Chicago with Girlfriends
I'm going to be spending 2 nights in Chicago w/two good girlfriends in late October. I'm looking for a couple of good restaurants with great food where, hopefully, we can hear each other talk and have a long, leisurely dinner without being rushed. Sushi is out as one of the women is pregnant, but otherwise no limitations. We'll be staying near the Magnificent Mile, but don't mind travelling to another area of the city.
You said, "Sushi is out as one of the women is pregnant" - but why can't you go to a Japanese place that has both sushi and cooked food? I'm thinking of Ginza Fish, at 19 E. Ohio, where you could certainly sit and have a lesuirely chat in quiet surroundings. They're small, but they have a back area with booths where you could linger. The sushi is great, and their cooked dishes are also very good - I like the beef teriyaki, for example, and the tonkatsu. Don't be put off by the seedy Tokyo Hotel in the same building - Ginza itself is clean, cozy, and the food is pristinely fresh.
To throw out some more:
Bistrot Margot is my favorite french bistro in the city.
Blackbird and Avec have the same owners, and are quite good - Avec is the somewhat less adventurous (and cheaper) cousin.
Salpicon is excellent upscale Mexican food with a unique menu.
I also second a previous poster's suggestion of Kevin - I've been three times and have really enjoyed it every time.
Braserrie Jo is a nice choice and has an open floor plan - tables not packed together like you see in many Bistros. Its also near the mag mile, so it would be an easy walk through a busy neighborhood.
A few blocks farther to the west is Coco Pazzo - an upper tier, but still casual, Italian. Another good place for a leisurely meal. Excellent food and service, tables well spaced, and I have never felt rushed there over many visits.
Kevin has great food in a leisurely setting. I have never had a bad meal or a bad experience there. Also it helps that although it has excellent food, is usually isn't jam packed as some other places that deliver the same level of service or food.
Some other places I would recommend are Spring and Green Zebra.
I think I saw Avec recommended? As much as I love the food and atmostphere at Avec, not sure that under "normal" conditions, it can be classified as "leisurely" due to its communal seating and no reservation rule which always has people waiting in the entrance. If you want to go there and it be leisurely, I would say, you should go early or late on a weekday.
I like La Sardine (and their $25 prix fixe dinner on Tuesdays is a great value) but I'd hardly go there if I wanted to be assured of a "long, leisurely" conversation-friendly dinner (It's not called La Sardine for nothing). Brasserie Jo and Kiki's Bistro are two other dependable French bistros downtown with perhaps a more relaxed ambience.
I really recommend Avec for dinner. It has a sharable menu and the atmosphere is so relaxing-it feels like you're eating in a spa.
Go for a drink beforehand at Randolph Tasting Room...
And the Chocolate Cafe for dessert...
It is not clear what you mean by "great food," and how much you want to spend. Are you looking for a top drawer gourmet experience, or something more modest?
If you are looking for gourmet dining in a quiet restaurant, with leisurely service, I would recommend either Les Nomades or Everest. But both of these are quite expensive.
If you are looking for good food,in a quiet restaurant that will let you linger, I would recommend La Sardine in the West Loop. There are lots of other restaurants that would fit into this category too, but first you should give us more definition on how you are defining "great food," and what you are willing to spend for it.