Yes. If you are a Daily Dog Walk client with a regular, recurring schedule with at least 3 service days per week, you are matched with a dedicated dog walker for your dog(s).

If your regular dog walker is unable to walk your dog due to illness or planned time off, it is Windy City Paws’ policy to seamlessly assign another walker on staff to walk your dog that day. We will notify you proactively of the change in walker for that scheduled service. You can also always view the dog walker scheduled to walk your dog in the online scheduling system. All Windy City Paws dog walkers are employees and trained to walk the Windy City Paws way. You will never have a backup dog walker who is anything less than a fully trained team member.

If you have an irregular schedule and use our Periodic Dog Walk service, you may not have the same walker each time.

Clients who maintain recurring scheduled service with three (3) or more service days per week are entitled to our Daily Schedule pricing. Scheduled services are defined as M-F, 8am-5pm with recurring days and times (ex: M/W/F 11am-1pm). For weeks in which a client receives services on fewer than three (3) days, the “Periodic” pricing will be applied to the services during that week.

To be eligible for Daily Dog Walk pricing, you must maintain a consistent schedule (recurring days and times) from week to week AND have at least 3 service days scheduled.

Clients who wish to schedule services in a more flexible way can onboard with Windy City Paws with the current Periodic pricing.

Why are regular schedules rewarded with lower pricing?

  1. To hire and retain the best talent, we need to offer consistent work. We offer lower pricing to incentivize clients to set a regular schedule because, when a dog walker’s clients cancel, they work fewer hours and get paid less.
  2. Our dog walkers are rarely able to pick up an extra service to compensate for cancellations. Most of our dog walkers have other jobs and life pursuits. Because our employees are of a higher caliber, they can find other forms of part-time consistent work if we are not able to offer it.
  3. Requests for non-recurring services require office coordination for each request.

Please view our Daily Schedule Pricing page for additional FAQs regarding this policy.

For our Puppy Package, we require a minimum of 10 regularly scheduled dog walks per week (2 walks per day) between the hours of 8am-5pm, Monday through Friday.

Face Masks: WCP employees must wear face masks where required and adhere to all building rules. Additionally, if you’d prefer your dog walker or cat sitter to be masked in your home for any reason, please just let us know and we’ll be happy to accommodate your request.

Hand Sanitizing: WCP employees are encouraged to sanitize before and after each service.

Positive Testing: Upon a positive test, WCP employees must notify the office and will have their walks reassigned until they may return to work per current CDC guidelines.

No Walk Socialization: WCP has always maintained a no-contact walk policy. We always avoid interactions with other people and dogs, and we do not visit dog parks.

No-Entry Handoff: If you are able to gear up and leash up your dog upon our walker’s arrival, the walker can take the dog from you with minimal contact and no entry to your home.

You will receive a push notification (if desired) and an email when your visit is completed. That notification will include:

  • A GPS verification of your service location
  • A photo of your pet(s)
  • Notes about the day's visit
You have two options. In your app, Time To Pet, you can send a private message to the office. You may also send a message directly to your dog walker with the office copied by default.

For Daily Dog Walk Clients: You have full access to your schedule through our online client portal and app. There, you can easily request new appointments and cancel existing appointments. You will receive an email confirmation when your request is confirmed.

We are happy to check availability and make any needed adjustments to your schedule whether it be days per week or timeframe so just email us at! Just give us at least a week's notice to give us time to check our availability and get everything updated on our end. Note these changes may result in a walker change. (Example: You currently have a M/W/F 12pm-2pm 30-minute walk schedule and you want to change that to a M/Tu/W schedule with the same timeframe and 30-minute walk.)

For Periodic Dog Walk Clients: Through our online client portal, you can easily request new appointments and cancel existing appointments. In order to meet periodic dog walk requests, we ask for at least 3 days' notice for the highest chance of accommodation but will do our best to accommodate requests with less notice. You will be contacted via email regarding your request.

Late Cancellations: You must submit your cancellation request by 5pm the day before a scheduled service or it will be considered a late cancellation and charged in full.

Daily Dog Walk Minimums: If the minimum number of full days of walks per week (3) is not met due to cancellations, the remaining walks for the week will be billed at published Periodic pricing.

We implement a cancellation policy for the benefit of our employees, who clear their schedules for your specific service timeframe. When cancellations are made prior to our deadline, our walkers and sitters can make other plans and take other jobs.

Daily Dog Walks:

If you have (1) scheduled dog walk per day, we require a 2-hour timeframe for the walker to arrive in. If you have (2) scheduled dog walks per day, we require a 1-hour timeframe for the walker to arrive in.

Periodic Dog Walks:

Periodic Dog Walks also have arrival timeframes. We always aim for a 2-hour window. However, for Periodic Dog Walks we may ask for a longer arrival timeframe in order to guarantee service.

Cat Visits:

Periodic Cat Visits: Sitters typically arrive consistently at the same time of day but we ask for an 8am-5pm time window for periodic cat visits. Evening visits can be scheduled if desired.

Daily Cat Visits: The service timeframe for daily cat visits is 10am-4pm. Evening visits can be scheduled if desired.


Sitters will arrive between 8am and 9am for a morning petsit and between 5pm and 6pm for an evening petsit.

All invoices and payments are made for services rendered. You are never paying in advance. When setting up your account, you will be enrolled in autopay and may use your bank account (ACH payment), Visa, Mastercard, or American Express. 

Clients who have recurring, regular schedules will receive an invoice via Time To Pet and be charged every other Saturday for the two preceding weeks of service.

Clients who have periodic, ad hoc schedules will receive an invoice via Time To Pet and be charged on the first of every month for the preceding month of service.

Yes. However, WCP observes the following holidays. On these days there are no regularly scheduled services unless specifically requested and approved. Services on these days will follow holiday pricing:

  • New Years Day
  • Easter
  • Memorial Day
  • Juneteenth (June 19)
  • Independence Day (July 4th)
  • Labor Day
  • Thanksgiving
  • Black Friday
  • Christmas Eve
  • Christmas
If you know a friend, family member, neighbor, coworker, or anyone else who needs regular dog walking services, send them our way! If they sign up for 3 or more regularly scheduled walks per week, we will give them $50 off their first 2 invoices and also credit your account $100 after their first month of service! Just remember to have them mention your name when they sign up!
Yes, we are bonded, insured and licensed in the city of Chicago. We can also provide prospective clients with copies of this documentation.
Office hours are Monday-Friday from 8am-5pm.

Please call us at 312.473.6466 with any questions you have regarding our areas of service.