Anniversary Weekend in Chicago
 

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.

After dinner, maybe a carriage ride along navy pier or something? Or maybe a comedy show?

Any suggestions - regarding the hotel, restaurant or activity after dinner?

Thanks :)

Depending on your budget, food tastes and how romantic of a restaurant you're looking for, I'd consider dinner at:
Graham Elliot
L2O
North Pond
Naha
Topolombampo
Bin 36

What month & day of the week will you be in the city?

On Wednesday and Saturday nights you can catch free fireworks off of Navy Pier (but visible from many locations downtown).

You still have at least a few more weeks for free concerts at Millennium Park.

A lot of the rooftop bars (which are often connected to hotels) offer a great view and nice way to unwind after dinner.

Thanks. Those restaurants are interesting!

Its actually next weekend, the 3rd & 4th.

Oysters, champagne and Sybaris.

http://www.sybaris.com/modules/locat...oom_Group_ID=1

Great idea, you will enjoy the Penninsula. You might consider dinner out at MK Chicago or Kiki's Bistro if you want something more local. You could also have the Penninsula's chocholate buffet on Saturday.

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.

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.

Zanies or Second City are generally pretty decent for comedy. As an alternative, what about some genuine Chicago Blues at Rosa's?

I would definitely pick Rosebud Steakhouse, especially over Capital Grille. Great food, service and location.

How old are you and what's your personal style?

The Peninsula is traditional and old school (witness the high tea and marble in the lobby). If that's your style, you'll love it. The Park Hyatt across the street is more contemporary with a younger vibe (and probably clientele).

Thanks all for the suggestions so far! The date is getting close, so I better figure it out soon. With all of your help, I have a ton of restaurants to choose from! I'll scratch off Capital Grille.

Yahtzee - Early 30's. I just checked out the Park and it does look nice! However I don't think they have any availability acording to the website. I might be able to call amex and see if I can get a room or not.

I am set on the chocolate bar at the Pen though!!:D

The thrill is gone??

Haha:D

Not at all, we'll have lots of calorie burning activities after the chocolate bar;)

Food and service were excellent at David Burke's. Steaks were fantastic.

Thanks. I think I've narrowed it down to Graham Elliot or David Burke's and maybe Keefer's.

Thanks. I've been to Zanies in St Charles and to Second City in Chicago and saw the 50 Years of Funny show. Where do you think is better in Chicago - second city or zanies? I'm thinking a comedy show instead of the carriage ride, but not sure.

Thanks, we've stayed at the Sybaris several times, in fact 2 anniversaries ago. I'd like to take her downtown this time!

Do David Burke's for food and service. Atmosphere is steakhouse, nothing fancy.