Hello, I'm planning my sister's surprise 30th birthday trip. She's flying in from LA (doesn't know it yet), I'm flying in from Boston, and other friends coming in as well. We chose Chicago because it's a great city she hasn't visited before and because she absolutely loved MY 30th last year, so we wanted to do something similar but not, obviously, exactly the same, for her. For my birthday, if you are familiar with NY, we did dinner Friday night at Butter, Saturday sightseeing, Saturday (birthday) night as Asia de Cuba (my sister loved it), saw a show, went dancing, then Sunday brunch at Asiate in the Mandarin. We all stayed at the W. For my sis, we're also staying at the W, and I'm looking for the following:

A young, fun, hip/different/interesting (not SUPER pricey) place for dinner Friday night (maybe something cool with an entertainment factor to it);

A very special, fun, hip (pricey okay) good food restaurant for Saturday night (her bday)-- think similar to Butter or Asia de Cuba style in NY (two that I seem to have noticed on the internet are N9ne and Blackbird--thoughts?);

and

Possibly a great brunch place for Sunday (someone suggested a restaurant that is very high and rotates-- in Oprah's building).

Finally, they should all be relatively centralized. I'm planning this part of the trip, but I've never been to Chicago! Thanks.

Our favorite restaurant in Chicago: http://www.alinea-restaurant.com/ Absolutely amazing in every way!

I arranged a dinner for Italian and German reporters at N9ne (with cocktails at Ghost Bar). They really enjoyed it, great atmosphere, good marks for the food and service. The only catch was that it was rather noisy when in full swing (I felt the same way about Bin 36--it should be called Din 36). But for a celebratory, social evening with 20- and 30-somethings, it's a smart choice.

For Sunday brunch, there are many possiblities. The Sofitel Water Tower Place restaurant has a very modern French vibe and I *loved* their macadamia nut pancakes. If you linger there past 3 pm, their bar is also a hopping place with more than just hotel guests.

You didn't say when exactly you were making this trip. Because if you do have aspirations of dining at Alinea you'll need at least a months headstart with reservations. There is no comparable restaurant in this country.

I just LOVE Bistro 110's Sunday Jazz Brunch. Live music, fun atmosphere, delicious food. Best yet, you can make your reservation on www.opentable.com

http://www.levyrestaurants.com/Levy/...Bistro+110.htm

These are great comments. The Alinea place looks a little too stuffy for what I had in mind. More young/yuppie/hip/fun/scene w/ good food than "star, 7 course meal" is what I had in mind. That brunch place sounds like something I will definitely check out. Would love to get more thoughts on N9ne, as well as Blackbird and Japonais. If my sis isn't a sushi girl, will she like Japonais? They seem to have a variety, but not sure if its one of those, get sushi or it's not worth it places.

p.s.--Mid-Cotober

Yikes. Sorry to post again-- that should be mid-October. Also, is N9ne meat-marketish? It kind of looks like it in the pictures. Between Blackbird, N9ne and Japonais, what would you pick? Japonais seems right now like it might be the best compromise of "scene," fun, and good food for an LA girl. Thoughts?

Well, I don't know, Nine seemed like kind of a sleek Euro-feeling, but basically steakhouse to me. For example, we saw Johnny Damon there last year. Blackbird is trendier in feel to me. Might also consider Le Lan or Kevin's.

For Friday,what about Pops for Champagne, a long-time Chicago favorite that recently moved from Lakeview to North State Street. Live music, lots of champagne, dinner, desserts, etc.--intimate, romantic.

I second Bistro 110 for brunch. Yummy. If price is no object, I'd recommend Tru for dinner. It was like Cirque de Soleil (spelling?) with food. Really worth the money.

Don't have a suggestion for dinner... the restaurant's mentioned are all great...but for entertainment you can't beat Howl at the Moon. It's a dueling piano bar on Hubbard Street,right in the center of town. They'll have your sister get up on the piano while they sing to her..It's a blast!

Alinea is far from stuffy. However, it is a destination restaurant - where you go to experience the most exquisite food you've had in your life. It's at least a five hour night and it's all about the experience. If that's not what you had in mind, then I wouldn't recommend it.

I just thought of a couple of places that would be lots of fun with great food - Spring http://www.springrestaurant.net/ and Roy's http://www.roysrestaurant.com/

FWIW, Alinea has just been named the best restaurant in the country by Gourmet Magazine.

That's great news, DRJ! I'll tell you - it deserves it. Have you ever dined there? Just amazing in every way.

By the way, if you do the brunch at Bistro 110, make your reservations after noon, cause you can't drink till then. They make a killer Bloody Mary ;-)

Somehow Alinea doesn't sound at all like what lukesaunt is looking for -- but I'm enticed.
So the big question -- what does this experience cost? Do I have to sell my house or just take out a second mortgage?

Nevermind. I found it on the website after all (tiny print below the lists of items in the two menus). $125 for the tasting menu or $175 for the "tour" menu. Less than I expected.

Neo - I went for a girls' weekend this past summer. We spent around $465.00 p/p, with tax and tip. It included their top tier wines, paired, and 25-27 courses, can't remember....

Hmmm. So if you did the "tour" at $175 each, the wine was another $580 for the two of you (less the tip and tax, that is)?
Or just under $1000 for the two of you?