Fricano's, boy does that bring back memories, all pleasant. Fricano's and Yan-a-se on State street were 'our' places when my wife and I dated.
For expertly grilled squid and/or octopus I would recommend, as did Bryan, Santorini. Santorini uses lump (pure wood) charcoal and their grilled items, including lamb chops, are very good.
Yan-a-se also had a charcoal grill and one of their weekly specials was grilled baby octopus, which was a favorite. Katsu, who was the head chef at Yan-ne-se, owns Katsu on Peterson, which is one of, if not the, best Japanese restaurants in Chicago. I'll link to a post by Mike G on Kastu, if anything Mike is restrained in his praise.
This was a great place for italian seafood dishes. It was a very romantic restaurant. However, I do remember two guys who were playing instruments and singing shaking me down for some bucks in front of my date. It was a first date and I was trying to impress this girl. Now it just seems funny. This place must have closed in the late 80s. Too bad.