The Drake was built in 1920 as an elegant hotel with beautiful flourishes and spacious rooms. Too bad Hilton doesn't invest in the remodel this grand dame deserves.
I would stay at The Drake again simply for the memories from my wedding night (29 years) and the nostalgia it evokes for more glamorous eras. For this, I tolerate the faded wallpaper, cheap furniture and lighting, and outdated bathroom with a flooding shower tub.
On the positive side, housekeeping is great, breakfast is good, the hall carpeting was colorful and new.
Best of all, you can't beat The Drake's lakefront location!