What are the best not super expensive restaurants in Chicago?
Check out the Michelin Guide. They rank the best restaurants with one to three stars and most of these are of course expensive, but they also have a separate 'Bib Gourmand' category.
Bib Gourmand restaurants "indicate quality restaurants that are affordable (less than $40 for two courses plus dessert)."
There are 64 BG restaurants in the 2013 guide. You can browse the list here:
http://articles.chicagotribune.com/20... ... I don't even live in Chicago but a lot of those names are familiar to me from Chowhound :)
My favorites would be Embeya (Asian Fusion), the Lobby (Contemporary American), Boka (Contemporary American) and iNG (Modernist Cuisine). None of these is cheap by any means, but I have had consistently great food and service at these venues and they are significantly cheaper than Chicago's priciest restaurants. You can have a nice dinner and moderate alcohol for $100 per/person (before tax and gratuity) at all of these (Embeya even less than $100).
To Gonzo's list, I would add Perennial Virant as a nice spot that is within your price range.
As to restaurants well below that price point -- in the spirit of a "dive that's awesome" -- you might consider Sun Wah, where you will be hard-pressed to spend $30/pp. It' s a Chinese restaurant located in Chicago's Uptown neighborhood. Reserve at least one day in advance and preorder the Peking Duck.
Chicago has tons of options in the $80 -100 price range. In fact, if you're not having a lot of alcohol, you can go to Naha for example in that price range and they are among the very best.
Inovasi in the suburbs is less - and worth a train ride as is Paul Virant's Vie.
We recently had a lovely meal at Vincent - some truly stunning dishes and good cocktails.
I'd second Sun Wah as well.
(I would not, btw, trust the Michelin ratings for Chicago which many of us feel miss the mark in terms of selections).