Dog Walking Winnetka
Book a dog walker to give your dog a 30-minute walk around your neighborhood.
Over 18 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.
“Five stars and two paws up! Isa has an eye for detail, professional demeanor, and is easy to communicate with. She’s super responsible with my pup and I highly recommend her :-)”
“Stephen is great with our silly, high energy dog Roxy (doberman). We always feel comfortable she is in good hands under their care and she is always happy (based on the fun photo update we get). I would highly recommend their services”
“Amy was wonderful! She had great communication and was very flexible, which we really appreciated. Our dog Brady can be very nervous around new people, and Amy was so patient, respected his boundaries, and followed our instructions without pushing him. We felt very comfortable having her work with him and are so happy we connected with her. We’ll definitely be using Amy for future walks and highly recommend her!”
About: I have always been a natural with animals! I grew up with cats and dogs. My Dad has 5 cats and 3 dogs. I love them like they are my own. I am a nanny and I have some part time hours that I would love to fill. Spending time with animals would be a joy and a dream! I am able to follow any directions needed from the pet parent. I am happy to make sure I follow what is needed to provide care for your pet.
“Jenny was amazing with Shortcake. She took my chunk out on walks for me twice a day while I was away on a business trip. I love the photo updates and could tell that shortcake was really enjoying her time. I came hope to a very happy and well adjusted dog. I highly recommend Jenny!”
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. **
About: We treat all pets as family. We are home all day with our pets.There is a nice yard for them to play in and run.We also take them for long walks during the day.We enjoy dog sitting very much.We allow them on furniture and have lots of cozy time.What ever your pets schedule is we follow.Your pet will be well taken care of at all times.We can promise you that your pets will come home to you happy and healthy.Our goal is to assure your pet has quality care and to make sure our home is a happy home for your pet while you are away.We also do send you Photos during thier stay and updates daily.We want you to be able to go away relaxe enjoy and no your pets are happy and having fun and safe .
About: Enthusiastic and engergetic dog sitter. I love dogs. I love taking them to dog parks and on long walks in the forest preserve by my house. I've had dogs my whole life and always have taken great care of them to make sure they have a happy and fulfilled life. My most recent dog is a Collie named Buehrle with lots of energy. He loves to go for runs in fields and play with other dogs at the dog beach.
“Diana was prompt, responsive and reliable! She was great to work with and I felt so much relief leaving my pets in good hands while I was away. Thank you Diana! Will absolutely rebook soon”
About: Lifelong dog owner and experienced cat caregiver. Proud dog mom to my rescue, Poncho. I’ll provide loving, dependable care, updates, and plenty of attention every visit. My schedule is currently more flexible than usual since my recent work contract ended, which allows me to dedicate plenty of time to pet care. I’m available for walks, drop-in visits, and pet sitting throughout the week and can often accommodate last-minute requests. Caring for animals is something I genuinely enjoy, and I love being able to provide dependable, attentive care for pets while giving their owners peace of mind. Your pet’s safety, comfort, and routine always come first. I carefully follow all care instructions, including feeding schedules, medications, exercise needs, and any special requests. I’ll treat your home with the same respect I would my own and provide regular photo and message updates so you always know how your pet is doing. Although my senior dog passed away in January and I don’t currently have pets at home, I’ve volunteered with a local cat shelter for the past four years. That experience has strengthened my skills caring for animals with different personalities, needs, and comfort levels. Whether your pet is energetic, shy, or senior, I’ll provide patient, loving, and reliable care.
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 on Rover is $14 per walk as of October 2026. Most bookings cost between $0 and $28 per walk. 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 October 2026, there are 12,173 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 your 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 , 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 , 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 .
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 .
walkers on Rover set their own , 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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