The Best Dog Sitters in Chicago
Vetted, trusted dog sitters matched to your dog's unique needs. Overnight boarding, house sitting, day care & more across Chicago neighborhoods.
Why Chicago Dog Owners Choose Tails
Personally Vetted Sitters
Every sitter passes interviews, background checks, and reference verification before joining Tails.
Matched to Your Dog
We pair you with sitters based on your dog's personality, needs, and your preferences.
Multiple Care Options
Overnight boarding, house sitting, dog walking, day care—find the perfect fit for your schedule.
Daily Photo Updates
Stay connected with your dog through photos, videos, and messages from your sitter.
Find Your Perfect Dog Sitter in 4 Easy Steps
Booking trusted dog care in Chicago has never been simpler.
Tell us about your dog's personality, routine, and any special needs or preferences.
We'll recommend vetted Chicago sitters who are the best fit for your dog.
Meet your potential sitter and ensure it's the perfect match—no obligation.
Confirm your booking and enjoy peace of mind with daily updates.
Create Your Dog's Profile
Tell us about your dog's personality, routine, and any special needs or preferences.
Get Matched with Sitters
We'll recommend vetted Chicago sitters who are the best fit for your dog.
Free Meet & Greet
Meet your potential sitter and ensure it's the perfect match—no obligation.
Book with Confidence
Confirm your booking and enjoy peace of mind with daily updates.
Find the Right Dog Sitting Service for You
Whether you need overnight care, daily visits, or regular walks—our Chicago sitters have you covered.
Overnight Boarding
Your dog stays in a sitter's home. Perfect for vacations and work trips when you need full-time care.
House Sitting
A sitter stays in YOUR home with your dog. Ideal for pets who thrive in familiar surroundings.
Doggy Day Care
Daytime care while you work. Socialization, exercise, and enrichment in a home environment.
Drop-In Visits
Scheduled visits for feeding, potty breaks, and playtime. Great for independent dogs.
Dog Walking
GPS-tracked walks with photo updates. Keep your dog exercised and happy during the day.
Special Needs Care
Experienced sitters for seniors, puppies, dogs with medical needs, or anxiety support.
Overnight Boarding
Your dog stays in a sitter's home. Perfect for vacations and work trips when you need full-time care.
House Sitting
A sitter stays in YOUR home with your dog. Ideal for pets who thrive in familiar surroundings.
Doggy Day Care
Daytime care while you work. Socialization, exercise, and enrichment in a home environment.
Drop-In Visits
Scheduled visits for feeding, potty breaks, and playtime. Great for independent dogs.
Dog Walking
GPS-tracked walks with photo updates. Keep your dog exercised and happy during the day.
Special Needs Care
Experienced sitters for seniors, puppies, dogs with medical needs, or anxiety support.
Chicago's Most Trusted Dog Sitters
Your dog's safety is our top priority. Every Tails sitter goes through our rigorous vetting process.
Comprehensive Background Checks
Every sitter is screened with identity verification and criminal background checks.
Personal Interviews
We meet every sitter virtually to assess experience, knowledge, and passion for pet care.
Reference Verification
We verify references from previous pet care experience.
Ongoing Support
Our team provides 24/7 support for any questions or emergencies.
Comprehensive Background Checks
Every sitter is screened with identity verification and criminal background checks.
Personal Interviews
We meet every sitter virtually to assess experience, knowledge, and passion for pet care.
Reference Verification
We verify references from previous pet care experience.
Ongoing Support
Our team provides 24/7 support for any questions or emergencies.
What Makes Tails Different
Quality Over Quantity
We're selective about our sitters—only the best make it through our vetting process.
Personalized Matching
We don't just list sitters—we match you based on your dog's unique needs.
Real Homes, Not Facilities
Your dog gets one-on-one attention in a comfortable home environment.
Chicago-Focused
Our sitters know Chicago neighborhoods and can recommend the best dog parks and walking routes.
Transparent Communication
Daily updates, photos, and easy messaging keep you connected to your dog.
Dog Sitting Questions? We've Got Answers
Find Dog Sitters in Your Chicago Neighborhood
Trusted sitters available throughout the city:
What Chicago Dog Owners Say
"Finally found a sitter I can trust! The vetting process gave me confidence, and Maya adores her sitter."
"The matching process was spot-on. Our anxious rescue needed a calm, patient sitter and that's exactly what we got."
"We've tried other apps, but Tails is different. The sitters are higher quality and the updates are amazing."
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
