I feel like this should be called Foodie and the Feast...
The SO and I are coming up on our fifth anniversary (and technically our 11th together) in the second week of April, and we apparently miss Chicago Chef Week. For the occasion I would like to set up reservations somewhere nicer, though without a $200/person price tag. Anywhere in Chicagoland is a possibility for a good site, though we live in the western suburbs and he works downtown in the Loop. Therefore our striking distance is large.
Now here's the particular challenge: I am definitely something of a foodie with few opportunities thus far to be one, whereas my dearest SO is just as happy tucking into a hamburger and may not be quite so comfortable or impressed with a swirl of flavoured mousse. (My lifelong ambitions to get into Per Se or Masa no doubt will happen one day with a friend...) He enjoys most cuisines except heavily spiced (Thai, Vietnamese, Indian, and Chinese are not high on his list of preferences); fresh seafood and sushi, steak, Italian and American all go a long way.
I've read through many, many reviews and I'm overwhelmed by the diversity. Could we get a few nice recommendations for a lovely anniversary-worthy dining experience, and a good taste of some of Chicago's finer culinary talents?