Where should I send my parents for their 30th anniversary?

My parents are coming into town and I want to send them to a nice restaurant for their 30th anniversary. Since it's their anniversary, I'm just going to send them and not tag along.

I'm looking for advice in a couple of areas
1) Where should I send them? I'm looking to spend about $300 for the two of them (A little higher is fine). Only one of them will be drinking. Also, I can't do something too out of the way because I don't want them to get lost. I was thinking Bonsoiree but I think it would be just a bit too hard for them to find. Ideally, it would be somewhere near the loop/river north/fulton market/gold coast area.
2) This isn't specifically about the food, but how does anyone have experience paying for someone else's meal when you aren't present? Do I just call them up beforehand and ask them to put it on my credit card?

I'd really love advice on either point.

Thanks!

In response to question #2: call the restaurant (or show up in person) to set it up in advance, then call again a bit before the reservation to confirm that it's all setup, then call again the evening of the reservation to reconfirm that it's all setup.

The reason I recommend calling so many times to make sure everything is setup & that the restaurant is well aware of your plan is that, 8 months after our wedding, my wife took me to Alinea for my birthday. Some very good friends of our caught wind of our impending dinner, and hatched a plan of their own - after our meal, the bill folio would be delivered to us. Inside, instead of the bill, would be a card with a message saying something along the lines of "We hope you enjoyed our wedding gift to you! Love, Your Friends". How cool is that?! Alinea told them, "No problem, it would be our pleasure", so our friends went down there a week beforehand and gave them the greeting card and their credit card info.

The night of our reservation, we went, enjoyed a magnificent meal, and at the end, we were presented with...our bill, which we happily paid. A week later, we saw our friends, and they asked us (with sly grins), "So, how was Alinea?" And my wife & I both answered, "It was great...why?" They then realized that their plan had failed. A week after that, they presented us with the original greeting card - after stopping by at Alinea to pick it up and give them a piece of their minds - and a very generous Chopping Block gift card.

Moral of the story: You might want to consider just buying your parents a $300 gift certificate to whatever restaurant you end up choosing. Or a Chopping Block gift card - we loved ours.

Edited to fix poor BBcode tagging

How about North Pond? Perfect setting and great food. The patio is exceptionally nice, especially with the cooler weather...

Thanks for the advice! I will definitely try calling up whatever restaurant I choose. I want to avoid gift cards as much as possible, although I may go that way. I'd like to leave money out of it as much as humanly possible, but of course, it's a restaurant so they're probably going to know how much it costs anyways.

North Pond seems like a good idea. I've never been there but I've heard that the atmosphere is top notch. I'll definitely look into it.