Meet before you book
See how your dog responds. Book only when you're sure.
Boarding
Cozy overnight care with photo updates. Your pet gets belly rubs, treats, and lots of love!
Learn more →Dog Walkers & Pet Sitters · Chicago
Sarah K.
4.9 (127)
Sarah K.
4.9 (127)
Dog Walkers & Pet Sitters · Chicago
Know who's right
for your dog—
before you book.
We match by breed, energy, and personality. You'll see exactly why — with reviews from owners whose dogs are just like yours.
Free to match. No subscription required.
How Matching Works
What makes them right for your dog?
You shouldn't have to read 47 profiles to find someone your dog actually likes.
Mark T.
★ 4.9 (127 reviews)
Lincoln Park Why we matched you
Knows how to tire out a Golden
Keeps 50+ Golden families coming back with runs that safely tire out dogs who need serious exercise.
"Max came back exhausted and happy every time. Finally someone who wears him out."
— Tom R., Golden Retriever · Lakeview
Maria L.
★ 5.0 (89 reviews)
Wicker Park Why we matched you
Knows how to read a senior dog
Cared for 30+ senior dogs. Keeps walks gentle, watches for mobility issues, and never rushes.
"My 12-year-old Lab loved Maria. Let him sniff and go at his own pace."
— Jennifer K., Senior Labrador · Bucktown
Maddie M.
★ 4.8 (156 reviews)
Logan Square Why we matched you
Turns anxious dogs into excited ones
Helped 40+ nervous dogs feel safe with calm, predictable routines.
"My Chihuahua was scared of everything. Now she gets excited when Maddie arrives."
— Lisa M., Chihuahua · Humboldt Park
See who we'd match with your dog.
See The Proof
You'll know where they walked.
What they ate. When they pooped.
Meet first, track walks, and get care reports.
Track your walks
42
Total walks
18.72 mi
Distance
14h 10m
Time
You've walked
42 times in February!
Every walk, verified
GPS route, exact distance, and a report when they're done. No guessing.
Know what happened
Photos and a full care timeline after every visit.
Why You Can Trust Your Match
Every provider earns their spot.
We interview over coffee, verify skills, and let your dog decide.
1
Real In-Person Interviews vs. Simple Background Checks
2
Verified Pet Care Skills vs. Unproven Claims
3
Backup Coverage vs. Being Left to Scramble
4
Free Meet-Up vs. Booking Sight Unseen
Real In-Person Interviews vs. Simple Background Checks
We interview every provider over coffee to understand how they handle anxious dogs, high-energy breeds, and reactive behavior — not just whether they cleared a background check.
Verified Pet Care Skills vs. Unproven Claims
Reviews cover what actually matters — how providers handle separation anxiety, leash reactivity, and first-time dogs. Not just star ratings.
Backup Coverage vs. Being Left to Scramble
If your provider cancels, we find a replacement — fast. You'll never be left scrambling the morning of a booking.
Hey, just saw I matched with your dog — want to meet before we start?
yes please. fair warning — she absolutely loses it when she meets new people, but calms down fast
Meet & Greet with Helena
Starts at: 09:00 AM 
Lincoln Park, Chicago, IL 60614 Free Meet-Up vs. Booking Sight Unseen
See how your matched provider bonds with your dog during a free meet-up before you book.
Getting Started
From download to first walk — in 48 hours.
No endless scrolling. No awkward cold messages. Just a match, a meet, and a booking.
1
Tell us about your dog
Breed, energy level, temperament, special needs — the stuff that actually matters for finding the right fit.
2
See your matches and why
We show you providers matched to your dog's specific needs — with the reasons behind each match.
3
Book a free meet & greet
Watch your dog meet their caregiver in person. Only pay when you're ready to book.
Our Services
What does your dog need?
Walking
Energizing walks tailored to your dog's needs. From quick breaks to adventure trails!
Learn more →
Day Care
Supervised play and socialization while you're away. Fun, exercise, and plenty of attention!
Learn more → 
What a good boy! Here's a yummy treat for you!
Cozy overnight care with photo updates. Your pet gets belly rubs, treats, and lots of love!
Learn more → Now Available on iOS
The
Right Caregiver
For Your Dog's Unique Needs
Download Tails to connect with vetted, background-checked pet care providers 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
Free to download. No subscription required.
Privacy Policy
Frequently asked questions
Couldn't find what you were looking for? We're here to help! Send us an email and we'll get back to you quickly.
Send EmailOur invite-only approach lets us find the best-of-the-best through word of mouth. Then, we personally interview every provider over coffee, verify their experience with specific pet behaviors like separation anxiety. We don't believe that passing a basic background checks is enough to qualify caring for our pets... or yours.
Three key differences: 1) We personally meet and test every provider (most platforms don't), 2) We match based on your pet's specific needs rather than making you scroll through hundreds of profiles, and 3) We offer free meet & greets so you can see how your pet responds before booking.
We create a profile that outlines specific traits about your dog's personality and care needs, then match them with providers who have proven experience with those exact traits. This eliminates the frustration of endless scrolling and ensures providers know how to handle your pet's specific quirks.
That's exactly why we offer free meet & greets with no obligation! If your pet doesn't seem comfortable, we'll match you with a different provider at no cost. We'd rather find the perfect match than force a booking that doesn't work for your pet.
Our providers send real-time photo updates during the visit, tracking of walks, detailed notes about your pet's mood, behavior, eating, bathroom breaks, and any special moments. Reports are delivered instantly so you always know how your pet is doing.
Tails only charges Providers 10% vs. industry norms of 20%-40%. This means providers on Tails earn more than on other platforms. You set your own rates, create your own schedule, and build a loyal client base that stays with you. Top providers can earn $800-1,500 weekly with consistent bookings.
Booking insurance is coming soon. We can also help pet parents buy pet care insurance and pet care providers buy pet sitter insurance.
Couldn't find what you were looking for? We're here to help! Send us an email and we'll get back to you quickly.
Send Email