If you visit any of the above good recomendations, you should be able to save money, earn miles or both.
Goose Island and Angelina's certificates are on restaurant,com and El Jardin and Byrons are part of Rewards Network. I believe Yoshi's offers something also.
If you are looking for a hole-in-the-wall unique to Chicago, visit Al's Italian Beef.
Lastly, Luck's gets alot of hype because it was featured on "Man vs Food", but this place is far from my favorite.