Tails

Tails offers in-home dog boarding in Chicago, placing dogs with vetted local sitters for overnight stays and daycare instead of a traditional kennel. The service is based at 680 North Lake Shore Drive and matches each dog to a caregiver who fits its energy, behavior, and routine. Stays are cage-free, and bookings are made online.

What services does Tails offer?

Tails covers overnight boarding in vetted Chicago homes, doggy daycare, and walks. Each match starts from a profile of the dog. That means a strong, high-energy dog and a nervous senior should end up with different sitters.

• In-home overnight boarding in vetted homes
• Doggy daycare
• GPS-tracked dog walks
• Medication administration
• Daily photo updates and care reports

How are the sitters vetted?

Every sitter goes through ID verification, a background check, and an in-person interview. The interviews happen face to face, so the screening goes beyond paperwork. If a sitter cancels, Tails arranges backup coverage so owners aren't left scrambling before a trip.

Is it a good fit for dogs with special needs?

Tails provides specialized care for senior dogs, puppies, and anxious or reactive dogs. Sitters can give medication during a stay. Owners who are unsure about a match can book a free meet and greet first and see how their dog responds before committing.

Practical details

Vaccinations are required for every dog. Booking happens online, and the team can be reached at (312) 945-6761 or welcome@trytails.com. During a stay, owners receive daily photo updates and care reports, and walks are GPS-tracked so the route is on record. For owners who prefer a home setting and want some say in who looks after their dog, the matching approach is the main thing that sets Tails apart from a standard boarding facility.