Dog Walking Kenwood

Book a dog walker to give your dog a 30-minute walk around your neighborhood.

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Over 108
pet parents in Kenwood have booked dog walking

Kenwood, 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.

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Sitter Profile Image: Tamara J.
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Tamara J.
Star Sitter
from
$25
per walk
4.9 out of 5 stars
274 reviews
98 repeat clients
16 years of experience
Grand Boulevard, Chicago, IL, 60653

Twix loves her so much! He knows her car at this point and is jumping for us to let him go with his friend. She is so amazing withy doodle who isn’t the easiest to walk cause he is a puller and she does perfect with him. I have also used her for boarding and day care and I know when he is with her he is so happy and well taken care of ♥️

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Rania A.
Sitter Profile Image: artiss m.
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artiss m.
Star Sitter
from
$17
per walk
5.0 out of 5 stars
13 reviews
5 repeat clients
20 years of experience
Chicago, IL, 60615

Artiss has walked my pup multiple times, and he has always been happy to see her! She has done a great job managing his high energy level, sent wonderful photo updates, and always made sure he went to the bathroom.

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Sourav H.
Sitter Profile Image: Manuela G.
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Manuela G.
from
$23
per walk
5.0 out of 5 stars
28 reviews
8 repeat clients
20 years of experience
Woodlawn, Chicago, IL, 60637

Manuela is great with my dog, very reliable and easy to communicate with. It makes my workday less stressful to work with her and i appreciate her a lot.

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Jennifer D.
Sitter Profile Image: Victoria G.
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Victoria G.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
34 reviews
6 repeat clients
30 years of experience
Hyde Park, Chicago, IL, 60637

Victoria did a wonderful job with our Australian Shepherd, Auggie. She follows directions well and has a great demeanor. Auggie and I look forward to working with her in the future!

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Ariel G.
Sitter Profile Image: Jasmine P.
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Jasmine P.
from
$30
per walk
5.0 out of 5 stars
99 reviews
38 repeat clients
10 years of experience
Kenwood, Chicago, IL, 60615

Jasmine is awesome. She has been such a help with our German Shepherd who loves her - and even trained her to walk much better within just a few days of walking her! We are so thankful to have a helping hand like Jasmine near to us - so we couldn’t recommend hiring her more highly (though not when we need her!! ?)

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H D C.
Sitter Profile Image: Cassandra B.
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Cassandra B.
from
$25
per walk
5.0 out of 5 stars
10 reviews
3 repeat clients
11 years of experience
Kenwood, Chicago, IL, 60615

About: I’ve loved animals since I was a kid. My many years of pet ownership has trained me for this opportunity. My Chewy is both happy and healthy. I’m recently retired. My daily schedule is built around the needs of my boy, Chewy. He’s walked at minimum three (3) times a day; my friends and family know the routine. I have a secure deck to allow fresh air and free movement with guaranteed security. I have a crate if needed, but think all dogs should have free movement daily.

Sitter Profile Image: Chelsea G.
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Chelsea G.
Star Sitter
from
$26
per walk
5.0 out of 5 stars
48 reviews
17 repeat clients
20 years of experience
Douglas, Chicago, IL, 60653

Chelsea is super patient and collaborative! She is dedicated to gaining my dog's trust as my dog's new and first ever walker.

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Cory H.
Sitter Profile Image: Ashley C.
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Ashley C.
from
$20
per walk
5.0 out of 5 stars
8 reviews
4 years of experience
Chicago, IL, 60615

About: I grew up taking care of family pets and have also loved sitting for friends and family over the years. I joined Rover in 2022 while in grad school because I missed having animals around and have been caring for dogs and cats since. Now I work from home and have lots of flexibility in my schedule for care! . What sets me apart? Your pet’s experience: a safe, calm, and of course, fun time. I’ll take the time to learn their quirks, shower them with plenty of love, and make them as comfortable as possible while their human is gone. I don’t have any pets and only take on one Rover client at a time so I can give your pet(s) the dedicated, individualized care they deserve. I also work from home and have lots of flexibility in my schedule. This means less stress, sticking more closely to the routine they’re used to, and no fighting for attention! . Your experience: I know how important it is to have a trustworthy sitter or walker while you’re away for peace of mind and I pride myself on being responsible, detail-oriented, and communicative. For every booking, I send plenty of photos of your pet living their best life and discuss your communication preferences ahead of time so we can be on the same page. I have a lot of flexibility in my daily schedule so I'm very happy to work with you to accommodate your needs or adjust if things change. For boarding, I live with my boyfriend in a spacious condo in Hyde Park, so there's plenty of room for your pet to play, get their zoomies out, or find a spot for some alone time. Although I'm the primary caregiver, he is also always up for a belly scratch or round of tug of war, so I consider him a nice bonus for your pet :) We live on a quiet one-way street on the top floor so there is minimal street noise and overstimulation. For house sitting, I know that your pets may be happiest in their own space, and I'm comfortable working in different environments to make sure they are safe and comfy! I will always be respectful of your space and communicative if any issues come up.

