Finally had a chance to stay at the Wit. I don't go to Chicago much & when I have in past I've stayed at the WA (which is often referred to as Hilton's best property in the USA). I can say that in my opinion the Wit was on par with the WA.

In all case at the WA & with my Wit stay I was upgraded to a suite so I can compare equal products.

The decor was different (wit more of a hip/modern look; WA more traditional/high end; both equally nice though your tastes may differ).

Without knowing specific sq ft, they both seemed equally spacious, though the WA offered a balcony & working fireplace while theWit had a kitchenette.

theWit gives you breakfast vouchers if you have status ($15 off the menu which basically covers any one meal order; or some set breakfast - I did the menu option); the WA has no breakfast perk.

theWit seemed 'busier' when checking in/out whereas the WA while not a small hotel never seemed busy (in a good way). Though of course as the dates were different it could have just been a dead weekend.

Location; this is subjective as for where you're going of course, but I found theWit better as it was more downtown plus right next to a CTA stop; the WA was a bit of a hike to one. In no way is the WA a bad location, just less convenient unless you have reason to be in the Gold Coast.

theWit has a rooftop deck that is a nice plus, though I found the crowd to not really be my style so nice to check out but didn't stay long (i will note that using the restroom at the bar there made me think it was made as the perfect stalls to do lots of coke in if you were into that sort of thing as they locked from floor to cieling with a glass shelf at head level, but I digress)

Staff was wonderful at the WA & adequate at theWit.

In summary, i understand why the WA is deemed high quality (though I wouldn't deem it anything overly special either & as its given such high marks in the US just goes to show how Hiltons lag here in comparison to their international products in my opinion), but when choosing I wouldn't hesitate to stay at theWit either & would in no way feel I was missing out on anything. With the points+cash option that pops up for theWit at times I think I would lean towards staying there if doing an awards stay as the premium the WA costs isn't really worth it in my opinion.