Finding the best pet sitters in Chicago means going beyond star ratings. The sitters worth trusting with your dog have in-person vetting, breed-specific experience, and real accountability—not just an app profile.
What Sets the Best Chicago Sitters Apart
- In-person vetting: Background check plus a face-to-face interview—not just an online application
- Breed experience: Handling reactive dogs, high-energy breeds, seniors, or puppies with special needs
- Pet first aid certification: Trained to handle emergencies before the vet visit
- Free meet-and-greet: Lets your dog meet the sitter before you commit
- Daily updates: Photos, GPS tracking, and detailed reports on walks, meals, and mood
- Low client-to-sitter ratio: Top sitters limit their roster to give each dog real attention
How to Vet a Chicago Dog Sitter
Start with a phone or video call to discuss your dog's routine, quirks, and medical needs. Ask about their experience with your breed, how they handle emergencies, and what a typical day looks like with your dog in their care.
During the meet-and-greet, watch how your dog reacts—and whether the sitter follows your instructions without prompting. The best sitters in Lincoln Park, Lakeview, Bucktown, and Wicker Park fill up fast during holidays and summer, so book early.
What to Expect to Pay
Quality dog sitting in Chicago runs $50–$100/day depending on neighborhood and services. Gold Coast and River North tend toward the higher end. Most top sitters offer discounts for multi-day bookings. Read our sitting vs boarding comparison to decide which option fits your dog, or browse Chicago sitters on Tails.