Spent a week in your lovely town and did a fair amount of good eating, both places I've enjoyed before (Hopleaf, Publican, Lou Malnati's, Intelligentsia) and new places for me (Blackbird, Naha, Al's, etc.).
First, a breakdown, then a bit more detail...
Highly recommended - The Publican, Weiner's Circle, Intelligentsia, Hop Leaf, Moto
Recommended - Blackbird, Frontera Fresco, Wow Bao, Al's Italian Beef, Lou Malnati's, Quartino, S&G Diner
Not bad - Naha, Mario's Italian Lemonade, Bin 36
Not so much - Water Tower food court
So, a bit more detail...
I hit Intelligentsia just about every day for a cortado or a valrhona mocha or just plain great coffee. The best Chicago dish of the trip was the char dog at Weiner's Circle. The coolest dish of the trip was the cuban cigar at Moto. The best bread of the trip? Publican. Best beer pairing of the trip? MOTO! in a surprise win over Hop Leaf and the Publican.
On the cheap end - in addition to a great chicago dog at Wieners Circle, I loved Wow Bao's coconut ginger chocolate bun, awesome snack. The savory buns at Wow Bao were good (thai curry, pork bbq), but the chocolate was flat out amazing. Frontera Fresco made for a nice taste of Rick Bayless' take on Mexican - had a taco and the tortilla soup, both very good. Malnati's is always a good Chicago deep dish. And an italian beef at Al's (dipped, w peppers) was good but not quite as great as expected (give me Mother's debris in NOLA or a good Philly cheesesteak instead, sorry Chicago).
On the high end - Moto delivered with tons of fun, creativity, and deliciousness. The cuban cigar? Crazy. The mexican cannoli with duck and mole? Love it. The chocolate bomb with marshmallow lit fuse? Awesome. I've eaten at WD-50 in New York, and Moto blows it away (based on one meal at each).
Blackbird had lots of hits and one or two misses, but was a really enjoyable meal with some really interesting flavor combinations.
Naha was up and down for lunch - why anyone would get their popular fried chicken salad there is beyond me - the chain Houston's (do they have that in Chicag?) does it much better - but we had a really nice duck confit with crispy duck skin.
All the pics I took at
http://www.flickr.com/photos/kaplanbr/s ... 188725033/ - both food and the city.
OH, and thanks for all the insights on this board, great stuff.