Working at Windy City Dog Walkers | Glassdoor

Windy City Dog Walkers Overview

Chicago, IL
Company - Private
Health, Beauty, & Fitness
Unknown / Non-Applicable
Windy City Dog Walkers offers dog walking and pet care services in many Chicago neighborhoods. We are licensed, bonded and insured and have been dedicated to the highest level of professionalism in pet care since 2002. Our walkers are experienced animal lovers and excited ... Read more

Mission: We offer daily dog walks, cat care, and pet sitting with an emphasis on personal attention to meet any of your dog walking or pet care needs. We provide the same dog walker every day to ensure the best possible service and consistency for each client. We do not group walk with ... Read more

Windy City Dog Walkers Reviews

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  • "Great experience; great management team"

    • Work/Life Balance
    • Culture & Values
    • Career Opportunities
    • Comp & Benefits
    • Senior Management
    Former Contractor - Dog Walker in Chicago, IL
    Former Contractor - Dog Walker in Chicago, IL
    Positive Outlook

    I worked at Windy City Dog Walkers as a contractor (Less than a year)


    Windy City is a growing dog walking company with a well-established reputation locally, so there are tons of client opportunities to work as much as you want. Some clients have been with the company for years and you can build a good relationship with them and the dog. Management team was amazing, always very responsive and caring for employees. Very respectful of walkers scheduling decisions. Schedule itself is super flexible, easy to design your own hours with many opportunities for additional weekend/evening hours. Management was also very knowledgeable and responsive to any questions or concerns about dog walking, training, and behavior.


    Client cancellations can make scheduling at times unpredictable, but there were almost always opportunities to make up these missed walks and you are still paid for any last-minute cancellations. Depending on the walker, the job itself can be physically strenuous, especially if you have a full schedule for the day. Also, sometimes your schedule can be over-booked due to the high demand. However, management team or other walkers are almost always able to help out if a day is too full.

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Windy City Dog Walkers Photos

Windy City Dog Walkers photo of: We service Wicker Park which is a great opportunity to be social with your dog!
Windy City Dog Walkers photo of: Our dogs love visiting the Chicago Riverwalk.
Windy City Dog Walkers photo of: Dominic & Huck are old friends. We have some of the longest work periods of any dog walking company in Chicago. We have long term clients as well!
Windy City Dog Walkers photo of: We offer a variety of schedules from part time to full time.
Windy City Dog Walkers photo of: Dog walking is a fun job, especially when most of your day is spent in one of Chicago's beautiful parks!
Windy City Dog Walkers photo of: Dog walkers earn a bonus with clients that own more than one dog.
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Windy City Dog Walkers Interviews



Getting an Interview

Getting an Interview





    Dog Walker Interview

    Anonymous Employee in Chicago, IL
    Accepted Offer
    Neutral Experience
    Average Interview


    I applied online. I interviewed at Windy City Dog Walkers (Chicago, IL) in December 2013.


    There was a phone interview first, and then an in-person interview with the owner. He asked very typical questions that I have heard at other interviews. Overall it was a very average interview.

    Interview Questions

    • How would you handle a situation with a dog trying to be aggressive toward you?   Answer Question
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Windy City Dog Walkers Awards & Accolades

  • Best of Chicago, Chicago Reader, 2014

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