Can you narrow down a splurge evening?

Every December my partner and I go out to celebrate a birthday with a walk around the downtown area (window watching, enjoying the holiday scenes) then a dinner out. My favorite experience was at Avenues back in the GEB days - great service, great wines (Aaron was there at the time), great food and a lovely view out the window to the lights below. I'm looking for a nice balance of warm, inviting atmosphere (so not Blackbird, as much as I like the food), great food, a quieter space (so not Nellcote, as much as I've enjoyed it, for example) and perhaps a great view of...something.

We've enjoyed North Pond and Spiaggia many times, so they are options.

We've never been to Everest, partially because in the yin/yang of Italian vs. French food I tend toward The Boot and its vegetables and starches over France and its meats and heavier sauces. OK, I know that's a generalization. We get stuck in our ways sometimes, right?

Sixteen, Pelago, Tru have all been suggested to me, though I've never been. Service is a component here as well - knowledgeable servers who enjoy talking about food and wine are always a plus. I'll never forget the server at...an unnamed local restaurant...who went back to check out my question of, "These microgreens taste fascinating, but what are they? Arugula?" He came back and said, "Nope, they aren't arugula. They're microgreens."

Cost isn't an option, as it's a once a year thing. Thoughts?

Spiaggia
North Pond
Tru
Sixteen
Pelago

Of the places you mention, the only one I've managed to get to is Everest.
Food was very, very good, but a little stuffier, less playful than you may find elsewhere.
I did not find the sauces heavy: it's not nouvelle one-pea-and-one-slice-of-meat light, but it's not going to send you home feeling bloated either.
The view is amazing, though -- a romantic event kind of place.

I would do Tru. The place is like a different restaurant ever since Tramanto left and Anthony Martin fully took over the kitchen. Perfectly executed, inventive food, and service that's always been among the best in Chicago. No view, other than the art, but you're just around the corner from Michigan Ave. if you want to go for a walk, carriage ride, etc.

Thanks for both of your opinions. I've heard "stuffy" applied to Everest more than once, which also has kept me away. And I have wondered what Tru was like minus Tramanto.

I wouldn't call Everest stuffy, and have always found the staff friendly and warm, but the service is more formal than other places I have been to.

I'd give Everest a shot. The view is priceless, and the service is first class, and very, very well informed. Here are the menus, should you want to step outside your customary fare just a bit.

I've been to all you listed in the last 18 months other than Spiaggia. I'd go with Tru. IMHO, best restaurant in the city (other than Alinea).

Thanks for everyone's tips. I think we'll go to Tru! Now I owe a report to LTH.

You mentioned that you like a good view...of something. In this case it would be their art (which is why the room is a bit austere) You may want to check out their site beforehand to learn a bit about some of the artists. http://www.trurestaurant.com/art

Also, the service is very formal. They are happy to engage in conversation once you initiate.

Tru is wonderful... the kind of service that makes you feel comfortable. Save room for the cheese course-- my husband still talks about the Epoisse and we haven't been there for about 8 years. Can't wait to vicariously enjoy your experience...

Cheers, Jen

We have enjoyed NoMI in the Park Hyatt as a splurge restaurant, the restaurant is beautifully decorated, the view of Michigan Avenue is charming and the food is pretty terrific as well.

The view from Sixteen blows everything else out of the water. You look at the best parts of the Tribune Tower and Wrigley Building, and down the river to the lake. Next best is probably NoMI, then Spiaggia. The worst thing about Sixteen is the jackass behind the Trump Tower, but the building is great as is the restaurant in my experience. Everest, while high up, is not such a great view. Maybe I'm jaded after working in office towers my whole adult life. For what you are looking for, Sixteen might well be the best bet in terms of food, view, and proximity. I like Pelago, but it is very expensive for what it is, small and I'd say cozy and romantic. If you really like Spiaggia, you might give Pelago a try. I prefer the same team's new Japanese place, Masaki, which is tiny, comfortable and beautiful and steps from Pelago (also neear Tru), but with no view.