I stay in Chicago a fair bit and have come up with these two options - The Raddison Blue Aqua has a full gym with about 6-8 Cycleops bikes, which have powermeters. The problem I have encountered is that they aren't in very good shape. Often I have to hop from bike to bike to find one with a working powermeter and often the wattage calibration seems pretty off. The other option I have found in the Langham hotel (with a caveat that it is a pretty pricey hotel that I get a good corporate discount on). They have a nice gym with good spin bikes. No power but they keep the bikes in good condition.
+1 on the Raddison Blu Aqua - the Cycleops bikes were 300PTs - so you can't
use TranerRoad and other smart trainer software like you can with the later versions of this bike, but they do measure watts, and the flywheel is about 45 pounds
This hotel also has an outdoor running track, a 2-lane 25 Yard/(Meter?) indoor lap pool, and a 6 lane outdoor 25 meter lap pool (obviously closed this time of year).