Unlimited expense account for a week in Chicago
I agree. Topolobampo and Frontera Grill both, for regional Mexican cuisine, dishes you never see at most other Mexican places. A bit crowded and noisy, but great food. I prefer Topolobampo for the advance reservations, to avoid the angst of Frontera Grill, either risking waiting or trying for a same-day phone reservation.
Not sure if you want to stay downtown only. BUT if you want fantastic Ethiopian, Ras Dashen is amazing. The food is to die for! I will warn you, service is slow but it's because they want you to chill and relax so you do need to ask for your bill at the end. Also they have live music on Saturdays and some Fridays, really great!
Also, Toast (746 W Webster Ave) has a terrific brunch. Seating is better for 2 and the wait has never taken as long for us as they say it will.
We also LOVE M Henry (for brunch) in Andersonville. Long wait but SOOOOOOO worth it! http://www.mhenry.net/
Well, it really depends on what you're looking for. For example, you might want to go to our very best restaurants on a couple of nights, but seven nights in a row? You're more likely to want some variation, no? Maybe break it up with a pizza night or burgers, even if only for a change of pace?
You'll find links to discussions on various kinds of food around Chicago in this topic:
so that topic will help you get an idea of various kinds of food and where to look for recommendations.
In particular, you ask about the top chefs and restaurants in Chicago. There is a link to a topic discussing them, but here it is for your convenience:
That topic also mentions some of our more casual fine dining places.
If I understand your question, you're trying to go beyond the "where is the food good" question, and look at the "what makes this place different/unique" question. That's fine. Here's how I would answer that question for our top tables mentioned in that topic:
1. Alinea - food as theater and science, maximum creativity, the ultimate dining experience, high tech atmosphere, top bragging rights
2. Avenues - maximum creativity combined with great flavors and occasional whimsy, with the added luxury of the Peninsula
3. Everest - Alsatian flavors, the most exquisite service, great views from the top of the Chicago Stock Exchange building
4. Charlie Trotter's - maximum creativity and innovation
5. Tru - also maximum creativity (sorry to repeat myself, but these top places have a lot in common)
6. NoMi - ultra luxury, but a bit more relaxed, with a nice view of Michigan Avenue
7. Schwa - ultimate creativity, but very different in character, ultra casual and hip, goes beyond contemporary, more unstructured and unconventional
8. moto - again, very creative and unusual food, maybe the most cutting edge of all
9. Spiaggia - the only Italian restaurant in the same haute cuisine ballpark as the others
In the more casual arena...
one sixtyblue - incredible food, hip decor, more spacious than most
Aigre Doux - the newest place with all the buzz, the sticky toffee pudding
Blackbird - the most crowded of these places
Avec - the communal seating makes this a place where you make friends, whether you want to or not
Spring - casual elegance with an emphasis on seafood
Custom House - casual elegance with an emphasis on meat
Naha - a nice fusion of so many different food backgrounds
Sweets and Savories - the plain small storefront in the unlikely neighborhood makes it all the more surprising to find great food inside
North Pond - the elegant location in Lincoln Park is unique
I don't know if that's what you're looking for, but maybe that helps...?