What about Fischman's - like an old-man bar with fancy drinks & both fancy & non-fancy clientele.
4780 North Milwaukee Avenue
Chicago, IL 60630
(773) 545-0123
The Windsor tavern is closer to the Portage (I'm guessing theater, not restaurant you mean), seems to fit the bill, but i've never been there.
If you mean Portage restaurant, i'd go to Bim Bom, a friendly lo-key mostly Polish clientele place with foosball sharps and a Gehry facade.
5226 W Belmont Ave
(between Laramie Ave & Lockwood Ave)
Chicago, IL 60641
(773) 777-2120
paul