Dinner in Old Town (before Second City)
I am going to be in Chicago in three weeks for a little R&R. We are seeing Second City (I believe this is in Old Town) and would like some recommendations for some Chow. We don't want to get dressed to the nines, but are willing to spend money if the place it right.
Another vote for Bistrot Margot. They feature daily risotto specials that are frequently excellent. And my favorite steak frites in the city. More casual than Salpicon, which is another excellent choice. Salpicon is one of the few restaurants in that price range (pricey but not "jacket-required" pricey) with proper wine service.
Adobe Grill is a good place for drinks, but the food is average. Within walking distance I would recommend Salpicon (Zagat 24 - upscale Mexican). I ate here last Sunday and had a terrific experience. Other options include Dinotto (Italian on North), or Topo Gigo (lively atmosphere and good food), which are both casual.
Someone will probably recommend Adobe Grill, which is in the same building as Second City, but I've never found the place to be more than convenient. A short drive away from Second City is Grand Ave. west of the Kennedy Expressway. It's an old Sicilian neighborhood. I like Bella Notte for Italian there. May Street Cafe (I think that's the name) is more innovative and has gotten good press here and on LTHforum.com. MSC is just past Bari Foods, a prized little grocery, and D'Amato's, arguably Chicago's premier Italian bread bakery.
I think you mean May Street Market at the corner of May and Grand. I love MSM, but there are a lot of good options within walking distance of Second City.
Second City is at the corner of North and Wells. If you start at North Avenue and walk south, you will pass by at least a dozen restaurants - many mentioned below. Its a nice walk through a busy neighborhood.
If you like to cook, I would definitely plan to stop by The Spice Store about half a block south of North. Just about the best selection of spices you will find everywhere. Even for the beginner cook there are lots of excellent spice mixes and rubs.
My chow favorties - Salpicon and Topo Gigio, both mentioned by other posters Salpicon is the best and most unique (and costly) of your options, but depending on your preferences, there are a lot of other choices:
Dinotto - Italian across the street from second city.
Trattoria Roma - Another Italian
Kamehachi - OK Sushi.
Bistro Margot - Good French Bistro - used to be one of my favorites, although my last visit was not up to the previous standards.
Fireplace Inn - Ribs
O'Briens - Irish pub with lots of slightly upscale American Bar food options.
Old Jerusalem - very causal but good middle eastern - BYO
And of course Las Pinatas - great place if you're in your early 20s and crave Quesadillas, Nachos, and some of the strongest margaritas this side of the Rio Grande.
Mizu Yakitori and Sushi Lounge is very close to Second City and would be another option if you are interested in Japanese. It is located in the 300 block of North Ave. Angelo's Taverna (serves small plates/tapas) and Twin Anchors (Good ribs, classic Chicago bar) are both on Sedgewick just a few blocks west of the theater.