Dog Walking Kenwood

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

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Over 87
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: Huibo L.
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Huibo L.
Star Sitter
from
$19
per walk
5.0 out of 5 stars
• 6 reviews
6 repeat clients
10 years of experience
Hyde Park, Chicago, IL, 60615

“Amazing and very detailed walker! You won’t be disappointed 😇”

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

“Qutress is so sweet to our Ellie and we are so lucky to have found her.”

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Melody H.
Sitter Profile Image: Candace M.
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Candace M.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
• 19 reviews
9 repeat clients
14 years of experience
South Side, Chicago, IL, 60653

About: Hi, I’m Candace! I’m a caring and experienced pet sitter who believes dogs are family. I previously offered pet sitting before taking some time away due to working in office and also caring for my senior dog, Francesca who has since passed. After taking time to grieve the loss of my beloved girl, I’m excited to return to something I truly enjoy: caring for animals. I offer pet sitting, dog walking, and drop-in visits. Whether your pup needs a walk, a potty break, a meal, or some extra attention while you’re away, I’m happy to help. For boarding, your dog will enjoy plenty of attention, two or more walks a day, treats, cuddles, and indoor playtime. I’m happy to follow your instructions for feeding, medications, routines, and special needs. I prefer housebroken dogs but am also comfortable with pups who use potty pads. I’ll provide regular updates and photos so you can feel at ease knowing your fur baby is happy and well cared for. I look forward to meeting you and your fur baby! I currently work from home. Depending on the day/time of your dog's visit I may have an errand or an appointment to attend to. However, I'm not away for more than a couple of hours. I can alert you to any change in this pattern. I can accommodate most requests. I will care for your dog based on your specifications. I treat all my guests like they’re my own dog.

Sitter Profile Image: Erin M.
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Erin M.
from
$22
per walk
5.0 out of 5 stars
• 22 reviews
10 repeat clients
2 years of experience
Hyde Park, Chicago, IL, 60637

“Erin has been absolutely amazing with Oscar. She walks him every day, is always on time, and consistently goes above and beyond. I really appreciate the detailed updates and photos after each walk — it gives me peace of mind knowing he’s in such good hands. She’s also so thoughtful with my cats and always takes time to give them attention too, which means a lot. It’s clear she genuinely cares about the animals she works with. Highly recommend Erin to anyone looking for someone reliable, caring, and communicative!”

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Brady P.
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: 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: Andrea W.
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Andrea W.
from
$19
per walk
6 years of experience
Kenwood, Chicago, IL, 60615

About: I am experienced in very detailed pet care instructions and understand that those pets have unique needs. I have experience with administering medical supplements, adhering to specific feeding schedules and portion requirements. I have followed individualized activity plans and routines for both dogs and cats. I want to provide the consistency in a pets routine while their owners are away. I promote owner-established potty training methods in regards to 6 months and older potty training behaviors. My approach combines reliability, patience, and genuine affection for animals while providing pet owners with confidence that their pets are receiving attentive and compassionate care in their absence. I am a Retired NCAA WBB coach so I have time to care for your fur family! I Can adjust to your pets favorite routine! I stay in your home so that your fur family is in their most safe space! I stick to their routines and routes! I can include new enrichment activities and stick to what works for them! I understand crating and routine! I have also slept w 4 animals in bed so that were very supported during the owner’s mini vacation.

Sitter Profile Image: Alina M.
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Alina M.
from
$15
per walk
4 years of experience
Chicago, IL, 60637

About: I am a writer and artist by day and absolutely love animals! I'm looking to share my extra time caring for your furbabies! I have experience walking, feeding, monitoring, and caring for dogs (large-small, puppy-senior), reptiles, small animals (rabbits, guinea pigs, rats, hamsters, ferret etc.), I have my own pets including, two terrier mixed dogs, an American bull toad, and a free roam rabbit. I have cared for my family's dog as well. I am available during the weekdays, Monday-Friday mornings and afternoons. My weekends vary based on my availability but I can be flexible and discuss more in consultation. I have my own vehicle so I am able to check in and care for your pet, and help them at a moments notice in case of emergency's, I have a large fenced in yard at home that allows for plenty of space for your fur baby to explore, walk and play for a few hours.

