Dog Walking in Boystown, Chicago
Boystown and the surrounding East Lakeview area are home to a tight-knit community of dog lovers — and Dogs Deserve It has been part of that community for over 17 years. Our walkers are a familiar sight along Halsted and Broadway, providing reliable daily walks rain or shine.
Boystown and the surrounding East Lakeview area are home to a tight-knit community of dog lovers — and Dogs Deserve It has been part of that community for over 17 years. Our walkers are a familiar sight along Halsted and Broadway, providing reliable daily walks rain or shine.
This neighborhood’s walkability is a huge advantage for dogs. The grid of residential streets between Belmont and Addison offers endless route variety, and our walkers rotate paths to keep your dog mentally stimulated. We know which buildings have dog-friendly lobbies, where the best fire hydrant stops are, and how to navigate the busier commercial stretches safely.
Every walk is GPS-tracked with real-time updates and photos sent directly to you.
“I work long hours and used to feel guilty about it. DDI completely changed that. My dog gets a proper 40-minute walk every day with someone who genuinely cares about him. The daily photos are the highlight of my afternoon.”
— David R., Boystown
About Boystown
Boystown is known for its vibrant, welcoming community with colorful streets, local shops, and a strong neighborhood identity. Key landmarks include Halsted Street, Broadway, the Belmont CTA station area, Mariano Park, and Roscoe Village border. Our walkers are deeply familiar with every block and know the best routes for dogs of all sizes and energy levels.
YOUR AREA WALKER, JACK
I was born and raised in Kansas City, Missouri. Moved to Chicago in 2019 and have been working at DDI since 2020. Outside of work I enjoy Biking, watching football, and playing intramural sports. I’ve been taking care of various animals my whole life. I look forward to meeting you and your dog!
Our Dog Walking & Pet Care Services
Dogs Deserve It offers a full range of professional pet care services in Boystown, backed by 17 years of experience, GPS-tracked walks, and W-2 employed walkers with outstanding tenure.
🐕 Daily Dog Walking
- 15-minute walk — starting at $25/walk (package) or $30 (as-needed)
- 25-minute walk — starting at $31/walk (package) or $37 (as-needed)
- 40-minute walk — starting at $39/walk (package) or $47 (as-needed)
All walks include GPS tracking, real-time updates, and walk photos. Package pricing requires 3+ recurring daytime walks per week.
🐶 Puppy Visits
Customizable puppy services for dogs under 6 months — exercise, potty time, feeding, and playtime. 1-hour preferred arrival window. Starting at $26/walk (15 min) or $32/walk (25 min).
🏠 Pet Sitting
- Overnight pet sitting — $135/day (up to 3 walks/day on your dog’s schedule)
- Hourly pet sitting — $40/hour
- Holiday pet sitting — $180/day
🐱 Cat & Critter Care
Cat sitting, rabbit care, fish visits, and plant watering available. Starting at $16/visit.
🚗 Pet Taxi
Transportation to and from vet appointments, groomers, and daycare. One-way $35, round-trip $55/hour.
Why Dogs Deserve It?
- ✅ 17 years in business — Chicago’s most experienced dog walking service
- ✅ 400,000+ walks completed
- ✅ 100+ five-star Google reviews
- ✅ W-2 employees — not independent contractors. Background checked, insured, and trained.
- ✅ Outstanding walker tenure — our walkers stay for years, building real relationships with your dog
- ✅ GPS-tracked every walk with real-time updates and photos
- ✅ Pet CPR certified — every walker
View all services and pricing →
Serving All Chicago North Side Neighborhoods
Dogs Deserve It proudly serves Lincoln Park, Lakeview, Boystown, Old Town, River North, Wicker Park, Roscoe Village, Lincoln Square, Logan Square, Bucktown, West Town, North Center, and River West.