I live in Chicago & frequent all of the restaurants, save the two which only recently (re)opened... B&B Bagels on Touhy and Shallots Bistro (though I have been to Shallots before they moved- worked there, too).
Bugsy's ribs, BTW, used to be a different cut. They changed it about 6 months (?) ago. Personally, I like the old cut better, but at least they're charging double for the new one! And yes, their Tollhouse pie is well-renowned in Chicago. If you want to be sure they'll still have a piece for you when you get there, request it when making your reservation- really!
Favorite milchig place: Slice of Life (which is the 'other side' of Hy Life Bistro). They have amazing soups, pretty good pizza, and amazing pastas. They also have a full-service bar, which yes, is very rare in Chicago restaurants. I don't know of any other place (save Shallots) where you can order any alcohol whatsoever. Really.
Favorite fleishig place: Taboun Grill. By far. Their Yemenite soup is amazing- and the shwarama is always fresh. They also have the best pita and best schug (harif, hot sauce) in Chicago. Real authentic place- but you'll pay for it on the scale later. They're pretty heavy on the oil.
Best grab-a-bite-and-go places: fleish: Ken's Diner, the 'other side' of Bugsy's. Get the Bay-Ken burger w/ paerve cheese. Fool all your coworkers! milchig: Tel Aviv, next door to Taboun but under different management/ownership. My husband swears by their whitefish dinner- I love their veggie lite (essentially a cheese-and-bean burrito). Reliable quality, real low prices (2 people can stuff themselves for $20), and friendly staff (it's counter-style, no servers).
Got more questions? Post it, I'll tell you all about it... Glad to see there's conversation about us in Galut outside NY ;)