- Address 833 W. Chicago Ave, Suite 206, Chicago , Illinois, US
- Salary Offer 25$
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Job Overview
Windy City Dog Walkers is expanding its Chicago team and needs long-term 1099 dog walkers who love fresh air, flexible hours, and four-legged clients. Build a steady route in Lincoln Park, South Loop, Logan Square, West Loop, or the neighborhood you know best and earn up to $22.50 an hour, plus tips and bonuses.
You’ll work as an independent contractor: set your own schedule, walk on-leash dogs one-on-one or in pairs, log visits with our mobile platform, and keep pet parents updated. To qualify you must be 18 +, legally able to work in the U.S., own a smartphone and bike or car, pass a background check, and commit for at least a year. Expect to cover five-plus walking miles daily in all weather.
We provide paid orientation, route-planning help, client introductions, and a $250 start bonus once onboarding is complete—no algorithm drop-offs here. High-volume walkers see evening/weekend premiums, multi-dog surcharges, and referral rewards.
Ready to turn strolls into income? Apply online, meet us for a quick Zoom chat, finish orientation, and start taking bookings right away. Questions? Visit windycitydogwalkers.com and click “Join Our Pack.”
📍 Service Areas (Neighborhood-Based Routes)
We’re actively seeking Chicago dog walkers to manage neighborhood routes in:
- Lincoln Park
- South Loop
- Logan Square
- West Loop
- Other vibrant neighborhoods in Chicago
Each walker selects their preferred zones and builds their dog walking routes in areas they love and know well.
💼 Job Overview
Position Type: 1099 Contractor
Employment Model: Self-Employed / Freelance
Schedule: Flexible hours — weekdays, evenings, weekends
Category: Dog Walking & Pet Care
This contracted position is ideal for:
- Students seeking flexible work
- Outdoor job seekers
- Dog enthusiasts
- Freelancers looking for a consistent side hustle with dogs
🐶 Key Responsibilities
- Provide safe, structured, on-leash walks to client dogs in their neighborhood
- Maintain a consistent routine for assigned pets and ensure their safety at all times
- Communicate with pet owners via voice, text, or email
- Update service logs after every walk and report any health/behavioral concerns
- Accept or decline service orders through our platform
- Cover occasional evening, weekend, or holiday walks for off-peak incentives
🧾 Requirements
| Requirement | Details |
|---|---|
| Age | 18+ years |
| Legal Authorization | Must be legally allowed to work in the U.S. |
| Smartphone Required | Yes — with a valid data plan |
| Transportation Required | Car or bicycle preferred (no public transport or ride-share allowed) |
| Long-Term Commitment | Short-term or seasonal work not accepted |
| Physical Stamina | Capable of walking 5+ miles per day |
| Weather Readiness | Must be comfortable working outdoors year-round |
| Background Check | Required before onboarding |
🔑 Ideal Candidate Traits
We’re looking for individuals who:
- Are passionate about animal care jobs and enjoy working independently
- Can manage their own time and make their own schedule
- Are comfortable with all dog breeds, sizes, and temperaments
- Can walk multiple dogs simultaneously when needed
- Value long-term client relationships over short gigs
- Want to build their own dog walking route with stability and freedom
💸 Compensation & Incentives
You’ll be paid per service, with added perks to reward extra effort and performance:
| Payment Element | Details |
|---|---|
| Paid Per Walk | Variable depending on number of dogs and walk duration |
| Average Hourly Rate | Up to $22.50/hour for high-volume walkers |
| Tips and Bonuses | Yes — directly from clients |
| Off-Peak Incentives | Evening, weekend, and overnight premiums available |
| Multi-Dog Bonuses | Earn more for households with 2+ dogs |
| Orientation Bonus | $250 after completing onboarding |
| Client Referral Bonus | For every client you refer who books service |
| New Walker Referral Bonus | For every new walker you bring into the team |
🎓 Onboarding & Support
Unlike many app-based services, we offer:
- Paid orientation sessions
- One-on-one route planning support
- Client introductions and profile reviews
- A growing community of Chicago dog walkers
- Access to training tools and educational content
“You’re not dropped into an algorithm. You get real support, real people, and real growth.”
🌎 Why This Is More Than a Gig
This is a career in dog walking, designed for those who want to build a meaningful relationship with both dogs and humans. You’re not running errands—you’re providing companionship, safety, and enrichment to pets whose owners rely on your consistency and professionalism.
As a freelance dog walker, you’ll:
- Choose your availability and adjust it at any time
- Combine walks with pet sitting services for extra income
- Explore new neighborhoods in Chicago while staying active
- Enjoy the autonomy of self-employment with the support of an established team
- Take on as many or as few clients as you want
Whether you’re walking a Frenchie in South Loop, a Lab in Lincoln Park, or a rescue mix in Logan Square, each day offers a new adventure—and a real connection.
📹 What’s It Really Like?
Check out real walker experiences on our YouTube Channel:
🎥 Windy City Dog Walkers on YouTube
📝 How to Apply
Applying is simple and fast:
- Fill out our online application
- Join a brief Zoom interview to meet our team
- Complete your paid orientation
- Start building your dog walking business!
📈 Summary
If you’re ready to earn extra money, enjoy flexible hours, and thrive in a role that offers both independence and community, this could be the beginning of your long-term opportunity in dog walking. At Windy City Dog Walkers, you’re not just walking dogs — you’re creating connections, growing a business, and doing what you love.
🐾 Apply today. Join our pack. Walk your way to freedom.
