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Robbie said he could board her and he did amazing.Dog Sitters in Chicago, IL are rated 4.8 out of 5 stars based on 228 reviews of the 514 listed dog sitters. 514 affordable dog sitters in Chicago, IL. Average rate: $15.82/hr. Search the world's largest care website for free! The pay depends on the type of services you offer, your experience and your location. For dog walking, the average price for one dog is £12 per walk. For dog sitting, average prices hover around £20 per night. At Holidog, you get to set your own dog sitter rates and are free to look up other dog sitters in your area to compare. Why members love TrustedHousesitters. Verified sitters. Feel safe and secure with referenced, reviewed, and verified sitters. Unlimited pet care. Pay once a year to arrange as many sits as you like. Expert veterinary advice. Relax knowing you or your sitter can call a free 24/7 Vet Advice Line. Help and support.4. Lovett’s Lovin Pet & Home Care. 5.0 (1 review) Pet Sitting. Dog Walkers. 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