✦ Dog boarding, walkers, and sitters · Chicago
Find the best
dog walker
or sitter—
instantly.
Matched to their energy, personality, and needs.
BuddyBig energy 
His personLong-walk pro Same pace · Golden experience · Close to home
✦ How Matching Works
What makes them right for your dog?
Tell us about your dog’s energy, behavior, and routine. Tails narrows vetted caregivers to the people who fit.
- ✓Big energyNeeds real exercise
- ✓Strong pullerConfident handling
- ✓Lincoln ParkClose to home
48vetted caregivers
3 caregivers matched
3 caregivers match Buddy’s needs.
✦ See The Proof
You’ll know where they walked.
What they ate. When they pooped.
Meet first, track walks, and get care reports.
✓ Meet before you book
See how your dog responds. Book only when you're sure.
✓ 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
Background checks are just the start.
We interview every provider to verify hands-on care skills
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.
Free Meet-Up vs. Booking Sight Unseen
See how your matched provider bonds with your dog during a free meet-up before you book.
✦ Our Services
What does your dog need?
Boarding
Cozy overnight care with photo updates. Your pet gets belly rubs, treats, and lots of love!
Learn more ↗
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 ↗★★★★★ Verified booking reviews
What Chicago’s most obsessive dog moms & dads are saying
“Lauren gives Sneezer a comfortable, friendly, safe place. We always feel good booking her and head out worry-free.”
— Morgan V, West Loop
“Bruno loves Ariel. She makes time when we need help quickly, and it’s obvious she cares about animals.”
— Patty F, Oak Park
“Martin confidently handles my strong, energetic Lab. Emmy came back happy and well-exercised.”
— Aly M, Uptown
✦ 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.
Tell us about your dog
Breed, energy level, temperament, special needs — the stuff that actually matters for finding the right fit.
See your matches and why
We show you providers matched to your dog's specific needs — with the reasons behind each match.
Book a free meet & greet
Watch your dog meet their caregiver in person. Only pay when you're ready to book.
Your dog’s person could be two minutes away. Build their profile and meet the shortlist.
See My Dog's Match✦ Now Available on iOS & Android
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
Walk complete2.4 miles · 46 min
✦ The details
Frequently asked questions
Couldn’t find what you were looking for? We’re here to help! Send us an email.
How does Tails vet pet care providers?+
Our 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.
What makes Tails different from Rover?+
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.
How does your matching process work?+
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.
What if my pet doesn't like the provider during the meet & greet?+
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.
What's included in the daily reports?+
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.
How much can I earn as a Tails provider?+
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.
What insurance coverage do you provide?+
Booking insurance is coming soon. We can also help pet parents buy pet care insurance and pet care providers buy pet sitter insurance.