Sitter Profile Image: Qutress T.
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Qutress T.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
90 reviews
35 repeat clients
10 years of experience
Grand Boulevard, Chicago, IL, 60615

Q was great with Remi! She showed up ready to walk him and was prepared with any questions she had.

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Abi S.
Sitter Profile Image: Ian H.
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Ian H.
from
$20
per walk
4 years of experience
Hyde Park, Chicago, IL, 60615

About: I’ve always been the go-to among family and friends to watch their animals when they are gone for trips or vacations or need extra help. I’m an avid walker in general, and a walk is always better with a pet! I’ve volunteered for two years at animal shelters, trained and raised a puppy, and have experience caring for pets young and old. I’m currently a writer, remote copy-editor, and substitute teacher with an incredibly flexible schedule at the moment. I can watch, walk, and care for dogs and cats pretty much 24/7 at the moment. The only thing I cannot do is host animals in my home due to my apartment’s lease. Every pet is different and every pet owner cares for their pet differently. Let me know all your animals quirks and needs and I’ll meet them happily! I’d love to walk your dog around the park or neighborhood, give them them their special treats, respect your cat’s weird boundaries and quirks, etc, etc. :)

Sitter Profile Image: Page M.
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Page M.
from
$20
per walk
25 years of experience
Chicago, IL, 60637

About: I’m a lifelong animal lover with years of experience caring for dogs of all sizes, ages, and personalities. Before joining Rover, I regularly used Wag to walk and care for dogs, so I’m familiar with working with different breeds, temperaments, routines, and owner preferences. I’m new to Rover, but not new to dog walking or pet care. I’ve also cared for dogs in my own home and helped friends and family with their pets. I’m comfortable with energetic dogs, senior dogs, shy dogs, and dogs who need a little extra patience and attention. I enjoy long walks, exploring new neighborhoods, and making sure every dog gets the exercise, enrichment, and care they need. I live on Chicago's Far South Side, but most of my clients are in neighborhoods farther north, including Lincoln Park, Fulton Market, and nearby areas. I’m happy to travel for scheduled walks and drop-in visits, so I’m a good fit if you’re looking for a reliable walker or sitter who is willing to come to you. I’m happy to accommodate each dog’s routine, including feeding schedules, medications, special instructions, and plenty of updates while you’re away. Whether your dog needs a quick potty break, a long walk, or a reliable sitter, I’ll treat them like one of my own. Pet care is already a regular part of my daily routine through caring for my own dogs. I’m used to incorporating walks, feeding, play, training, and general care into my day and paying close attention to each dog’s individual needs. I currently work part-time, and I enjoy being active and spending time with animals. I have a fenced-in yard and two friendly dogs of my own, so I’m very comfortable managing dogs with different personalities, energy levels, and routines. When caring for pets in my home, I prioritize safety and make sure all dogs are comfortable with one another. In clients’ homes, I follow their routines and instructions closely and focus on keeping their pets safe, comfortable, and well cared for.

Sitter Profile Image: Evan P.
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Evan P.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
54 reviews
17 repeat clients
17 years of experience
Hyde Park, Chicago, IL, 60615

Thanks for walking Bailey! He was happy!

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Colleen F.
Sitter Profile Image: Elizabeth D.
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Elizabeth D.
from
$18
per walk
5.0 out of 5 stars
32 reviews
9 repeat clients
20 years of experience
Chicago, IL, 60609

Levi (Elizabeth) is an incredible sitter with my grumpy old dog! He’s a very difficult boy to work with and barks and barks at her, yet she is patient, kind, and gentle with him, meeting him on his terms. Highly, highly recommend!!

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Tammy M.
Sitter Profile Image: Jasmine R.
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Jasmine R.
from
$18
per walk
4.7 out of 5 stars
12 reviews
8 repeat clients
10 years of experience
Chicago, IL, 60653

Consistent, punctual, communicative, and generous. She shows up everyday in a timely manner, cares for my dog, and even gives complementary baths and cleaning if she makes a mess. HIGHLY RECOMMENDED 🤗 she offers a good range of services as well!!

