I last stayed there in April, 2002. The rooms on the Hhonors floor are average or better in size - the last one I had featured some sort of exercise equipment that looked like a big elastic band.
I had an evening layover in ORD and so I took the blue line subway to downtown for $1.50. It takes about 45 minutes, but otherwise your food choices are somewhat limited at the airport. My employer paid for the cab ride back which was $30, and took about 25 minutes at 11PM.