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.
“Bill is a reliable dog walker. He was great with our dog, Bella. He was flexible when adding extra walks last minute. He is also very responsive. I highly recommend his services to others.”
“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!!!🐶🐶💖💖”
“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 :-)”
About: I give a lot of attention to dogs and can walk them on extra long walks if needed. For puppies, if they need to play with other dogs, I have my own senior dog (shihtzu-terrier mix) they can play with. I’m currently working part-time on nights so I can walk and feed your dogs as needed. I’m very flexible with your schedule and can be available when needed. I can offer the dog lots of attention, TLC, extra long walks, feeding, and/or any medicine needed to take orally. I also have a car and can pick up/drop off the dog when needed.
“Andrew was able to come through when our usual sitter had a time conflict last-minute. He was very communicative, easy-going, and professional. When he noticed our dog was really enjoying the walk, he took him out for a even longer walk than was expected, and our dog was definitely feeling the love! Highly recommend Andrew.”
“Times did a wonderful job walking our two dogs mostly while we were at work. She was on time, made sure our home was secure and the dogs were well cared for. Rudy and Dasher both said they loved spending time with her! We will definitely use her again!”
About: I have always had at least 2 animals in my house, which helped me learn how to be responsible at a young age. Then when I was older, I would help me neighbors and other friends when they went out of town, so I have been taking care of dogs/cats for a while! I am in college right now, so I will have some spare time to stop by/walk dogs. My class schedule is spread out nicely, so I will have more than enough time and flexibility. I will help your pets in your home, and try to follow their normal routine. I can crate, feed, walk, play, anything you could ever need!
“Donna and Stephen have truly been lifesavers over the past few weeks. They are incredibly timely and dependable, and they are always willing to help when they can. I also LOVE receiving multiple photos of my pup enjoying the walk so I know how happy he is to be out with them. Would strongly recommend this wonderful team to walk your furry friend!”
“Anna is amazing! She has been walking our pup every day for the past few months. Anna not only walks Charlie but actually spends time playing with him and training him - she even taught him the paw command! Anna sends very detailed reports and lots of cute pictures after every walk. Being first time puppy owners we feel so lucky to have Anna looking after our pup!”
“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”
“Alexis is awesome! She clearly loves and is comfortable with dogs and connected with my owner-attached dog straight away. She is super friendly and easy to work with. She also is very responsible--she was on time, listened to and executed my exercise requirements for my dog. I will definitely use her again!”
About: I have taken care of dogs since I was 10 years old! I have had my own cockapoo since 2014 and have also routinely taken care of dogs of friends and family since then. I have experience walking neighborhood dogs of mostly small to medium sizes. I love spending time with my own dog and miss having him around while I am away at school. Dogs bring me a lot of joy, and I love getting to know the unique personality of every dog that I take care of! I am very excited to spend time with your dog :) I am currently a part-time student at Northwestern, so my schedule is very flexible! I am generally available Sunday through Wednesday as well as Saturday anytime after 11am. I am happy to walk your dog for however long is necessary as well as doing check-ins during the day while you are away!
About: I’ve been around dogs my whole life and have spent the past few years helping care for all sorts of fur babies ! I’ve helped with dog walks, drop-ins, pet sitting, and spending time with dogs of all breeds, sizes, and personalities. I’m obsessed with all fur babies and I’m very comfortable handling all sizes and all breeds! We don’t discriminate😆 I am super accommodating! I love going on walks and how cute to have a little companion to get my steps in with! Over the years I’ve learned how important patience, consistency, and love are when it comes to caring for animals. I always make sure every fur baby feels safe, comfortable, and well cared for while their owners are away. Spending time with animals is something I genuinely enjoy, and I treat every single one like they’re my own.
About: I have experience working with cats and dogs. My family adopted a cat a few years ago and she quickly became part of the family. I have experience walking my neighbors dogs and know how to tame a dog if need be. Working with cats and dogs is a passion of mine as each has their own unique personality that is discovered over time. I am a college student at the Royal Conservatory of Music Glenn Gould School. I am available most afternoons Monday to Saturday, except for Sunday. I have a large fenced backyard that is safe for dogs to soak up the sun while having fun exploring, running around, and playing games
The median cost per walk for dog walking in Winnetka is $20
Dog parents share their Rover experiences - Winnetka
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?
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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.
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We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
How Rover works
1. Search
Browse profiles of sitters near you who offer dog walking
2. Meet & Greet
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 near you
Select a filter and find qualifying Winnetka sitters!Sitters in Winnetka average 4 repeat dog walking clients
FAQs for Dog Walking - Winnetka
Frequently asked questions about Rover
The average cost for Dog Walking in Winnetka on Rover is $12.84 per walk (as of June 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of Dog Walking easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Dog Walking. For more information on service fees, click here .
As of June 2026, there are 12,522 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 services, you can request a report card update with specifics about your dog’s walk. Report cards require photos and can include a map of the walking route , total walk time, poop and pee breaks, and distance traveled, so you know exactly where your dog has been walking in Winnetka.
Got specific details you'd like the dog walker to include? Message them in the app before your dog’s 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:
- 91% of walkers can help with special care needs
- 95% can help with giving oral medications or injections
- 97% 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 short introductory meeting between you, your dog, and a walker. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your walker 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. Most pet parents and walkers on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.
Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.
Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement walker.
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