Safe & Loving Dog Boarding in Chicago Your Pet Will Adore
Premium overnight care in a real home with a personally vetted provider who'll treat your dog like family.
Peace of Mind for Pet Parents in Chicago
Real Homes, Not Kennels
A comfortable, less stressful stay in a real Chicago home.
Vetted & Trained Sitters
Every sitter is interviewed, background-checked, and trained.
Personalized Matching
We connect you with sitters suited to your dog's specific needs.
Daily Photo Updates
Stay connected with photos and messages from your sitter.
Your Simple Path to Worry-Free Boarding
Booking safe, personalized dog boarding in Chicago is easy with Tails.
Create a detailed profile covering personality, routine, medical needs.
Based on your profile, we'll suggest vetted, local sitters.
Schedule a no-obligation meeting to ensure a perfect match.
Confirm your booking easily and receive loving care with updates.
Tell Us About Your Pup
Create a detailed profile covering personality, routine, medical needs.
Get Matched with Chicago Sitters
Based on your profile, we'll suggest vetted, local sitters.
Free Meet & Greet
Schedule a no-obligation meeting to ensure a perfect match.
Peace of Mind
Confirm your booking easily and receive loving care with 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 Dog's Safety is Our Top Priority in Chicago
We go above and beyond to ensure every stay booked through Tails is safe and secure.
Rigorous Sitter Vetting
Includes ID verification, background checks, and interviews.
Home Safety Checks
Home photos by Tails so you can be sure about your pet's home away from home.
Emergency Support
Our dedicated team is available just in case.
Secure Platform
Safe messaging and payment processing.
Rigorous Sitter Vetting
Includes ID verification, background checks, and interviews.
Home Safety Checks
Home photos by Tails so you can be sure about your pet's home away from home.
Emergency Support
Our dedicated team is available just in case.
Secure Platform
Safe messaging and payment processing.
A True Home Away From Home
One-on-One Attention
Sitters typically care for only one or two dogs at a time.
Stress-Free Environment
Avoid the noise and anxiety of traditional kennels.
Routine Consistency
Sitters follow your dog's normal feeding, exercise schedule, and medication schedules.
Daily Exercise
Regular walks and playtime tailored to your dog's energy level.
Real-Time Updates
Receive photos, videos, and messages directly from your sitter.
Your Chicago Dog Boarding Questions Answered
Convenient Dog Boarding Across Chicago
Find trusted sitters in your neighborhood, including:
What Chicago Dog Owners Are Saying
"Leaving Leo used to be so stressful... Maria through Tails was a game-changer!"
"The Meet & Greet was key... The boarding stay was flawless."
"The vetting process gave us confidence... sitter was amazing, updates were fantastic."
Ready for Worry-Free Travel?
Find a trusted, vetted dog boarding sitter in Chicago today.
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.