Anniversary Weekend Food Extravaganza

My husband and I will be staying downtown (Kinzie and State) to celebrate our first anniversary in October (yes, I am planning very far in advance). We have tickets to see Wicked on Saturday afternoon, but we want to spend the rest of the weekend eating ourselves into a stupor.

I've culled a list of possibilities from this thread, but I'm having trouble narrowing things down.

The plan is this: dinner Friday night (I'm thinking Topolobampo), breakfast Saturday morning (Orange, perhaps?), late lunch after Wicked (dim sum or thai, I'll research the recommendations made in the thread I linked to above), dinner (TBD), Maxwell Street for breakfast/lunch on Sunday before heading back to Oak Park.

I'm completely open to suggestions for all meals, but I need the most help for Saturday's dinner. I'm looking for some truly top-notch food, but I'm not looking to spend a small fortune on one meal (eliminating Charlie Trotter and Tru, I'm guessing) and while I'd love food that has some flair, I don't think I'm up for a place that's attempting to reinvent dining as we know it (eliminating Alinea and Moto, I'm guessing). I don't think Avenues will be a good fit since I'm not a big seafood eater (although my husand and I are giving sushi a try this weekend, so perhaps that will change).

Also, since we'll be consuming a good amount of Asian and Mexican food during other meals, I'd like to try something different for Saturday night (but I'm open to fusion-type places -- Opera, maybe?). I'd love to try an indulgent, upscale Italian place, if one exists. We won't have a car with us, so CTA accessibility is essential.

Any suggestions for Saturday? Anyone want to steer me away from some of the places I'm leaning toward?

Since Chef Bowles took over, Avenues is no longer specifically a seafood restaurant. It is a little on the expensive side, but less so then Tru or Trotter - I think it could be a good option to consider. You can download menus on the Peninsula's website.

AlissaS24 wrote:Also, since we'll be consuming a good amount of Asian and Mexican food during other meals, I'd like to try something different for Saturday night (but I'm open to fusion-type places -- Opera, maybe?). I'd love to try an indulgent, upscale Italian place, if one exists. We won't have a car with us, so CTA accessibility is essential.

Any suggestions for Saturday? Anyone want to steer me away from some of the places I'm leaning toward?

How about Spiaggia? That's an indulgent, upscale Italian place or even Cafe Spiaggia if you're budget conscious. Also, If it were my choice for breakfast, I would choose Lou Mitchell's over Orange any day of the week. The food is much more straight ahead Greek diner food, but the atmosphere and sense of Chicago history can't be beat.