Reliable Dog Walking in Chicago Your Pup Will Love
Give your dog the exercise and attention they need with vetted, caring Chicago walkers. Get peace of mind with GPS tracking and photo updates.
Why Choose Tails for Chicago Dog Walks?
Midday Exercise & Relief
Ensure your dog gets the potty break and activity they need while you're busy.
Vetted & Trained Walkers
Every walker is interviewed, background-checked, and trained in safety protocols.
Personalized Attention
We match you with walkers suited to your dog's energy level and needs.
GPS Maps & Photo Updates
See the route map and get photos from every walk for complete transparency.
Simple Steps to Happy Walks
Booking reliable dog walking in Chicago is easy with Tails.
Share your dog's personality, routine, and any specific walking needs.
We'll suggest vetted, local Chicago walkers based on your profile.
Meet your potential walker beforehand to ensure a comfortable fit.
Easily book walks online and receive GPS maps and updates.
Create Your Pet Profile
Share your dog's personality, routine, and any specific walking needs.
Get Matched with Walkers
We'll suggest vetted, local Chicago walkers based on your profile.
Free Meet & Greet
Meet your potential walker beforehand to ensure a comfortable fit.
Schedule Walks & Relax
Easily book walks online and receive GPS maps and updates.
Care Tailored to Your Dog's Needs
Our experienced house sitters can accommodate a variety of special requirements to ensure your dog receives the best care possible in your absence.
Reliable Medication Schedules
Reliable administration of pills, injections, etc., precisely following your vet's instructions.
Gentle Senior Dog Comfort
Patient care focused on your senior dog's mobility, diet, and comfort needs at home.
Consistent Puppy Routines
Maintaining your puppy’s routine at home: play, training reinforcement, and potty schedules.
Calming Anxiety Support
Experienced sitters create a calm, secure environment in your home to help ease separation anxiety.
Skilled Behavioral Management
Safe, skilled handling for dogs with reactivity or triggers, following your guidance.
Dedicated Physical Needs Care
Attentive support for dogs with vision, hearing, or mobility challenges, ensuring comfort and safety.
Reliable Medication Schedules
Reliable administration of pills, injections, etc., precisely following your vet's instructions.
Gentle Senior Dog Comfort
Patient care focused on your senior dog's mobility, diet, and comfort needs at home.
Consistent Puppy Routines
Maintaining your puppy’s routine at home: play, training reinforcement, and potty schedules.
Calming Anxiety Support
Experienced sitters create a calm, secure environment in your home to help ease separation anxiety.
Skilled Behavioral Management
Safe, skilled handling for dogs with reactivity or triggers, following your guidance.
Dedicated Physical Needs Care
Attentive support for dogs with vision, hearing, or mobility challenges, ensuring comfort and safety.
Your Pet's Safety on Every Chicago Walk
We prioritize safety with thorough vetting, GPS tracking, and ongoing support.
Rigorous Walker Vetting
Includes ID verification, background checks, and interviews.
GPS Tracked Walks
Real-time tracking and route maps provide accountability and peace of mind.
Emergency Support
Our dedicated team is available for assistance during walk times.
Secure Platform
Safe messaging and payment processing.
Rigorous Walker Vetting
Includes ID verification, background checks, and interviews.
GPS Tracked Walks
Real-time tracking and route maps provide accountability and peace of mind.
Emergency Support
Our dedicated team is available for assistance during walk times.
Secure Platform
Safe messaging and payment processing.
A Better Walk Experience
Personalized Routes
Walks tailored to your dog's preferences and energy levels.
Real-Time GPS Tracking
Follow along with the walk via a map on your app.
Consistent Routine
Reliable walkers help maintain your dog's schedule.
Instant Updates & Photos
Receive notifications, photos, and a report card after each walk.
Your Chicago Dog Walking Questions Answered
Reliable Dog Walking Across Chicago
Find trusted walkers in your neighborhood, including:
What Chicago Dog Owners Say About Our Walks
"Tails has been a lifesaver for midday walks! Luna comes back happy and tired."
"Love the GPS tracking and photos. I always know Max had a great walk with his walker."
"So reliable and easy to schedule. Our walker is fantastic with our energetic pup!"
Give Your Dog the Best Walks in Chicago
Join the waitlist for access to vetted, reliable dog walkers in your neighborhood.
Caregivers matched to your dog's energy level, age, and needs
GPS tracking and real-time updates during every service
Simple scheduling for walks, boarding, and daycare
Priority Matching
For Early Access Members
Waitlist members get first access to our top-rated caregivers and premium time slots when we launch in your neighborhood.