Part-Time Dog Walker-- Weekends and/or Flexible Weekdays

Flexible Dog Walking Job for Creative Professionals
Join Windy City Paws – Chicago's Top-Rated Pet Care Team

Are you a creative spirit who also happens to love animals? Whether you're a freelance illustrator, musician, dancer, actor, or in-between gigs, Windy City Paws offers a meaningful and flexible part-time job that fits into your artistic lifestyle.

We’re Windy City Paws—a professional dog walking and cat-sitting company serving Chicago since 2009. We pride ourselves on dependability, compassion, and keeping tails wagging (and cats purring) every day.

About the Role

We're hiring part-time dog walkers to join our professional W-2 team. If you're looking for a steady side income, time outside, and real connection, with both pets and people, this is a great fit.

This is not gig work. You'll be a trusted member of a team that never cancels on clients, with the training, support, and structure you need to succeed.

Availability Requirements

• Weekdays: At least 2 consistent days/week with some availability between 8am–4pm, OR 3 flexible weekdays if not consistent

• Weekends: Some late afternoon/evening availability

• Must be able to commit for at least 3 months

Why Artists Love Working with Us

• Flexible scheduling that works around rehearsals, studio time, or auditions

• Time outside and physical movement—clear your head, stay active, and get inspired

• A chance to decompress between creative gigs by bonding with animals

• Consistent income, even when creative work fluctuates

• Connect with a community of animal lovers

Job Details

What You'll Do:

• Walk dogs (30–60 minutes), play, and provide food/water/medication as needed

• Communicate with clients through updates and photos

• Build strong bonds with regular clients—both human and furry

• Clean up after dogs indoors and outdoors

• Be a calm, positive presence for pets during visits

What You Need:

• A vehicle or bike for reliable travel between visits

• Smartphone with data for communication and walk tracking

• Physical ability to walk outdoors in all seasons for multiple hours per day

• Open to key pick-ups/drop-offs when needed

• Strong communication and reliability—your clients (and their pets) depend on you!

Pay & Perks

• Paid per walk (based on visit length and neighborhood)

• Typical weekly earnings: $100–$150 (~5–10 hours/week)

• W-2 employment, not independent contracting

• Paid Time Off (PTO) and 401(k) contributions after 6 months

• Ongoing paid training in animal care and behavior

Service Areas

South Loop, River North, West Loop, Streeterville, Gold Coast, Old Town, Lincoln Park, and more.

Make Your Side Job Meaningful

If you're looking for part-time work that won’t drain your creative energy—and may even refuel it—apply to Windy City Paws. Help animals, support pet parents, and enjoy the rhythm of life on foot.

Apply today and start walking with purpose!