The Best Pet Sitters in Chicago
Trusted, vetted pet sitters who specialize in dogs. Overnight boarding, house sitting, day care & more across Chicago neighborhoods.
Why Chicago Pet Owners Trust Tails
Thoroughly Vetted Sitters
Every pet sitter passes interviews, background checks, and reference verification.
Personalized Matching
We match you with sitters based on your pet's personality, needs, and your preferences.
Flexible Care Options
Overnight boarding, house sitting, dog walking, day care—choose what works for you.
Stay Connected
Get daily photo updates and messages from your pet sitter while you're away.
Find Your Ideal Pet Sitter in Minutes
Booking trusted pet care in Chicago is quick and easy with Tails.
Tell us about your dog's personality, routine, and any special needs.
We'll recommend vetted Chicago pet sitters who are perfect for your dog.
Meet your potential sitter to ensure it's the right fit—no obligation.
Confirm your booking and enjoy peace of mind with regular updates.
Create Your Pet Profile
Tell us about your dog's personality, routine, and any special needs.
Get Matched with Sitters
We'll recommend vetted Chicago pet sitters who are perfect for your dog.
Free Meet & Greet
Meet your potential sitter to ensure it's the right fit—no obligation.
Book with Confidence
Confirm your booking and enjoy peace of mind with regular updates.
Choose the Right Care for Your Pet
From overnight stays to daily walks—find the perfect pet sitting solution.
Overnight Pet Boarding
Your dog stays in a sitter's home with full-time care. Great for vacations and travel.
In-Home Pet Sitting
A sitter stays at YOUR home. Perfect for pets who prefer their own environment.
Doggy Day Care
Daytime care while you work. Play, exercise, and socialization in a home setting.
Pet Drop-In Visits
Scheduled visits for feeding, potty breaks, and companionship.
Dog Walking
GPS-tracked walks with updates. Keep your dog active and healthy.
Special Needs Pet Care
Experienced sitters for seniors, puppies, medication, and anxiety support.
Overnight Pet Boarding
Your dog stays in a sitter's home with full-time care. Great for vacations and travel.
In-Home Pet Sitting
A sitter stays at YOUR home. Perfect for pets who prefer their own environment.
Doggy Day Care
Daytime care while you work. Play, exercise, and socialization in a home setting.
Pet Drop-In Visits
Scheduled visits for feeding, potty breaks, and companionship.
Dog Walking
GPS-tracked walks with updates. Keep your dog active and healthy.
Special Needs Pet Care
Experienced sitters for seniors, puppies, medication, and anxiety support.
Chicago's Most Reliable Pet Sitters
Your pet's safety comes first. Every Tails sitter is carefully vetted.
Background Screening
Identity verification and criminal background checks for every sitter.
In-Person Interviews
We assess every sitter's experience, knowledge, and genuine love for pets.
Reference Checks
We verify pet care experience through previous references.
24/7 Support
Our team is available around the clock for questions or emergencies.
Background Screening
Identity verification and criminal background checks for every sitter.
In-Person Interviews
We assess every sitter's experience, knowledge, and genuine love for pets.
Reference Checks
We verify pet care experience through previous references.
24/7 Support
Our team is available around the clock for questions or emergencies.
The Tails Difference
Selective Vetting
Only the best pet sitters make it through our rigorous screening process.
Smart Matching
We pair you with sitters based on your pet's specific needs and personality.
Home Environment
Your pet gets individual attention in a real home, not a crowded facility.
Local Chicago Expertise
Our sitters know the best dog parks, vet clinics, and walking routes in your area.
Clear Communication
Photo updates, easy messaging, and transparent booking keep you informed.
Pet Sitting Questions Answered
Pet Sitters Across Chicago
Find trusted care in your neighborhood:
Happy Pet Owners in Chicago
"Found an amazing pet sitter through Tails! The vetting process was thorough and our dog loves her."
"The matching was perfect for our anxious pup. Patient, calm sitter who followed our routine exactly."
"Best pet sitting service we've used. Quality sitters, great communication, and my dog is always happy."
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
