Forget the kennel! Board your dog in a real home with DogVacay.com. We have hundreds of vetted and insured dog lovers in and near Chicago, Illinois ready to watch your dog like a member of their family. Simply browse dog sitters (aka Hosts) in Chicago, schedule and book online. Rates start at $15/night and all home dog boarding and dog sitting reservations include complimentary insurance, 24/7 customer support and daily photo updates.