Drinks - Signature Room (or Matchbox)
Saturday:
Breakfast: Lou Mitchell's or Uncommon Grounds
Lunch: Hot Doug's or Weiner's Circle
Cubs v. Padre game at Wrigley
Dinner: Custom House (should I do this or Gibson's?)
Late Night Snack: Lou Malnati's Pizzeria
One last point. My fiance is Greek, so, we may need to sub out the Custom House with something in Greek Town....any ideas?