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OP I don't have dogs but I do have cats. I'll be honest I have always just used Rover. I don't go out of town much so I don't need someone who comes consistently or anything. When I do go out of town I just find someone on Rover. It seems like they are a really relaible site for finding petsitters.
Check out greenpawschicago. They are true animal lovers and will work with you on what works best for you and your fur baby's situation.
I have a friend who lives in Lakeview who dog sits and picks up dogs to dog sit so the distance wouldn't be a problem.