Dog Walker/Cat Sitter

Windy City Paws

Dog Walker – Chicago

· $300 Dog Walker bonus after 90 Days*

· Work for Chicago’s Best Dog Walking Company, 2017 & 2019

· 7 Days a Week Dog Walker Support Staff Availability

We are currently hiring for multiple areas in Chicago: South Loop, West Loop, Streeterville/Loop, and Lincoln Park/Lakeview.

Windy City Paws is Chicago’s top-rated dog walking and petsitting company! In 2017 and 2019, Windy City Paws received the “Best Dog Walkers in Chicago” award from the Chicago Reader. We have been providing individual dog walks, dog runs, cat visits, and petsits in Chicago since 2009. We’re currently looking to hire a responsible animal lover to join our professional team! This position is eligible for a bonus after 90 days, see below.

A Windy City Paws dog walker and cat sitter must be committed to providing our customers the highest level of care and, most importantly, have experience with and love being with dogs and cats! This position is ideal for those who are looking for something outside the normal Monday – Friday, 9 AM – 5 PM, and enjoys variety and flexibility.

Dog Walker and Cat Sitter Responsibilities:

  • Providing consistent care and enriching playtime whether inside with cats or outside on walks with dogs for the full duration of the service time.
  • Prepare the dog(s) per household to go outside with the appropriate gear provided by the client.
  • Provide food, water, and medication as instructed by the client. NOTE: WCP provides training for any level of medication requested.
  • Picking up after pets outside on walks, scooping litter, and cleaning up any accidents in the home.
  • Be willing to commute to Windy City Paws service areas. If you have a car for commuting, that would be a plus!

Qualifications and Skills for this position:

  • Take on a dog walking route in a WCP Service Area.
  • Fully Available Monday-Friday; 10 am-4 pm
  • Must have occasional evening/weekend availability.
  • Be at least 21 years old.
  • Be comfortable being outside in all sorts of weather.
  • Have a smartphone or mobile device with WiFi and/or cellular data capabilities and daily internet access.
  • Intend to make this job a long-term commitment (6 or more months).
  • Pass a background check before starting the position.
  • Provide Covid-19 Vaccination & Booster Card


  • Starting pay during regular hours M-F 8 am-5 pm: $15.80/hr – $17/hr depending on relevant professional petcare experience.
  • Starting pay during evening & weekend hours (M-F 5-8pm & Sat/Sun 8am-8pm): $22.50/hr
  • A bonus of $300 after you complete your first 90 days with Windy City Paws, contingent on successful performance to date.*

 Dog Walker & Cat Sitter Benefits and Perks:

  • Enjoy the perks of being an employee!
  • Work for a company that cares about yoursafety!
  • Paid training when you onboard and continued education on dog and cat behavior and handling throughout your tenure with us!
  • Enjoy benefits like Paid Time Off and 401k paycheck contributions.
  • Work directly with the WCP’s Management Team. If you have a problem or need to give feedback, you’re dealing with a small team of great people.
  • Our online scheduling system lets you view your daily schedule and instructions/information for each pet.

Click HERE to view our video and learn more about dog walking for Windy City Paws!

Learn more about the benefits of working with a local business like Windy City Paws versus an on-demand app-based dog walking company!

Instructions to Apply:

If interested, please go to the following link to apply! 

To apply for this job please visit

Pay Rate/Range*: Starting pay during regular hours M-F 8 am-5 pm: $15.80/hr - $17/hr depending on relevant professional petcare experience. Starting pay during evening & weekend hours (M-F 5-8pm & Sat/Sun 8am-8pm): $22.50/hr