I had the distinct pleasure of dog-sitting for a night in the West Loop during one of 2014's most peaceful snowfalls. It was frigid, but the dog needed to be walked.
And so we went.
I realize you can't see the dog area in this picture, but there's plenty of room for them to scamper about in the dog enclosure just off to the right. I took this picture, first, because of the strange orientation of the stainless steel gates, and second, because it allowed me to get the Sears (Willis) Tower into the shot. The gates actually spray vaporized water for the warmer Chicago days. I was relieved that they weren't turned on because it was one of the two November days that dipped down into the single digits. But our boxer (Leia) didn't seem to mind. On our journey through the park we met quite a few characters, including an English Bulldog with no neck, and an overly-friendly Rottweiler approaching 160 pounds. Leia is well-known by most of the local dog-owners and they looked at my girlfriend and I with with skepticism. However, after assuring them that we were only temporary caretakers and not dognappers, they warmed up to us.
The West Loop is one of the more dog-friendly locations in downtown Chicago with parks like Mary Bartelme and stores like Paw Naturals and Wiggleyville Retail & Grooming. In 2014 alone there were three brand new construction rental buildings in the West Loop, each of them dog-friendly. Quite often when new buildings are in lease-up mode they will offer concessions like getting your first month free and waiving move in fees. Two of these building have in-building dog runs, just in case it's a little too cold to venture over to Mary Bartelme Park.