Ok, so I took a peek around the last few pages... some thoughts.
Pizza = Uno or Due on Grand. Yes, it's in the loop. If not there, Lincoln Park has Lou Malnati's, and there's a Giordano's EVERYWHERE.
Millennium Park...?
Belmont/Clark neighborhood. Trendy, but as long as it has The Alley there's uber cool shit to look at and gawk.
Lakeview: see above
Pubs/nightlife: All over. I would suggest staying out of Lincoln Park on a weekend but the Lawrence red line stop has this place I go to called the Fat Kat Lounge which is pretty sweet. Green Mill's usually hard as shit to get into, but a Sunday Night poetry slam might be worth it...?
The riverwalk is now open!
August, I'm sure there'll be a street/neighborhood festival around then.
As far as in the Loop goes, Millennium Park stuff/Navy Pier/Beach volleyball/zoo/random parks/trails all apply.
Oh hell. Almost forgot, Whirlyball (bumper car lacrosse, basically)!