Three nights in Chicago
We are coming to Chicago in mid-March and looking for three must-do places to eat. Last summer we ate at Alinea and Frontera Grill. I am most tempted to go back to Alinea for the 24 course (only did the 12 course last time) but am interested to hear what CHs would rate as their top three.
Well, I'd certainly suggest a return trip to Alinea, especially since they change the menu frequently. Along the same lines as Alinea are Avenues and Moto. Both are excellent -- Moto tends to be the most creative/scientific of the three, but all focus on high end dining with much creativity. Also, keep an eye out for the reopening of Schwa . . . similar in creativity and quality to the above three, but pretty casual (nice jeans would be acceptable) and byo, making the $95 tasting menu quite the deal. Rumors have it reopening within a month or so, but who knows. All of the above four are outstanding.
Now, in terms of "top three," I guess it depends upon how much fine dining you want. Do you want the best splurges, or the best food in their categories, including cheap eats? Other top fine dining destinations would certainly include Spiaggia, Everest and Charlie Trotters. There's also NoMi, Tru and Les Nomades, but I like the preceding three more (although I have not dined at Les Nomades in a long time). And if you liked Frontera, I suspect you'd also like Topolobampo (Frontera's upscale sibling). One place that really flies under the radar is Sweets & Savories, where they do a fantastic tasting menu (more traditional than Schwa or any of the ultra-creative spots), but in a more casual setting than the above mentioned more formal spots.
Blackbird has always been my favorite of the 2nd tier-expensive restaurants. That is, it's not at the same price point as an Alinea or a Trotters, but the food is fantastic. In that same category, I also would recommend North Pond. I prefer Blackbird, but North Pond has one of the most beautiful locations in the city and the food is excellent. And Naha and One Sixtyblue are also excellent in this group.
And then if you'd like less expensive gems in Chicago, I'd suggest Spoon Thai or TAC Quick for amazing Thai food (search the Chicago page for the Translated Thai language menus for the best menu items). Chicago also has a number of outstanding Mexican food, including Frontera and Topolobampo, but my favorite is Sol de Mexico.