I find this post funny, only b/c I'm thinking it sorta matters where they're coming from, how sophisticated their palate may be and how comfortable they would be in certain settings. I've been saying in my own position, if my Japanese in-laws (particularly brother-in-law) ever makes it to Chicago, one of the places I'm going to take them is.... Medieval Times... Think of all the crazy stuff they'll have to tell everyone they know when they get back. My brother-in-law is always fascinated by armor, weapons, etc whenever he visits museums; I think he'd get a kick out of the cheesiness of Medieval Times, eating a whole rotisserie chicken with his hands and drinking it up with pitchers of cheap brew while cheering on our knight. I have flashbacks of The Cable Guy w/ Jim Carrey as I write this... damn funny stuff... Yeah... Medieval Times for sure... and then a nice steak house...

I'd take my dad to Medieval Times if I didn't want to make it to Sunday. =)

They're kinda difficult. For Mother's Day a few years back I took my mom to Tru (even sat at the chef's table). Seeing her eat bone marrow was priceless. But my dad would not only hate the food, he just can't deal with the price. So it's always a trick to find 1) good food, 2) classy with good service and not "bustling", 3) not too aggressive cuisine, 4) not so boring i fall asleep.

Osteria via Stato used to fill the bill nicely, but the last two meals I had there were pretty disappointing. We used to love the place.

basis wrote:But my dad would not only hate the food, he just can't deal with the price.

In your original post, you said up to $500 for four was OK. Upwards of $100/person is pricey in my book! (But I realize not in everybody's--your Dad's threshold must be higher than that. More power to him!)