Professional Dog House Sitting in Chicago

Keep your dog happy and secure with overnight care from trusted, vetted Chicago house sitters.

Find Your Sitter
Vetted Sitters
Overnight Care
Daily Updates
Curated by Pawel Kaczmarek, Founder & CEO
Updated:
Founded 2024
Dog relaxing at home with a Tails house sitter in Chicago

Why Choose In-Home House Sitting?

Comfort of Home

Minimize stress by keeping your dog in their familiar environment and routine.

Personalized Attention

Your dog receives one-on-one care and companionship.

Home Security

Enjoy peace of mind knowing your home is occupied and cared for.

Maintained Routine

Feeding, walks, and medication schedules stay consistent.

How It Works

Arranging House Sitting is Easy

Find the perfect sitter to care for your dog and home in Chicago.

Create a profile for your pet and outline home care instructions.

Illustration for Detail Your Needs

Review profiles of vetted Chicago sitters available for your dates.

Illustration for Match with House Sitters

Ensure compatibility and walk the sitter through your home and pet's routine.

Illustration for Meet & Greet + Home Tour

Confirm your booking and receive updates while you're away.

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Find Your Sitter
Specialized Care

Care Tailored to Your Dog's Needs

Our experienced pet sitters can accommodate special requirements so your dog receives the right care while you're away.

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.

Find Your Sitter
Trust & Safety

Reliable Care for Your Pet & Home

We ensure sitters are thoroughly vetted and respect your home as their own.

Rigorous Sitter Vetting

Extensive checks including background screening and interviews.

Respect for Your Home

Clear guidelines and expectations set for sitters staying in your home.

Emergency Support

Our dedicated team provides backup support for pets and sitters.

Secure Platform

Safe messaging and payment processing.

Our Commitment to Safety →

Seamless Care While You're Away

Stress-Free for Your Pet

Your dog stays comfortable with their own bed, toys, and familiar smells.

Continuous Companionship

Overnight presence minimizes loneliness and anxiety for your dog.

Updates From Home

Receive regular photos and messages about your pet's well-being.

Added Home Security

An occupied home deters potential issues while you're gone.

Dog sleeping peacefully at home while being house-sat by a Tails sitter

House Sitting Questions Answered

Every provider completes ID verification, background checks, and a live interview. You can review profiles, experience, and ratings before booking.

Yes. Tails is a Chicago-based pet care marketplace with rigorous vetting, including background checks and live interviews. Our Trust & Safety team is available for support, and we can help pet parents and providers find the right insurance for their needs.

Insurance is handled individually by providers. We encourage all providers to carry liability insurance and can help both pet parents and providers find the right coverage for their needs.

Tails serves neighborhoods across Chicago including Lincoln Park, Wicker Park, Lakeview, Logan Square, Bucktown, Old Town, Gold Coast, River North, West Loop, Hyde Park, and many more. Check the Tails app for availability in your specific area.

For regular services, 24-48 hours is usually sufficient. For holidays or peak times, book 1-2 weeks ahead. Last-minute bookings may be available depending on provider schedules.

All payments are handled securely through the Tails app via credit card or debit card. You'll see the total before confirming, and payment processes after service completion.

You'll receive photos and notes in the Tails app after each service. For walks, you'll also see GPS route tracking when available. Want to test it on your own walks? Try our free GPS dog walk tracker.

You can modify or cancel in the app. Policies vary by provider and timing, so you'll see the exact policy before confirming.

Pricing varies by sitter, number of pets, and length of stay. You’ll see exact rates before booking.

They stay in your home, providing feeding, walks, playtime, medication, and maintaining your pet’s routine.

Yes. House sitting includes overnight stays, with short breaks for personal errands similar to your own routine.

Absolutely, if it’s part of your routine and safe for your dog. Sitters may visit Wiggly Field (Noethling Park), Montrose Dog Beach, or Horner Park DFA when appropriate.

Sitters follow your vet instructions and emergency contacts. Our support team can assist 24/7.

Yes, light house tasks are often included. Discuss details during the Meet & Greet.

House Sitting Available Across Chicago

Find trusted house sitters in your neighborhood, including:

Wicker Park Lincoln Park Logan Square Lakeview West Loop Gold Coast River North South Loop Bucktown Roscoe Village Old Town Lincoln Square Andersonville North Center Edgewater Uptown Ravenswood Albany Park Rogers Park Wrigleyville Portage Park Jefferson Park Avondale Irving Park Old Irving Park Ukrainian Village Noble Square Hyde Park Pilsen West Town Humboldt Park Hermosa River West Dunning Belmont Cragin The Loop Streeterville Greektown DePaul West Ridge North Park Forest Glen Norwood Park Bridgeport East Village Little Village University Village Chinatown Bronzeville Woodlawn South Shore Kenwood Washington Park
Map of Chicago highlighting Tails service areas

House Sitting Guides & Resources

What Chicago Pet Parents Say About Our House Sitters

"Leaving town is so much easier knowing Max is happy at home with his Tails sitter."

Olivia R.

Owner of Max • Chicago

"Our house sitter was amazing! Professional, communicative, and took great care of our dog and home."

Brian K.

Owner of Lucy • Chicago

"Complete peace of mind. Received daily updates and came back to a happy dog and tidy house."

Fatima A.

Owner of Charlie • Chicago

Now Available on iOS

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

Download on the App Store
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