See your dog's perfect match. We pair you with Old Town providers based on your dog's unique needs.
Dog Walking in Old Town typically costs $25-$35 per walk . Tails matches you with background-checked providers based on your dog's unique needs—size, energy level, and personality.
All parks require a Dog Friendly Area (DFA) permit ($10/year). Our walkers ensure compliance.
630 N Kingsbury St, Chicago, IL 60654
2645 N Sheffield Ave, Chicago, IL 60614
East-west streets channel lake wind ("The Hawk") from nearby lakefront. Victorian buildings provide some wind shelter on residential streets. Wells Street commercial corridor has heated entries and awnings. High-rises have indoor dog relief areas but vintage walkups do not.
Note: This area is affected by Chicago's winter parking ban. Our walkers navigate accordingly.
Dog Walking in Old Town typically costs $25-35/walk. Prices vary based on duration, number of pets, and specific requirements. All Tails providers are background-checked and insured. See our 2026 pricing guide for more details.
Yes. All Chicago off-leash dog parks require a $10/year DFA (Dog Friendly Area) permit. The fine for non-compliance is $500. Your dog must have current Rabies, DHPP, and Bordetella vaccinations. Tails walkers ensure your dog only visits DFA parks if properly permitted.
East-west streets channel lake wind ("The Hawk") from nearby lakefront. Victorian buildings provide some wind shelter on residential streets. Wells Street commercial corridor has heated entries and awnings. High-rises have indoor dog relief areas but vintage walkups do not. Tails walkers in Old Town are equipped for winter conditions, carry paw balm for salt protection, and adjust routes based on conditions. They also navigate around Chicago's overnight winter parking ban zones. Learn more in our Chicago winter walking guide.
Popular DFA parks near Old Town include Ward (A. Montgomery) Dog Friendly Area, Wiggly Field (Lincoln Park). Some parks have separate small dog areas. All require a valid DFA permit ($10/year).
Download the Tails app, enter your Old Town address, and browse verified providers. View profiles, read reviews, and book directly. All providers are background-checked, insured, and trained. You can message providers before booking and receive photo updates during service.
Traffic Level
medium
Walkability
excellent — wide sidewalks, short blocks
Street Cleaning
Varies by block - check posted signs. Residential typically Wednesdays or Thursdays 9AM-1PM (Apr-Nov)
Winter Parking
Affected by 2"+ snow ban (3AM-7AM)
See your dog's perfect match. We pair you with providers based on your dog's unique needs.