Neighborhood Dog Walker/Sitter

Windy City Dog Walkers
Chicago, IL

Company Overview:

Windy City Dog Walkers has been serving Chicago since 2002. We are a "dog walker-focused company" with excellent reviews on Glassdoor! We are an A+ company because we only work with A+ walkers, businesses, and clients. We focus on the needs of the walker and find you the best possible clients to build the job of your dreams. Many of our service providers prefer smaller neighborhood routes and enjoy the flexibility of choosing their own clients, hours, and availability. Our client's dogs thrive with the consistency of having a daily walker, and we find this system provides our walkers with reliable income that is more predictable when compared to other dog walking services or apps. If you love working with dogs and love working independently, this is the perfect self-employment opportunity you have been looking for!

Dog Walking Route Details:

We are currently looking for dog walking service providers to grow their own ideal routes in many of Chicago's neighborhoods. You will join our team as a self-employed 1099 contractor or independent business and choose a specific neighborhood (or two!) to work in. Our network of service requests will then be available to you to accept or deny, and grow your ideal dog walking job! Our dog walking service providers can work as little or as much as they like. It all depends on what services you choose to provide and what clients you take on. The majority of our service requests occur from 10 am to 4 pm, so it is very easy to build a client list of 8-12 individual walks per day, but you can also choose to work evenings, weekends, overnights, or any hours that are ideal for you. You have the opportunity to supplement your route with additional walks from other walkers who request assistance. Please keep in mind that pay can be lower in the first few weeks as you build your route and meet potential clients.

Job Summary:

This is a physical job designed for true dog lovers. You will be walking independently and tasked with keeping clients’ pets safe and following any instructions provided by the client. Ideal routes are normally within one neighborhood, but you will need to travel to multiple households during the day and provide your own transportation at your own cost (biking is a great, low-cost option!). Most dog walkers typically walk 5+ miles each day. We place great emphasis on safety, customer service, and self-reliance. Most walkers work an equivalent of 20-30 hours a week, but you can take on as many or few service requests or clients as you choose. Our walkers find the flexibility that our network provides to be an ideal way to stay independent and balance other jobs, clients, or school with the freedom of self-employment. To learn more about our opportunities, please check out our YouTube channel focusing on dog walking in Chicago.

Responsibilities and Duties:

  • Perform safe neighborhood walks on leash as directed by the client
  • Time management and communication to accept/deny service requests
  • Communicate with the office and clients via voice/text and email
  • Provide excellent customer service
  • Give all dogs attention, exercise, and care

Requirements:

  • No summer or short-term/seasonal positions are available
  • You must have a smartphone with a data plan
  • You must be at least 18 years of age
  • We prefer that you own a reliable source of transportation, such as an insured car or bicycle.
  • Public transportation and ride sharing are NOT viable options for covering a dog walking route
  • Be prepared for all weather conditions - you will be working outdoors
  • Legally authorized to work in the United States
  • Willing to submit to a background check

Qualifications and Skills:

  • Knowledge of dog breeds and behavior can be helpful, but is not required
  • The ability to make quick decisions to keep dogs safe
  • Capable of walking more than one dog at a time
  • Comfortable walking dogs with special medical or behavioral concerns
  • Time management is a critical skill to ensure on-time arrivals for all dog walks
  • Experience communicating with others via voice, text, and email

Benefits and Perks:

  • Highly competitive industry pay
  • Paid meetings/orientation with potential clients and their dogs before signing up for service
  • Bonuses paid for any walks performed with multiple dogs in a home or any optional non-peak hour walks (evenings, weekends, house sits, etc.)
  • Paid orientation process
  • Orientation completion bonus of $250. (A wonderful way to purchase transportation for the role!)
  • Casual dress code (dress for the weather without the need to wear a uniform)
  • Work within a fun environment that encourages learning with positive/animal-loving co-workers
  • Promotional opportunities with a highly rated/established company and others in our network

If you would like to learn more about our company culture and dog walking, please visit our website at:

Posted 2026-02-18

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