In no particular order:
~1~The Maxwell Street Polish sausages at the Old Maxwell Street market, pre-the 1994 move. They just don't taste the same as they did on Maxwell Street. For serious.
Heck, I miss the entire Maxwell Street Market shebang. What an....experience. No other way to describe it, really.
It used to be located across from the Steppenwolf theater (now it's some froufrou wine bar or something). The Steppenwolf actually salvaged the beautiful bar and they use it as a set prop at times. I actually got to see it in The Time of Your Life.
It was always quiet and dark inside O'Rourke's, even on a crazy summer Saturday night, with dim lights and gleaming dark wood; and the bartender served the best pint in the city.
Como Inn. It was and still is my favorite restaurant EVER in Chicago. Sometimes my friend Jess and I would get totally gussied up and go there for dinner. Just 'cuz. When I was a kid we'd go there for the most specialist of special occasions.
I still miss seeing it from the expressway (when I actually do drive into the city and get off at Ohio).
The Family House restaurant where I first got drunk on Ouzo. Actually, it was the only time I got drunk on Ouzo. I was, like, 7 or 8. My dad kept ordering Ouzo then he'd get up to go to the buffet. I loved the smell of it (black licorice!), so I drank it. YUM! My dad would ask the waiter about his ouzo as "his" empty glass was "still" sitting there, so they'd bring him a new one. Which I prompty drank as he went to fill his plate again. The third time he caught me but was too stunned (and maybe a little shock-proud in a dad sorta way) to stop me. I remember being really tired shortly after not-quite-finishing the third snifterful, and I remember being forced to walk around the block with Dad a few times when we got home, even though it was really cold outside.
They served. The BEST. Greek food. EVER.
Still can't drink Ouzo, though I do LOVE black licorice.
The Family House has been closed so long it doesn't even show up in a Google search. I'm sure it wouda had it been closed for serving to 7-year-olds.