Dog Walking in Wicker Park, Chicago
Wicker Park’s creative, independent spirit extends to its dog owners — and Dogs Deserve It has been serving this neighborhood for over 17 years. The actual Wicker Park green space is one of the best dog-watching spots in the city, and the 606/Bloomingdale Trail offers an incredible elevated walking route that our dogs love.
Wicker Park’s creative, independent spirit extends to its dog owners — and Dogs Deserve It has been serving this neighborhood for over 17 years. The actual Wicker Park green space is one of the best dog-watching spots in the city, and the 606/Bloomingdale Trail offers an incredible elevated walking route that our dogs love.
Our Wicker Park walkers know the rhythm of this neighborhood. The quieter morning streets, the bustling afternoon sidewalks along Milwaukee Avenue, the best entrances to the 606, and which blocks have the friendliest dogs for socialization. We rotate routes to keep your dog engaged and mentally stimulated.
GPS-tracked walks with real-time photos mean you can follow along from your studio, office, or coffee shop. Your dog’s walk is the best part of their day — and we make sure of it.
“Our walker takes our husky on the 606 trail almost every day and the photos are incredible. DDI treats our dog like family. After 17 years in business you can tell they actually care — it’s not just a gig for them.”
— Maria G., Wicker Park
About Wicker Park
Wicker Park is known for its creative energy, independent shops, and a mix of longtime residents and newer arrivals who all love their dogs. Key landmarks include Wicker Park (the actual park), the 606/Bloomingdale Trail, Milwaukee Avenue, Division Street, and the Flat Iron Building. 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 Wicker Park, 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.