Waldorf Astoria Chicago
Not Diamond but only Gold...
Booked a Deluxe room with fireplace as a reward night @95,000 points for Friday night two weeks ago.
Upgrade in the app showed a One Bedroom Suite with Balcony the night before - could select the 26th (highest floor) and received exactly that.
Very nice and large suite, view to the north with a glimpse of Lake Michigan. Location just great for walking the city. No problems having the Honors $50 credit applied.
Very happy overall!