Just went last week. I managed to hit several places that I've never been to before including:
M Burger - I thought that the burger was pretty good (gotta get the M Burger), the fries were so-so, but I didn't try the malt as I am a cheapskate and thought that $4 was too expensive. The nice thing is that it was right across the street from my hotel.
Heaven on Seven - Went to the original location with a friend who has lived in Chi-town longer than I did and he'd never been there either. We both had a cup of the gumbo. He went with the soft-shell crab po' boy and I had the jambalaya. He won.
Twisted Spoke - Went here to meet friends for burgers and beer. Pretty good beer selection, prices for beer weren't bad. Burger was pretty mediocre. I wouldn't get it again.
MK - Saved the best for last. I've wanted to go here for years and my friends who I was meeting up with happened to picked it as one of two places for me to choose from. It was incredible. It might be worth going there for desert all by itself. If you find yourself going, the grilled octopus app was probably the best thing we had all night.
Teuscher - Had to stop in here to pick up some sweets for my sweetie. Damn is that expensive, but well worth it. Also, stopping here gives you and excuse to stop in and see if there is anything nice at
Mark Shale Garrett Popcorn - I know it's a cliche, but I'm a sucker for cheese corn.
Corner Bakery - Yes, it's on virtually every corner that Walgreen's isn't, but I love that oatmeal with the cinnamon raisin toast for breakfast. Found the perfect red dress socks while at Paul Stuart. I've been looking for those for like a year. Edit: How could I forget, I also made a stop at
Jazz Record Mart. I don't know much about jazz, but the helpful folks there took what I knew and introduced me to Grant Green. Idle Moments is becoming one of my favorite albums.