Dog Walking in Woodlawn, Chicago, IL

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Top rated Woodlawn dog walkers

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Sitter Profile Image: Whitney R.
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Whitney R.
from
$13
per walk
2 years of experience
Woodlawn, Chicago, IL, 60637

About: I have hands on pet care experience, regularly caring for family and friends’ dogs. I follow their routines, provide morning and walks & timely feeding. Pet care naturally fits into my routine because I enjoy being active and taking walks, making it easy to keep dogs happy, healthy and cared for. I respect both pets and their homes, ensuring safety, comfort, and reliable care while following routines so pets feel secure, loved and well looked after.

Sitter Profile Image: Danielle K.
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Danielle K.
from
$15
per walk
5.0 out of 5.0 stars
5 reviews
2 repeat clients
8 years of experience
Woodlawn, Chicago, IL, 60637

About: I have pet sit all kinds of loving dogs. Since I was 15 My family, friends and neighbors have trusted me to walk, feed, play with and care for their pets. I work full time virtually, so I am flexible and can care for your beloved pups while at home. I only have availability to do overnight boarding on weekends. I have a spacious place for your dog to have plenty of room to play and be comfortable. In addition, I have a dog park and a spacious park/field a walk away from my home. There also is a trail for us to walk as well. I am equipped to feed, walk and sing to your pup.

Sitter Profile Image: Rebecca B.
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Rebecca B.
from
$25
per walk
5.0 out of 5.0 stars
25 reviews
4 repeat clients
10 years of experience
Woodlawn, Chicago, IL, 60637

Rebecca is so reliable! She walked Spot on a regular schedule for 2 months and it was a relief knowing that someone was giving my pup a great midday walk and some love while I was at work.

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Michaela J.
Sitter Profile Image: Leah H.
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Leah H.
from
$17
per walk
5.0 out of 5.0 stars
5 reviews
10 years of experience
Hyde Park, Chicago, IL, 60615

While I was out of town this weekend, Leah handled everything with my mom and she couldn’t stop saying how great Leah was with Jaxson and how friendly she was.

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S W.
Sitter Profile Image: Manuela G.
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Manuela G.
from
$23
per walk
5.0 out of 5.0 stars
23 reviews
7 repeat clients
20 years of experience
Woodlawn, Chicago, 60637

Manuela did a great job! My dog Ella really enjoyed walking with her. Manuela is punctual, reliable. My dog doesn't trust people easily but with Manuela, it was easy. Amazing! Thank you so much. ?

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Sue K.
Sitter Profile Image: Katarina S.
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Katarina S.
from
$16
per walk
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: Katerina L.
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Katerina L.
from
$15
per walk
4.9 out of 5.0 stars
21 reviews
8 repeat clients
5 years of experience
Hyde Park, Chicago, IL, 60637

She was great with Bumpy. I got photos daily.

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Jocilyn F.
Sitter Profile Image: Dominique L.
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Dominique L.
from
$22
per walk
4.9 out of 5.0 stars
47 reviews
21 repeat clients
5 years of experience
Woodlawn, Chicago, IL, 60637

Mack has been loving having Dominque walk him during the week! She’s been very prompt and always lets me know when she starts and ends her walk.

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Dianna T.
Sitter Profile Image: Kaitlin R.
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Kaitlin R.
from
$25
per walk
5.0 out of 5.0 stars
17 reviews
9 repeat clients
7 years of experience
Kenwood, Chicago, IL, 60615

Kaitlyn is the only walker on Rover that I would actually have a key cut for. She is very professional, punctual, and respectful with your pup.

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Kodi R.
Sitter Profile Image: Agustina P.
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Agustina P.
from
$25
per walk
5.0 out of 5.0 stars
4 reviews
1 repeat client
10 years of experience
Woodlawn, Chicago, IL, 60637

About: I have extensive pet care experience that began in my childhood. Growing up, I was responsible for a variety of pets, including dogs, cats, and small mammals. This early exposure taught me the essentials of animal care, from feeding and grooming to understanding their behaviors and health needs. Over the years, I have honed my skills in providing attentive and compassionate care, ensuring that each pet feels loved and well-tended. This lifelong passion has equipped me with the knowledge and empathy necessary to handle a wide range of pet care responsibilities confidently. I work from home and I am a home body except when I walk outdoors, run or bike! A walk is so much better with a dog I have plenty of space for dogs to run as I has a long hallway and a downstairs! I have parks 2 blocks down where I live and a dog area.

Sitter Profile Image: Erin S.
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Erin S.
from
$20
per walk
5.0 out of 5.0 stars
3 reviews
1 repeat client
15 years of experience
Hyde Park, Chicago, IL, 60615

My dog Harry and I have so far loved Erin and will be continuing to book her for walks. I know Harry loves Erin’s care and patience while he sunbathes, and I always appreciate the notes and photos she leaves on rover cards + appreciate her flexibility. Thank you!

