Native Chicagoan here,
Although Plugshare has a respectable amount of information, it is far from inclusive. To answer your question, I don't know of any hotels that have a HPWC, although statistically most hotels use a shared garage, and nearly ALL the garages are lit up with a L2 charger or two. Anecdotally, they are usually filled with a Volt or Prius or something else that isn't really a full ICEing, but enough to annoy a 100% EV that really needs it.
So... to help out: First, remember the Tesla showroom at Grand Ave has a BUNCH of HPWCs outside for their vehicles, although I've never tried them. They are very welcoming, and I'm sure they'd let you stay there for a few hours. Also, if you look very carefully at the supercharge.info site, you will notice there are two secret supercharger slots there. They are often busy, but a very short trip outside downtown that can get you filled quickly. We also have superchargers on the interstates in all directions out of town.
The easiest third party network is Chargepoint... they have plans with no monthly charges and more expensive (read: emergency) L2 hourly options; EVGO is another that has I think 2 CHAdeMO options outside of a few additional Nissan dealers if you have one of those adapters.
Long story short, look around... there are plenty of options. We are a Tesla friendly state. :biggrin: