All-you-can-eat Brazilian churrascaria for ~$50. Try every steak they bring you, try the chicken hearts (once, and never again), and demand they bring out some grilled pineapple.
My favorite mid-priced sushi place near Palo Alto. They don't take reservations so plan for 30 minutes to an hour walking around Castro.
I've never been to Chicago but these pizzas are pretty damn good. There can be a bit of a wait in the evening though.
Yummy breakfast/brunch. Ignore your dining partners, read the funny menu, gawk at the oddball artifacts. Netscape and PayPal were funded here. Hotmail was founded here. Yahoo! almost started here.
