Dog Walking in Old Town, Chicago
Old Town’s charming streets and quieter residential blocks make it one of the best neighborhoods in Chicago for dog walking — and Dogs Deserve It has been proving that for over 17 years. From the tree-lined paths near Eugenie Triangle to the historic Triangle District, our walkers know every corner of this neighborhood.
Old Town’s charming streets and quieter residential blocks make it one of the best neighborhoods in Chicago for dog walking — and Dogs Deserve It has been proving that for over 17 years. From the tree-lined paths near Eugenie Triangle to the historic Triangle District, our walkers know every corner of this neighborhood.
Old Town offers a unique blend of urban walkability and neighborhood calm. Our walkers take advantage of the quieter side streets for dogs who prefer a more relaxed pace, while using the Wells Street corridor for socialization-friendly walks with more activity.
With GPS tracking, real-time photos, and walkers who’ve been with DDI for years, your Old Town dog gets consistent, professional care from someone who knows the neighborhood as well as you do.
“We moved to Old Town with a nervous rescue dog. DDI’s walker was incredibly patient during the first few weeks, building trust at our dog’s pace. Now she practically drags us to the door when she sees the walker coming.”
— Jennifer L., Old Town
About Old Town
Old Town is known for its historic charm with cobblestone-feeling streets, boutique shops, and a quieter pace than its busier neighbors. Key landmarks include Eugenie Triangle Park, Second City, Wells Street shops, the Old Town Triangle District, and Stanton Park. Our walkers are deeply familiar with every block and know the best routes for dogs of all sizes and energy levels.
Our Dog Walking & Pet Care Services
Dogs Deserve It offers a full range of professional pet care services in Old Town, 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.