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Nyla S.
Sitter Profile Image: Che Maria B.
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Che Maria B.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
29 reviews
8 repeat clients
10 years of experience
Hyde Park, Chicago, IL, 60615

She was great with my dogs who are shy at first. She gave me some great feedback and tips for walking my dogs and even came out in awful weather. Highly recommend!

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Julie G.
Sitter Profile Image: Maia S.
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Maia S.
from
$17
per walk
5.0 out of 5 stars
13 reviews
2 repeat clients
20 years of experience
Hyde Park, Chicago, IL, 60637

About: I’ve grown up with animals all my life and my house was always noisy. However, now that I’ve moved away from home I’ve been missing the little guys. Im going into a my Masters program at UChicago! I’m also a barista at Starbucks! I usually work in the early morning so my afternoons are pretty open! I have the upmost respect for others property and place. I would love to board animals at my apartment if you are comfortable with it! However, I will come second to only you in loving your animal.

Sitter Profile Image: Leah H.
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Leah H.
from
$17
per walk
4.8 out of 5 stars
8 reviews
1 repeat client
10 years of experience
Grand Boulevard, Chicago, IL, 60653

About: I am a CPR certified pet sitter who loves animals and loves to care for things. I have no pets of my own because I travel often for my full-time job . However. , I look forward to building a trust worthy, healthy relationship with you and your animal family. I currently work from home full-time so I have flexible hours. I do travel often for work so the further out I know for overnight days is the better. I also am available to walk dogs daily. I live alone and a very nice neighborhood full of lots of trees and families. I keep a very neat and nice home free of anything that could harm animals.

Sitter Profile Image: Syenna M.
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Syenna M.
from
$15
per walk
5.0 out of 5 stars
3 reviews
1 repeat client
8 years of experience
Hyde Park, Chicago, IL, 60615

About: I have experience caring for both energetic dogs who need structure and movement, as well as more sensitive pets who benefit from patience, gentle routines, and clear communication. I’m organized, responsive, and great at managing schedules—skills I use every day in my professional work and bring directly into pet care. I pay attention to details, follow instructions carefully, and make sure owners feel fully informed while they’re away. I’m a reliable and attentive weekend pet sitter based in Boston, and I take pride in creating a calm, safe, and caring environment for every animal I look after. I work a full-time remote job during the week, but on weekends I’m fully dedicated to pet care—whether that means long walks, dedicated playtime, or simply keeping your pet company and relaxed at home. As someone who values consistency and trust, I make sure every pet gets thoughtful, individualized attention. Whether your pet needs slow, steady walks, a playful activities, or lots of affection, I’m here to help your weekend feel stress-free. If you’re looking for a sitter who is responsible, communicative, and truly loves spending her weekends with animals, I’d love to support you and your pet!

Sitter Profile Image: Katarina S.
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Katarina S.
from
$16
per walk
5.0 out of 5 stars
3 reviews
1 repeat client
8 years of experience
Hyde Park, Chicago, IL, 60615

About: I’ve taken care of multiple dogs of varying ages and have always enjoyed it immensely. I no longer have a dog of my own but I would love to make friends with yours. I am working 3 days per week (not a set schedule) and have enough time to spend with some lovely dogs. My schedule changes week to week but I am quite flexible and hopeful we can find a good agreement for dog sitting/walking. My apartment is clean and spacious and perfect for a small/medium dog to stay at and play. I do not own a crate but also would prefer if your dog is properly trained and can tolerate being in open space.

Sitter Profile Image: Huibo L.
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Huibo L.
from
$19
per walk
5.0 out of 5 stars
1 review
2 repeat clients
10 years of experience
Hyde Park, Chicago, IL, 60615

About: I’ve taken care of my own dog and cat for 7 years and before then was the go to sitter for all my friends with pets! I’m also a PhD student in psychology working in animal behaviors. Since young, I understand animals and respect them: how we treat them influences their behaviors. I’ve got the heart and the training to give your babies the best care they deserve when you are away! My schedule is flexible as long as we communicate in advance. Mornings work the best at the moment but let me know what you need I’ll try to make it work :) I have a comfy apartment with one dog and one cat. They’ll keep your baby company if you board with us. I’m skilled in introducing new animals to each other, I try to adjust to each animals temperaments. On other visits I try to get to your babies first as well, and of course your tips are always appreciated as you know them the best!

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The median cost per walk for dog walking in Kenwood is $20

Dog parents share their Rover experiences - Kenwood

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5.0 out of 5 stars

Levi (Elizabeth) is an incredible sitter with my grumpy old dog! He’s a very difficult boy to work with and barks and barks at her, yet she is patient, kind, and gentle with him, meeting him on his terms. Highly, highly recommend!!