Sitter Profile Image: Bola A.
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Bola A.
from
$30
per walk
4.9 out of 5 stars
• 188 reviews
77 repeat clients
15 years of experience
Hyde Park, Chicago, IL, 60637

“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.
Sitter Profile Image: Lainey B.
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Lainey B.
from
$10
per walk
10 years of experience
Hyde Park, Chicago, IL, 60615

About: I have owned pets since I was a kid, specifically dogs. I have been dog/cat sitting and housesitting for family and friends for the past 5 years, and I am ready to expand my services to others. I work as a barista, so I am the perfect candidate to watch your pup for last minute trips. My schedule is very flexible so reach out! I will give your pets my undivided attention while you are gone so that they feel loved and cared for. I have no problem with difficult pets as well, I don’t judge!

Sitter Profile Image: Grace H.
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Grace H.
from
$25
per walk
5.0 out of 5 stars
• 6 reviews
3 repeat clients
9 years of experience
Woodlawn, Chicago, IL, 60637

About: I have experience taking care of dogs, cats, ducks, chickens, frogs, and fish. I am able to stay over or transport to your house, making sure your pets feel safe and cared for! I am currently a student and will be able to stop by in the morning or afternoon/night or stay at your house to care for your pet! I will ensure your pets are properly nourished and entertained. I listen carefully to safety requirements for your house and will make sure your pet stays properly protected!

Sitter Profile Image: Nicole A.
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Nicole A.
from
$25
per walk
5.0 out of 5 stars
• 6 reviews
1 repeat client
15 years of experience
Woodlawn, Chicago, IL, 60637

About: I’ve always been the one my family goes to train our pets ever since we got our first dog; and it’s been my favorite job ever since! I love learning about different breeds but most importantly how to speak their language. From puppies to elderly cats, I’m happy to care for your fur babies. I’m a recent Masters student at UChicago and have full availability! From mornings to overnight stays, I’m happy to be there for a walk or drop in. My own pups thrive on routine but it’s understandable if yours enjoy that nonchalant schedule. I do think play time, mental stimulation, and a local sniffari is the best way for a good nights sleep. On our walks, I’ll try to make the most of our time together by seeing what environments they feel most safe in.

Sitter Profile Image: Jozelin R.
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Jozelin R.
from
$19
per walk
5.0 out of 5 stars
• 39 reviews
19 repeat clients
15 years of experience
Bridgeport, Chicago, IL, 60616

“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.
Sitter Profile Image: Tabbie M.
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Tabbie M.
from
$15
per walk
5.0 out of 5 stars
• 11 reviews
3 repeat clients
7 years of experience
Grand Crossing, Chicago, IL, 60619

“I booked Tabbie to walk our doggies and she was a lifesaver these past couple of days. Tabbie was very responsive, prompt, courteous and on time. She even asked if I wanted to walk them longer which I appreciated that a lot. A tired dog is a good dog and they were nice and tired. I will definitely be using Tabbie for more dog walks!”

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Shada H.
Sitter Profile Image: Tamya O.
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Tamya O.
from
$30
per walk
5.0 out of 5 stars
• 5 reviews
1 repeat client
4 years of experience
Grand Boulevard, Chicago, IL, 60653

About: I have hands-on experience caring for dogs of all sizes, breeds, and energy levels, including active and strong working breeds. I focus on creating a safe, structured, and stress-free environment while making sure every dog gets the attention, exercise, and care they need. I’m comfortable with walks, feeding schedules, crate routines, basic obedience reinforcement, and handling energetic dogs with patience and consistency. Pet parents can expect dependable communication, regular updates, and someone who genuinely treats their dogs like family. Your dog’s safety, comfort, and routine come first. A typical day includes structured walks, playtime, exercise, water breaks, feeding according to your instructions, and plenty of attention. I keep a calm and clean environment while making sure each dog gets the right balance of activity and rest based on their personality and needs. I’m especially comfortable with active and strong breeds, so dogs that need confidence, structure, and engagement are in good hands. Whether your pet needs a relaxed companion, exercise, or consistent care while you’re away, I aim to make the experience stress-free for both you and your dog. You’ll receive updates, photos, and quick responses throughout the stay so you always know how your dog is doing.

Sitter Profile Image: Lillian M.
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Lillian M.
from
$25
per walk
5.0 out of 5 stars
• 32 reviews
9 repeat clients
13 years of experience
Armour Square, Chicago, IL, 60616

“Lillian has been great with my dogs and very communicative throughout the walks. She took the time to make sure they were comfortable, shared updates and photos, and went above and beyond with their care. I really appreciated her flexibility and willingness to work with my schedule, especially while I was out of town. I felt confident knowing my dogs were in good hands, and I would absolutely recommend her to other pet parents.”

