Dog Walking Winnetka
Book a dog walker to give your dog a 30-minute walk around your neighborhood.
Over 16 pet parents in Winnetka have booked dog walking
Winnetka, Find top rated dog walking
Prices are estimates per walk. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Thank you Ella for walking our two pups while we traveled to Greece!!!We loved getting daily updates with photos while we were gone!!You were such a gift to us that we could travel with the comfort knowing they were so well cared for!!!🐶🐶💖💖”
“We have had a great experience with Jon! He was extremely responsive, reliable, and trustworthy. Jon was wonderful with our dog and took the time to understand his specific needs and personality. He was incredibly patient with him, which we really appreciated. We felt completely comfortable knowing our dog was in good hands. We would absolutely recommend Jon and will definitely use him again!”
About: Starting at a young age of 8, I've cared for animals of friends and family. Ranging in all ages of cats and dogs, I'm confident in administering medication if needed and not scared of any sort of clean up. Having just moved back to the Chicagoland area from NOLA, my schedule is flexible. I am available for drop in visits and dog walking! I like to bike when weather permits but have access to a car as well. I do not offer services at my home but would treat yours as my own. Of course, cleaning up after your fur bb(s), following specific directions, and making sure they are settled before leaving.
About: I’ve cared for dogs since our family fostered a neighbor’s pup when I was 8 years old. Since then, in my multi-dog household, I have successfully cared for, trained, and housebroken puppies as well as cared for senior dogs. I have extensive experience training and handling reactive and anxious dogs (medium & large breeds), including handling multiple at the same time. I’ve been relied on my neighbors, family, and friends to care for their beloved dogs and cats for many years. I am a warm and compassionate experienced pet owner who is used to caring for dogs of all sizes, ages, and temperaments. I currently do not work a 9-5 job, so I have lots of flexibility and time to spend caring for pets. I am available for dog walking as well as house sitting and pop-in playtime. ** Though I cannot board a pet in my own home, I am more than happy to spend lots of time with your pet to keep them company as well as playtime with my two dogs to keep them company if desired. I can provide a regular walk schedule on weekdays and weekends. I am available to house sit to keep your dog’s schedule and environment as consistent as needed. **
“I would highly recommend Kevin and we will be using him again. He is very responsible and extremely punctual. He was on time for every visit. He sent pictures and videos for every walk. He responded to every concern promptly when I texted him. My dog Patch liked Kevin so much he did not want him to leave.”
About: I've been caring for dogs since I was young, starting with my neighbor's Old English Sheepdog. Today, I'm the go-to sitter my sister relies on to care for her little fluffball, whether it's for an evening away or extended vacations. I'm comfortable providing consistent, attentive care for every pet -- and following your every instruction to make sure your pet stays happy and healthy while you're away. I currently work a flexible, non-traditional schedule that includes fantasy illustration projects and teaching art classes. This gives me built-in gaps during the day that I'd love to fill with dog care, whether that means walks, playtime, or multi-day companionship. Your dog's routine and well-being are my top priorities. I make sure that your dog gets the best care possible and will follow all instructions to the letter: setting phone alarms to ensure potty breaks and meals happen right on time, monitoring treats so your dog is neither over- nor under-indulged, and sticking closely to established sleep schedules. I'm equally respectful of your home, taking care to leave it as clean and orderly (or better) than when I arrived.
About: I look forward to playing with your cats and giving them all the tummy rubs. My cats love lazer. But I am open to all your fur baby needs I am currently in between jobs. I have open availability right now - Sunday through Saturday. I am open to drop in visits and over night visits for vacation-goers Setting up meet and greets to make sure its a good fit. I care for my own pets in my home by making sure they have their own space to wonder and explore without getting hurt.
About: I’ve been a dog walker/dog sitter for almost 10 years. I love all animals especially dogs and would love to help with any services you may need. I had a dog of my own for most of my childhood that sadly passed away of old age a few years ago so now I love to care for other’s furry families ☺️ I always had a love for animals and I’m currently enrolled online to become a veterinary tech and feel like I learn more and more everyday by being around other’s pets. I work from home and have my 8 year old son with me who loves animals as well. We’re really looking forward to hearing from you and working with you soon! Thank you 😊
“Tina just started walking my dog, and so far she’s great! She seems to really care about my pup, she’s very responsive and accommodating. I asked her last minute to change the time she walked my dog and Tina had no problem with it! I will continue to book with Tina in the future.”
About: I’ve been around dogs since I was a kid but a few years ago, I started to help my boyfriend in bathing, feeding, walking, and taking care of his dog. Since then, I have also started watching dogs for my friends and family members when they need assistance. I am currently available all day, any day to take care of pets as I work remotely and have flexibility in my day to day schedule. I would care for pets in my home by spending time with them, feeding them, walking them, and making sure that they have fun for the duration of their stay :)
The median cost per walk for dog walking in Winnetka is $20
Dog parents share their Rover experiences - Winnetka
We have had a great experience with Jon! He was extremely responsive, reliable, and trustworthy. Jon was wonderful with our dog and took the time to understand his specific needs and personality. He was incredibly patient with him, which we really appreciated. We felt completely comfortable knowing our dog was in good hands. We would absolutely recommend Jon and will definitely use him again!
Book with peace of mind
- Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
- Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
- 24/7 support from the Rover team–here to help if you ever need someone to talk to.
Why Choose Rover?
Cashless payments
Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
How to book dog walking
1. Search
Browse profiles of walkers near you who offer dog walking.
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit.
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform.
Popular requests for dog walking - Winnetka
Select a filter and find qualifying sitters offering dog walking.Sitters in Winnetka average 4 repeat dog walking clients
FAQs for Dog Walking - Winnetka
Frequently asked questions about Rover
The average cost of Dog Walking in Winnetka is $13 per walk as of November 2026. Most bookings cost between $0 and $28 per walk. On Rover, walkers set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.
As of November 2026, there are 12,165 sitters on Rover offering Dog Walking across Winnetka. Enter your ZIP code to see which available sitters are closest to your home.
Whether you want a solo or group walk depends on your dog's personality. Solo walks can be beneficial for dog parents with reactive dogs, puppies, or dogs who are anxious around unfamiliar animals. Many dog walkers on Rover offer private, one-on-one walking services.
Group walks are a good fit for social dogs who enjoy structured walks. If your dog prefers the energy of a group stroll, ask your dog walker about group walks in Winnetka. Since all dog walkers are local, they may have a neighborhood dog who is a good walking companion to yours.
For dog walking bookings, your dog walker can send a Rover Card with details about your dog’s walk. Rover Cards require at least one photo and may include a map of the walking route, the total walk time and distance, and any pee or poop breaks recorded by the walker.
The route map lets you review where your dog was walked in Winnetka after the booking. It is not live GPS tracking.
Have specific details you would like included? Message your dog walker in the app before the walk begins.
The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.
All bookings are backed by the Rover Guarantee, which provides up to $25,000 in eligible veterinary care reimbursement.
Every walker on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.
Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page.
Yes, you can find walkers who have experience with handling special pet needs in Winnetka. On Rover:
- 85% of walkers can help with special care needs
- 90% can help with giving oral medications or injections
- 95% can help with daily exercise
You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.
Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.
A Meet & Greet is a casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.
Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your walker interacts with your pet or the new environment.
During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your walker questions about their skills and expertise, and make sure the fit feels right for everyone. Meet & Greets are a great way to prepare your pet and walker for longer stays or first-time bookings. Read our tips for your first Meet & Greet.
walkers on Rover set their own cancellation policy, which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.
Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement walker.
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