Originally Posted by gallardo
I'm thinking of staying at the Peninsula Hotel and maybe going to a nice restaurant, maybe David Burke's or Capital Grille? We go to Ruths Chris pretty often just as a nice night out and just went to Gibsons a couple weeks ago, so would like to try some place new.
If you like steak, (& it sounds like you do) then both David Burke & Capital Grille are good options, though I'd give the edge to David Burke (they offer dry aged beef rather than wet). Another option to consider is Keefer's, which has a bit more eclectic options in addition to steak & a slightly more casual, hip atmosphere.
After dinner, maybe a carriage ride along navy pier or something? Or maybe a comedy show?
The carriage rides don't go down the pier IIRC, but they will certainly take you around the Michigan Ave area. If you like cocktails, a good place to try nearby is The Redhead, which also has a live piano player & singer doing jazz & club standards. Also, if you like chocolate, the Penninsula has a fab chocolate bar in the Lobby Fri & Sat nights, & they often have a live jazz trio.