Our dog walking hours are from 6am to 8pm 7 days a week, 365 days per year. Weekend Holiday Rates.Cancellations can be made up until your sitter has arrived. Even if you are operating your dog walking business as a sole proprietor, you should get a DBA (doing business as) or fictitious business name. Messaging - Chat with your walker or a member of the management team when needed. Easy Invoicing - View invoice history, make payments, or manage auto-pay. What is your cancellation policy? Our dog walking services ; DAILY DOG WALKING. New clients are required to fill out and keep up to date all client and pet information found on their Time to Pet profile via Client Portal. To become a dog walker in Chicago with Windy City Dog Walkers you must first fill out the online application.