Convenient Dog Drop-In Visits in Chicago
Reliable check-ins for potty breaks, feeding, medication, and playtime while you're away. Provided by vetted, caring Chicago sitters.
Benefits of Tails Drop-In Visits
Peace of Mind Check-Ins
Know your dog is okay with timely visits for potty, food, or company.
Maintain Routine
Keep your dog's feeding and medication schedule consistent.
Essential Potty Breaks
Prevent accidents and keep your dog comfortable during the day.
Medication Administration
Experienced sitters can administer medication as needed.
Booking Drop-In Visits Made Simple
Scheduling reliable dog check-ins in Chicago is quick and easy.
Include feeding instructions, medication needs, and visit routines.
We'll connect you with vetted Chicago sitters available for drop-ins.
Meet the sitter, discuss routines, and handle key exchange details.
Book single or recurring visits online and receive timely updates.
Create Your Pet Profile
Include feeding instructions, medication needs, and visit routines.
Match with Local Sitters
We'll connect you with vetted Chicago sitters available for drop-ins.
Free Meet & Greet
Meet the sitter, discuss routines, and handle key exchange details.
Schedule Visits Easily
Book single or recurring visits online and receive timely 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.
Secure and Reliable Visits, Every Time
Your pet's safety and your home's security are paramount for every visit.
Thorough Sitter Vetting
ID verification, background checks, interviews ensure trustworthy sitters.
Secure Key Handling
Protocols for safe key management or lockbox usage.
Emergency Support
Our team is ready to assist you or your sitter if needed during a visit.
Secure Platform
Safe messaging and payment processing.
Thorough Sitter Vetting
ID verification, background checks, interviews ensure trustworthy sitters.
Secure Key Handling
Protocols for safe key management or lockbox usage.
Emergency Support
Our team is ready to assist you or your sitter if needed during a visit.
Secure Platform
Safe messaging and payment processing.
Customized Care During Every Visit
Personalized Visit Tasks
Feeding, water refresh, potty breaks, playtime, medication - tailored to your needs.
Reliable & Timely Service
Sitters arrive within the scheduled window for consistency.
Photo & Note Updates
Receive confirmation and a quick update after each completed visit.
Easy Online Scheduling
Book and manage recurring or one-off visits through our platform.
Drop-In Visit Questions Answered
Drop-In Visits Available Across Chicago
Find trusted sitters for check-ins in your neighborhood, including:
What Chicago Pet Parents Say About Our Visits
"Tails drop-in visits are perfect for my long workdays. I know Rex gets his potty break!"
"So convenient and reliable for feeding my cat while I'm away for a day or two."
"Our sitter is wonderful and always sends a quick photo. Total peace of mind."
Ensure Your Pet is Happy & Safe at Home
Join the waitlist for reliable, vetted drop-in visits in Chicago.
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.