No, I don't know the names of any of those, but I'd like to -- if you will share.
I've stayed in a hotel with my dog before, but it was during a move and it was only a few days. Wisconsin is not too friendly about dogs -- they cannot be in a place where food is served, or so I'm told. We had a catered lunch at a Dog Rescue society function I attended in December, and all the dogs had to go sit in the cars when lunch was served. And it was COLD outside!
My understanding is that Chicago ordinances do not prohibit a dog accompanying its owner at an outdoor cafe, leaving it to the individual establishment to set its own policy. A web search under "dog friendly chicago" is helpful, but beware that the information may be outdated.
As for hotels, I recommend the Palmer House or the Hotel Monaco (both are in the Loop). Be sure to cash-in your Krugerrands before you go. Again, beware . . . most dog-friendly hotels only allow small dogs. Call to verify.