taking my parents out for their 40th anniversary
I'm going to be in Chicago next weekend, and my sister and I would like to take our parents out for their 40th anniversary. We want to take them somewhere special and memorable, but their style is pretty casual and off-beat - they're happier in a funky deli than a swanky white-tablecloth dining room. Their palates are pretty traditional: American and European is good. They love "discovering" places with local flavor.
There is a solid and somewhat casual steak place on the north side called Cordis Bros. Supper Club (on Irving Park west of Ashland; take a cab from downtown, a half-mile west of Wrigley Field). The steaks are very good, and the atmosphere is intentionally retro. Food overall is very mainstream. Reasonable wine list. It is not like the crowded and expensive steak houses downtown.
It's hard to reconcile "somewhere special and memorable", on the one hand, with "pretty casual and off-beat" / "funky deli", on the other.
If I were to recommend a place for a 40th anniversary, it would have to be a "white tablecloth" kind of place - not necessarily super fancy or super expensive, but at least in the "casual fine dining" category, rather than a place that doesn't have that "special" vibe. Given what you have stated, I would suggest a nice place but with a bit of a laid-back flavor, somewhat off the beaten path - either Sweets and Savories at the west end of Lincoln Park, or Lula off Logan Square.