I'm so out of practice with late dining, I realized last night that most of my handy picks for this situation are gone. Iggy's used to be our go-to spot, but both have closed. A good strategy is to head for an upscale, bar-dense area: plenty of drunks with money to feed at 2:00 a.m., and there's always valet parking. We ended up at the Bar Louie on Randolph. Which was fine. But it's definitely time to tune-up my list of possibilities for late Friday and Saturday nights:
Avec: Christ, I feel like whenever a restaurant question in Chicago comes up, the answer is Avec. Great food on Randolph in the near West Loop, killer wine options, open til 1:00 a.m. My only complaint is that it's a head-rattling little noise box when it's super busy, which is most of the time. However, we happen to have a monthly spot in the parking lot directly behind it, so...free parking trumps noise.
The Bluebird: This yummy gastropub on Damen in Bucktown serves its full menu until 1:00 a.m. I need to return to explore it more, but the theme is rustic, fresh Mediterranean, heavy on the Spanish and Italian, with great wine and beer pairings.
Paramount Room: This place is a hidden gem on Milwaukee in that weird zone of the West Loop where Iggy's used to be. I never hear much about it, but my wine friends like to go. The upstairs is just a tiny little dark bar - so tiny that everyone sitting inside turns to look when you open the front door. Head downstairs for a slightly larger dining area with wonderful French pub food and a great wine list. Open until 2:00 a.m.
Jerry's Sandwiches: Their deli on Division in Wicker Park serves 100+ sandwiches and craft beers until 2:00 a.m. I haven't been yet, but my downstairs neighbor Dan gets glassy-eyed just talking about the place. It's worth a go.