I very much do the same thing here in Big Shoulders. I have routes going to the north, south, and west sides, depending on which way the wind can blow me home. I try to mix up routes to get a look at fresh things while I am riding. Been pretty lucky no cars have veered off their paths and clobbered me from behind in my 20+ years of doing this on the streets of the city. And all it would take is one to end at least my riding career.
Some may say I should move onto the sidewalk to ride to get out of the way of drivers who have a legal right to the road over me, but doing so is statutorily illegal in this city, plus, I have all the same rights (and responsibilities) on the road as a car driver does.