Now that I humiliated myself on the Europe board, lol:

I've searched, I've googled. I've read reviews. This is our yearly "take the clients to dinner" trip. 2 nights, 2 different places. My hubby's pres of the company, so I get the job. Last year it was Aria (loved it) and Trattoria #10. (good, not great) So, we need a place with entrees in the not over $35 range ideally. That rules out Tru, Alinea and Spiaggia. Also, don't like really stuffy atmosphere as we tend to drink a bit.I was considering Topolobampo on Friday, but they only have a 6:15 and that is too early. Someone suggested Tuscany, but that looks a little TOO casual. ? Okay, I'm open for suggestions!

And, unfortunately, you haven't said whether or not type of cuisine is at all important.

have another cup...don't spill it this time LOL.

Does it HAVE to be Italian?

A very nice restaurant downtown in that price range is Roys, a pacific rim fusion place. The entreeP are creative and themenu is different in some way every day. The chocolate souffle is fantastic as in the bread pudding.
Carmines and Rosebuds are good choices for Italian food though are casual. I am not sure what you mean by too casual however.
Lawrys for prime rib is a Chicago landmark.
What about steaks? Eli's, Ruths Chris, Mortons, the Chop House, Charlie Trotters and Gene and Georgettis are a few that come to mind.

Recommend BOKA on N. Halsted.

Are you doing anything afterwards? Theatre, etc.? BOKA is very close to The Steppenwolf and Royal George Theatres. And Landmark is just down the street.

Linda,
Check out n9ne (Nine). It's a very contemporary setting. Good food, great atmosphere.

Good luck.

Okay, second cup. Just got flamed by some pompous type named pinch mewho said "wow" your hubby's pres and you don't want to spend blah blah...
Here's the case....we entertain clirents in all sorts of ways. My husband took 2 to Scotland for a week of golf at the championsghip courses. But sometimes, you entertain people who aren't upper level management and would feel a bit happier in a less stuffy, 5 star environment! (We also treated 2 couples to the Wine Spectator event) Some of these pretentious places fawn all over you and frown if you get the giggles after a few drinks, etc. So, there's always a nice medium in restaurants where you get great food in a nice atmosphere that's not over the top! As far as cuisine, they are both couples in 40's...I don't think sushi restaurants are a good choice unless you know their tastes. I prefer eclectic...variety. Aria was a great choice last year, btw.

Oops...no we're not doing anything afterwards except throwing back a few at the hotel bar, lol. By "too casual" I mean families, Maggiano's , etc. Anyone try Vivere?

Jacketwatch: Charlie Trotter's is like 100+ a plate, isn't it?

I can recommend Roy's, though I disliked the service there. The food is delicious.

I'm going to have my husband call them and make sure they like seafood, cause Roy's looks amazing. Love those kind of flavors. Also looked at Nine...but was put off by the "smoking area". I don't patronize restaurants which allow smoking. Too many others that don't allow it.

We were in Chicago a few weeks ago and enjoyed Tamarind - an Asian fusion restaurant one block behind the Chicago Hilton (the one on Michigan Avenue). In fact, we went there twice we enjoyed it so much.

I always love Blackbird or Avec. A new one is Table Fifty-Two (www.tablefifty-two.com). For steaks, try Custom House (www.customhouse.cc)--haven't been there myself, but love the chef's other two restaurants in the city, Spring and Green Zebra, and it gets consistently good reviews, so I'm pretty comfortable recommending it.

Enjoy!

I think you will really like Roys. It started in Hawaii and we first tried it on the BI. I do think there it was a bit better but of course the fish are as fresh as can be too. Cheers, Larry