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Tammy M.
Dog Walking
5.0 out of 5 stars

super accommodating and helpful, my dog walker/family friend recently passed and it has been difficult finding decent walkers but she was fantastic. super friendly and very understanding and worked well with Leviathan

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Sophia T.
Dog Walking
5.0 out of 5 stars

Victoria always goes above and beyond in her communication and service. She is a caring and responsible dog walker. I highly recommend her!

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Ariel G.
Dog Walking
5.0 out of 5 stars

Evan was easy to communicate with and walked our Australian Shepherd almost two miles in just half an hour. I appreciated him giving our pooch the extra exercise!

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Ariel G.
Dog Walking
5.0 out of 5 stars

Chelsea is super patient and collaborative! She is dedicated to gaining my dog's trust as my dog's new and first ever walker.

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Cory H.
Dog Walking
5.0 out of 5 stars

Amiyah was great with my dog while I was out the country. Was always on time and informative with updates and pictures daily. I highly recommend her and I will be booking her my next trip I have. 👍🏽💪🏽

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Justin C.
Dog Walking
5.0 out of 5 stars

Emma did a wonderful job walking my two dogs. She was very responsive and made the whole process great. Highly recommend.

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Rylee M.
Dog Walking
5.0 out of 5 stars

Annie is amazing! Highly recommend her for all pet needs. She is very communicative and engaged. Our dog is a bit shy but Annie was able to make our dog feel incredibly comfortable and open with her. We are so grateful for her services!

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Angelina L.
Dog Walking
5.0 out of 5 stars

Jozelin took Leo on morning walks while I was out of town for a few days. She followed my instructions, was respectful of the space, & was able to handle my Leo. Will book again!! Tyyy

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Cassidy C.
Dog Walking
5.0 out of 5 stars

Tamara is amazing!! She is reliable, responsible and flexible. She handled my dog’s special needs with no problem. Even gave him a bath. Knowing she was taking care of my dog gave me peace of mind while I was away. I highly recommend Tamara!!!

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Kelly N.
Dog Walking
5.0 out of 5 stars

One of the best I’ve experienced on this app so far. Bola was very effective, communicative and a joy to work with! Django loves her so much! I highly recommend her for your pet!

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Johnathan M.
Dog Walking
5.0 out of 5 stars

Lillian is the best! Always accommodating of our changing schedules and takes great care of our dog. She has been walking our dog weekly for several months now and we have had zero issues. Thanks Lillian!

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Hung C.
Dog Walking
5.0 out of 5 stars

Zoe is great with Kaia. We appreciate all the kind consideration in making sure that Kaia’s walk is safe and enjoyable. All the poop shots 😁and updates are great!!!😊

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NORMA L.
Dog Walking
5.0 out of 5 stars

It was a pleasure working with Chauntrell to walk my boy! I received great progress pics and solid communication during the process. I appreciate knowing my son was well taken care of while I couldn’t be home. Thank you, Chauntrell!

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Melissa M.
Dog Walking
5.0 out of 5 stars

Julia was absolutely wonderful with my pooch! My pup took to her right away. She was very communicative and flexible with accommodating my last minute requests. And with each walk I received pics and my pup couldn’t have looked happier! 😊

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Jasmyn M.
Dog Walking
5.0 out of 5 stars

Taylor took very good care of my dog and did very well adapting to his needs during her first time watching him. I very much appreciated her help while I was out of town.

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Justin R.
Dog Walking
5.0 out of 5 stars

Excellent dog walker. She is dependable, trustworthy, and amazing with my dog. I felt completely comfortable leaving my pet in her care during my vacation. She responds is a great timely manner

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Lashemia B.
Dog Walking
5.0 out of 5 stars

Our tow pups had a great time with Manuela! Such an ease for the service and so much love was given. Thank you!

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Laura Y.
Dog Walking
5.0 out of 5 stars

If not for Erin moving away we would not let her go :) Erin has been walking Harry every week for several months and Harry knows and looks forward to the days where he gets to see her! We appreciate her consistent care and patience with Harry, who is a sweetheart but can be reactive, and Erin has always handled him wonderfully. And I so appreciate the sweet notes and model shots Erin sends each walk! 100/10 rating!

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Abby J.
Dog Walking
5.0 out of 5 stars

I had a last minute request and Nikki was very caring from the start! She walked my beloved Gio like a pro. Efficient and polite.

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luanda
Dog Walking
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