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Carla T.
Sitter Profile Image: Mariam A.
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Mariam A.
Star Sitter
from
$17
per walk
5.0 out of 5 stars
• 56 reviews
15 repeat clients
4 years of experience
Near South Side, Chicago, IL, 60605

“Strong communicator and sweet energy with my pets. I was nervous about hiring a dog walker and Mariam helped put me at ease by demonstrating her trustworthiness.”

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Heather M.
Sitter Profile Image: Beverly B.
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Beverly B.
Star Sitter
from
$22
per walk
5.0 out of 5 stars
• 279 reviews
107 repeat clients
7 years of experience
Chatham, Chicago, IL, 60620

“We have been consistently using Beverly since our pup was 3 months old. Beverly does weekly walks for us as well as daycare and overnight stays. Charley loves her Beverly and she has quickly become part of our family.”

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Sandy M.
Sitter Profile Image: Brittani H.
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Brittani H.
from
$20
per walk
5.0 out of 5 stars
• 2 reviews
1 repeat client
30 years of experience
New City, Chicago, IL, 60609

About: I’ve taken care of a variety of pets, from puppies, kittens, small dogs, large dogs and more. Senior dogs with medicinal needs are a breeze! I work remotely and have plenty of time to play with your pups and cats! I have two pups of my own who hang out with me and my partner all day! I have a fenced-in yard and two friendly pups who love to sun bathe. We love a game of tug or fetch and we love to snuggle.

Sitter Profile Image: May K.
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May K.
from
$20
per walk
10 years of experience
Near South Side, Chicago, IL, 60616

About: I’ve always had a dog in my household and understand the need for love, play, and care. My parents have a samoyed and border collie, which are highly active dogs, and I make it my priority to spend time with them outside whenever I visit home. I’m currently unemployed so I’m available from 9-4 during the weekdays. I can also do weekends, but my schedule changes every so often but can be worked out! I have plenty of toys, trees, scratchers, and space to watch your pets. I do not use plug-in scents, candles, or any harsh cleaning chemicals.

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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

Che is wonderful! Keeps our dog calm & happy and always keeps us posted on the walk with plenty of updates for peace of mind.

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Teresa F.
Dog Walking
5.0 out of 5 stars

Tamara did a wonderful job with our dog Sandy! We were so nervous about leaving her in our home while gone for the weekend. But Tamara made us comfortable, frequently checking in and entertaining my many questions. She even provided medical care as Sandy had injured her eye prior to our departure. We are so happy to have found someone we trust to watch our Sandy and would wholeheartedly recommend her to others.

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Dara B.
Dog Walking
5.0 out of 5 stars

Huibo was wonderful! Communicative and followed instructions perfectly, and my dog clearly loved her. Will absolutely book her again!

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Rachel S.
Dog Walking
5.0 out of 5 stars

Kiera does a great job taking care of our nervous dog who is also special needs, and keeps you updated on all walk activities! She is great!

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Madeleine P.
Dog Walking
5.0 out of 5 stars

Much thanks to Lucille for ever being reliable!! She was able to treat our pup for a walk before her travel plans on a very short notice!!! Thank you!!!

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NORMA L.
Dog Walking
5.0 out of 5 stars

Danielle was an incredible help with a very last minute booking. She was professional, polite, and friendly throughout the entire process. My dog absolutely loved her, which gave me great peace of mind. I would definitely book with Danielle again and highly recommend her to anyone looking for a reliable, caring dog walker.

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Jack I.
Dog Walking
5.0 out of 5 stars

Syenna was so responsive and wonderful with Ollie. We look forward to using her services again. Thank you!

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Yulia G.
Dog Walking
5.0 out of 5 stars

Emily did a wonderful job of walking my two dogs. She was able to accommodate a last minute request which I greatly appreciated. Highly recommend!

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Rylee M.
Dog Walking
5.0 out of 5 stars

Sarah is great with my dog, Mushu. I have booked her for house sitting and for one-off walking and she is fast with communication, flexible with timings, and a great house guest. Mushu is a little protective but likely thinks that Sarah is now a part of the household which is a win in my books. I will continue to book her.

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Ramanujan S.
Dog Walking
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

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

Erin was nice to work with and communicated well while planning Mazi’s walks! Would love to book again when shes available 😊

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Austin S.
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
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