I have a good friend coming in town from New York to celebrate his birthday here in Chicago for the second year in a row, and he will be staying at Hotel Monaco (Wacker and Wabash). He had an amazing time last year. I took him for drinks at The Signature Room for the view, missed our reservation at Aigre Doux because we were enjoying the view so much, then we went to a comedy show and The Drawing Room for late night drinks/food. Saturday we did Cafe Spiaggia for lunch and Mercat a la Planxa for dinner (kind of underwhelming, although still a good time). I'd like this year to be just as good, but I'm kind of driving myself nuts figuring this out.
He wants something low-key, so I was just planning on having an indoor picnic of gourmet sandwiches and mac n' cheese and wine because it is so terrible out and I thought it would make for a cozy night in. Although any cozy bar suggestions are welcome.
He works during the day, so blackbird or Naha's lunch is out. I was thinking The Publican or Kith and Kin for dinner. Something fun and comforting but still delicious.
My biggest problem is with Saturday lunch. LOVED last year's lunch at Cafe Spaggia because we spent hours over a couple bottles of wine and wonderful food. Would like to recreate that upscale intimate lunch (not brunch) elsewhere, but cannot find anything.
Dinner I was thinking North Pond for the view, but I've heard really mixed reviews about service, portion sizing, and a lot of other such issues. Perennial is a potential. Any other ideas?
If I don't do dinner at the Publican, brunch here is an option. Still trying to figure this one out, but there are a ton of great choices, so this one is up in the air too.
I know this is a ton of information I threw out there, but feeling a bit lost. Thanks for any and all help!