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Abby J.
Sitter Profile Image: Qutress T.
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Qutress T.
Star Sitter
from
$20
per walk
5.0 out of 5.0 stars
76 reviews
27 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: Lynettra L.
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Lynettra L.
from
$19
per walk
4.9 out of 5.0 stars
36 reviews
15 repeat clients
10 years of experience
Kenwood, Chicago, IL, 60653

About: Hi, I’m Lyn— a professional pet care provider and lifelong animal lover. With over 10 years of hands-on experience walking, sitting, training, and loving dogs, I bring both skill and heart to every pup I care for. Whether it’s playtime, walks, structured training, or cozy cuddle sessions, your dog will be treated like family. I specialize in reading dog body language, adapting to individual temperaments, and providing a safe, enriching experience tailored to your pet’s needs. I currently work part-time at a respected dog daycare and training facility, giving me both the knowledge and flexibility to support you and your pup. I welcome all breeds and behavior levels — including dogs with special needs or training challenges. I believe in meeting dogs where they are and working with positive reinforcement, consistency, and love. Let’s set up a meet-and-greet so you can feel confident and comfortable. Your dog’s happiness and your peace of mind are my top priorities. I currently work part-time at a dog daycare and training facility, which gives me plenty of flexibility to dedicate time, energy, and love to your pup! Whether it’s walks, enrichment, or downtime, I have the capacity to provide focused, attentive care throughout the week. I tailor my care to each dog’s individual needs and routines. Whether your dog is crate-trained, free-roaming, or uses gates within the home, I will follow your existing structure to ensure consistency and comfort. My goal is to provide a safe, familiar environment that supports your dog’s well-being and helps them thrive while you’re away.

Sitter Profile Image: Anna J.
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Anna J.
from
$20
per walk
23 years of experience
Hyde Park, Chicago, IL, 60615

About: Since I was a kid I’ve had experience caring for a plethora of animals. Growing up we had cats, dogs, chickens, ducks, rabbits and even goats. I’m experienced with kittens and puppies as well as senior pets. I also have experience administering medications to cats and dogs. I currently work part time, so I have a very flexible schedule and can drop in regularly or on an as needed basis depending on what your pet needs! I have a calm demeanor and do my very best to help pets feel comfortable and respected. I know every pet has different needs and I do my best to listen to what theirs are and ensure they get quality care and affection.

Sitter Profile Image: Bola A.
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Bola A.
from
$30
per walk
4.9 out of 5.0 stars
146 reviews
45 repeat clients
15 years of experience
Hyde Park, Chicago, IL, 60615

Mother-in-law said Stella LOVED Bola and was so excited for all her walks!! The only thing she would change to make this a 5 start rating was the inconsistancy of arrival time and lack of communication in regards to being late. Overall, amazing service!! We look forward to working with Bola again in the near future!!

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Bridgette J.
Sitter Profile Image: Monique O.
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Monique O.
from
$30
per walk
5.0 out of 5.0 stars
4 reviews
25 years of experience
Chicago, IL, 60637

About: I have taken care of dogs my entire life , I was a baby who grew up with a Irish Setter. and so my life's journey has been traveled with My best buddies . My family and my pets. Their love and kindness cannot be measured and they deserve the very best of care. I pride myself on training tips and methods i have used on puppies to older dogs i’ve taught behavior adjustments. I believe a healthy fit pup is a happy one . I was also involved in a program we called visiting buddies , taking puppies to spend time with senior citizens and pre school students. throughly enjoyed by everyone involved. I am currently working part time and my schedule is flexible, I work in events. my availability is after 12 for walking and boarding generally but with enough notice I can work some morning hours. I have a large fenced yard as well as a dog run on the side of our home. I have a very friendly furry baby who will give your pup hours of entertainment. I you. would prefer. your pup was crated I. have a very large kennel indoors as well as outside. My home has tons of space .

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

About: I cared for and helped train my family's Australian Shepherd and have cared for dogs of all ages and breeds. Comfortable working with all dogs. Open to various tasks and responsibilities. Able to accept both one-time and recurring bookings for both cats and dogs. Happy to accept new bookings as needed. I make sure to follow the wishes of the owner to ensure the dog's routine is disrupted as little as possible. I am happy to follow instructions to ensure the dog is comfortable.

Sitter Profile Image: Rina S.
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Rina S.
from
$30
per walk
4.8 out of 5.0 stars
29 reviews
9 repeat clients
10 years of experience
Woodlawn, Chicago, IL, 60637

About: “With over 10 years of experience caring for dogs of all breeds, sizes, and personalities, I’ve had the joy of looking after pets for family, friends, and neighbors. From playful puppies to senior companions, I know how to provide the right balance of love, attention, and reliable care. Every dog I care for is treated like part of my own family—with plenty of cuddles, walks, and tail-wagging fun!” Available full-time to give your pets all the love, walks, and attention they nee any day of the week They will not lack anything, they will enjoy it all the time. Your pet’s safety and happiness are always my top priority. I provide responsible and loving care in a clean, safe environment, while also being mindful of nature during walks and outdoor time. With me, your furry friend will be in caring and reliable hands.

Sitter Profile Image: Raven F.
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Raven F.
from
$20
per walk
5.0 out of 5.0 stars
3 reviews
1 repeat client
10 years of experience
Washington Park, Chicago, IL, 60637

About: I am a long-time animal lover who grew up with and cared for our dogs and cats in the home. I even have a pit bull terrier of my own at home now! I'm looking to use my knowledge of animal care to help other dog owners care for their pooches while they're away. I am comfortable around pets of all sizes and energy levels and will work well to adjust to your specific pet's needs. My own pooch has some reactive tendencies, so if your pet is the same just know that I know that they're just anxious about something going around them and I'm quick to make adjustments so they're more comfortable. There is no job that I will stray away from when it comes to animal care, including cleaning up any messes your pet may make. I am extremely dedicated to providing the best animal care and hope to do business with you in the near future. :)

Sitter Profile Image: Jasmine R.
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Jasmine R.
from
$18
per walk
4.5 out of 5.0 stars
7 reviews
4 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.
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