Chicago is the center of the librarian webiverse.
Sites by or for librarians, from folks in Chicago or the 'burbs:
Bookslut (not specifically for librarians, but a must-read)
'Brary Web Diva
Convivial Librarian
The Crafty Librarian
The Curmudgeony Librarian
debgpi
The Laughing Librarian (plus librarism.com, of course)
Library Underground (including the Chicago chapter)
LISjobs.com
Sarah Ann Long
Lyonette Louis-Jacques
Morton Grove Public Library (registered "Webrary" as a trademark!)
Ref Grunt
ricklibrarian
Rockhack
The Shifted Librarian
Daniel D. Stuhlman
That Rabbit Girl
thatbob
Walking Paper
Terren Ilana Wein
wrybrarian
Young Librarian
A few association HQs: ALA (including PLA and other divisions), AALL, MLA.
Not really in the Chicago area, but not too far away:
Marylaine Block
Tales of the Slytherin Librarian
Tinfoil + Raccoon
And let's not forget:
Every Library in Illinois