Imagine this. You live in Lakeview. You found a dog walker online, good reviews, reasonable price, seemed fine. You handed over your keys, trusted the process, and headed to work.
That afternoon you get a call. Your dog was involved in an incident on the walk. Another dog lunged, there was a scuffle, and your dog came home shaken. The walker didn't know how to de-escalate. There was no incident report. No insurance claim to file. When you looked closer, you realized the person walking your dog wasn't licensed to operate as a business in the City of Chicago. They were just someone with a profile and a phone.
You weren't asking the wrong questions. You just didn't know which questions to ask.
This story happens more than people realize. Roughly 4.5 million dog bites occur in the United States every year, and while the majority are minor, hundreds of thousands of people require emergency care. Chicago consistently ranks among the top cities in the country for dog-related incidents. And when something goes wrong on a walk, the difference between a licensed, insured walker and an unlicensed one is the difference between accountability and a dead end.
Here's something worth saying before we go any further.
All dogs are good dogs. But dogs have bad days, just like people do. A dog that has never shown aggression in its entire life can have a moment. Maybe they're in the early stages of something medical and their owner doesn't know yet. Pain can do that, it can make a gentle dog suddenly unpredictable in a way that surprises everyone, including the dog's own family. It doesn't make the dog bad. It makes the situation complex.
That's exactly why the person on the other end of the leash matters so much. A trained, experienced, licensed walker knows how to read body language. They know when to cross the street, when to shorten the leash, when to cut the walk short and come home. They carry extra equipment. They know what to do if something happens, and they have the insurance to back it up if it does.
An unprepared walker doesn't. And by the time you find out, it's too late.
Questions to ask before handing over your keys
Are you licensed to operate in the City of Chicago?
Dog walking is a business. In Chicago, operating a business requires a city license. Ask to see it. A professional will have no problem showing you.
Are you insured, bonded, and do you carry animal bailee coverage?
These three sound like the same thing but they cover very different situations.
Think of it this way. General liability covers the walker accidentally breaking something in your home while picking up your dog. Bonding covers you if something goes missing from your home — a key gets copied, something walks out the door. Animal bailee coverage is the one most people don't know about, and it's the most important one for your dog specifically. It covers your pet if they're injured, lost, or die while in someone else's care.
Imagine your walker takes your dog out on a Tuesday afternoon. Another dog charges and there's a scuffle. Your dog needs emergency vet care, stitches, x-rays, overnight observation. That bill can easily run into the thousands. Animal bailee coverage is what pays for it when the incident happened on someone else's watch. Without it you're filing the claim yourself and hoping for the best.
A professional carries all three. If someone only mentions "insurance" without being able to explain what it actually covers, keep asking.
What happens if my dog is injured on a walk?
A prepared walker has a clear answer. They have a vet authorization process, an emergency contact protocol, and they know which clinic they'd take your dog to. Vague answers here are a red flag.
Do you walk multiple dogs from different households at the same time?
Pack walks sound efficient. But mixing dogs from different households on a single walk increases unpredictability significantly. Know what you're agreeing to.
What's your cancellation and refund policy, and do I pay before or after the walk?
This tells you a lot about how seriously someone runs their operation. A professional has clear, written policies. A hobbyist figures it out as they go.
Can I see a sample walk report?
After every walk you should receive a report, what happened, how your dog did, photos. If they've never done one, that's worth knowing upfront.
You love your dog. The person walking them should operate like it.