So this Chicago trip this week is going to be split between there and Indianapolis, so it will be a quick one. Looks like we're staying at Sofitel Chicago Magnificent Mile off chestnut. What's good around there? @8manpick
Keeping within a few blocks of your hotel:
Regular Bars: Pippin's, Streeter's, Dublin Bar and Grill, Jake Melnick's or if you are willing to walk a half mile: local favorite Hopsmith.
Cocktail Bars: The Peninsula hotel's bar is my favorite fancy bar I've been to. RL Restaurant has a nice bar.
Steak: Maple and Ash, Tavern on Rush, Gibson's
Other higher-end food: Le Colonial (French-Viet), RL Restaurant, Francesca's on Chestnut
I can widen my recommendo's if you are willing to go further, just let me know what you're looking for.