So, the places I've been to, and my thoughts, in brief:
Alinea - deserves it all the way. One of the best meals I've ever had.
L2O - leaving aside the whole issue of the chef having just left, honestly, I was pretty underwhelmed by this place. We did the 12 course, I think, and as I recall, 4 courses were mindblowingly incredible, 4 were pretty good, and 4 were completely uninteresting. Maybe it got better in the interim, but now that the chef is gone, no way in hell am I spending the money to find out.
Blackbird: I've only been once, and I pretty much hated it. It was weird. I genuinely didn't like almost all of the food I got. But I think it might have been some kind of weird fluke. Part of me wants to give it another chance, the rest of me thinks that I can have a perfectly fantastic dinner at Avec for less money so why not do that?
Bonsoiree: Good, but I wouldn't say it was really star quality. But I did very much enjoy the meal I had there, and being BYOB helps a lot.
Longman and Eagle: I've written about their brunch before, and actually, looking back at my review I'm upset with myself for not updating it after return visits. Because their biscuits and gravy are seriously awesome. I've also gone for dinner, and the wild boar sloppy joe is pretty effin' incredible. I think it deserves its spot on the list.
Schwa: Any ranking that puts L20 over Schwa is pretty much bankrupt. Schwa is an incredible dining experience. Yes, it's a pain in the ass to make a reservation, but the food is out of this world. Except for the one fish course with cotton candy that seems to be on the menu in some form every time I've gone, that I didn't really love, despite trying to every time. But everything else is seriously amazing. The fact that it's BYOB, the unbelievably attentive service - how often does the chef come out to tell you about your meal? For every gdamn course? Honestly, I loved Alinea, but Schwa is hands down the best dining experience in Chicago.
Sepia: I'm stoked to see Sepia make the cut. I've only had lunch there, but it was phenomenal. I'm looking forward to doing dinner. But I'm biased, because I'm in love with one of the servers.
Takashi: I've written about in detail already. What it does right, it does superbly, but there's also a lot that's kind of forgettable. I actually do forget about the place - it pretty much never comes to my mind when someone asks me for recommendations for amazing meals.
Ok, less detail for the Bib Gourmand, because I grow weary of this process, heh heh.
The Bristol, Gilt Bar, Lula, mado (though they just got a new chef), Urban Belly - yes, most definitely.
Girl and the Goat probably deserved a star. Also, I'm skeptical of the idea that you can do it for under $40. The Publican also should've gotten a star
The Purple Pig, yeah, probably deserves its spot.
Nightwood I've only done for brunch, but it's frickin' awesome.
The Paramount Room - really? I mean, I love the poutine, and the cocktails are great, but... let's not go overboard. Not least because it's a tiny menu. Hopleaf also - I mean, they do have an amazing beer selection, and the food is good, but it's not exactly an extensive menu. If you're going that route, why not the Skylark? Or In Fine Spirits?
Veerasway - I LOVE the cocktails. They might even be my favorite in town. The food is completely unexciting and is wildly overpriced. I'm slightly offended to see it on the list, especially with not a single place on Devon making an appearance.
Han 202 - also irks me, especially given that Lao Beijing and Lao Szechuan aren't mentioned, and both are probably some of the best Chinese food you'll ever have in your life. Han 202 is fine as far as $20 5 course dinners go. I don't know of any other place where you can get a 5 course dinner for $20. But personally, I'd rather spend the $20 on fewer courses of higher quality somewhere else.
Nana (yes, I realize these are in no particular order) - I've had brunch there, it's pretty good. I definitely wanna try the dinner.
I'm surprised that Kuma's and Hout Doug's didn't make the cut (though the lines at Kuma's annoy the hell out of me). Personally, I think Province, Gioco, and maybe Deleece deserved a spot on the Bib Gourmand for sure. I'm downright angry that Lao Beijing isn't mentioned. I think Sticky Rice deserves a spot, but I acknowledge that it's not so well known. Overall, ethnic restaurants should've gotten more attention, but it's not surprising that they didn't get it.
Overall overall - meh. I'm unimpressed.