$500 pp for this doesn't sound that outrageous. You figure a six course dinner for something like this would be minimum 150. Big question is the wine. If the wine selection is good, could be worth another 150. Then you get the friday night thing, the class, and brunch. That feels like another 100+ and then factor in hotel/private element of it and yeah it doesn't seem outrageous. Now that doesn't mean it's everyone's cup of tea. But compared to $200+ for an hour massage or $400+ for the falconry this is downright reasonable.

FWIW, Longman & Eagle is legit. One of my favorite places in Chicago. Much more high end and creative gastropub food vs fine dining. But very high quality. Now if only they could bring the mixologist and the beer list from L&E...