Pet Sitting Woodlawn

Book a pet sitter to stop by your home a few times a day to feed and play with your pet.

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Over 91
pet parents in Woodlawn have booked pet sitting

Woodlawn, Find top rated pet sitting

Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Manuela G.
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Manuela G.
from
$12
per visit
5.0 out of 5 stars
• 28 reviews
8 repeat clients
20 years of experience
Woodlawn, Chicago, IL, 60637

“I am very glad that Manuela helped with my cats during our vacation. Manuela came before my trip to meet Mia and Aska, and then came on all the appointed days. Sent me photos and videos of them playing together. I can recommend Manuela as an excellent nanny for kittens :)”

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Tatyana U.
Sitter Profile Image: Coretta S.
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Coretta S.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
• 315 reviews
106 repeat clients
3 years of experience
South Shore, Chicago, IL, 60649

“This is my second time using Coretta to watch my pets and she was just as amazing as the first. Her updates are so thorough, thoughtful, and sweet and can tell she genuinely enjoys caring for my animals.”

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TaKara H.
Sitter Profile Image: Sarah W.
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Sarah W.
from
$17
per visit
5.0 out of 5 stars
• 4 reviews
1 repeat client
3 years of experience
Woodlawn, Chicago, IL, 60637

About: Taking care of dogs was the first job I ever had. Neighbors would have me come over after school to check in with their babies and play with them or take them on walks. I've also been lucky enough to watch people's dogs while they were out of town; including puppies! Most recently, I volunteered at an animal shelter where we would take animals for walks, train them, bathe them, and shower them with love and treats! Every dog is unique, and I enjoy taking the time to get to know each animal and their family. I am currently working part-time with a flexible schedule, so I have plenty of time to accommodate specific schedules and adapt to individual needs. I always approach caring for animals with safety and respect as a first priority. It is important to me that both the dog and I are safe, and that I am attuned to their needs. I also want to prioritize respect for other people's space and time, so I make an effort to always be on time and adapt to any individual requests in people's homes.

Sitter Profile Image: Evan P.
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Evan P.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
• 58 reviews
17 repeat clients
17 years of experience
Hyde Park, Chicago, IL, 60615

“Evan did a wonderful job watching our cat for a long weekend. He was communicative and responsive, which made us feel comfortable and confident that our cat was in great hands.”

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Anna B.
Sitter Profile Image: Syenna M.
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Syenna M.
from
$15
per visit
5.0 out of 5 stars
• 5 reviews
3 repeat clients
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: Jordan F.
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Jordan F.
from
$18
per visit
10 years of experience
Hyde Park, Chicago, IL, 60637

About: I have been around and cared for dogs for years through family, friends, and everyday life. I’ve been trusted to feed them, take them outside, go on walks, play with them, check in throughout the day, and give them plenty of attention. I understand that every dog has their own personality and routine, and I enjoy taking the time to make them feel safe and comfortable. My schedule is flexible, which gives me availability in the mornings, afternoons, and evenings depending on the day and what you need. I’m available throughout the week and on select weekends, and I’m happy to work around your pet’s normal routine whenever possible. I know how important it is to trust someone coming into your home and caring for your pet. I always respect your space, follow the routine and instructions you provide, and make sure your pet feels safe and comfortable. Whether it’s feeding, walks, playtime, litter care, or simply keeping them company, I want them to feel cared for while you’re away. I’ll also keep you updated with pictures 🤗so you can stay up-to-date with your pet.

Sitter Profile Image: Huibo L.
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Huibo L.
Star Sitter
from
$17
per visit
5.0 out of 5 stars
• 3 reviews
4 repeat clients
10 years of experience
Chicago, IL, 60615

“The best summaries I’ve ever received from a pet sitter here on Rover. Will definitely book again with Huibo in the future!!”

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Dominique L.
Sitter Profile Image: Qutress T.
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Qutress T.
Star Sitter
from
$17
per visit
5.0 out of 5 stars
• 92 reviews
35 repeat clients
10 years of experience
Grand Boulevard, Chicago, IL, 60615

“I am always very nervous when I leave my furry girl alone. It was the first time we booked Qutress and she did it amazing. On a couple days did a great bond and my Kira is always scared to everyone, she really had the touch, the care and patience for her. Qutress is reliable, careful with all details and kind. I would repeat her service as much I need it.”

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Carmen C.
Sitter Profile Image: Pratik J.
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Pratik J.
from
$20
per visit
10 years of experience
Woodlawn, Chicago, IL, 60637

About: I've been with pets all throughout my life. I've taken care of dogs, cats, rabbits, tortoises, parrots and fishes. I have a labrador Casper and a golden retriever, Remmy back home in Nepal, whom I miss every day. So I'm just looking for ways to spend more time with pets here. I work remotely as a software engineer, so my work schedule is flexible. I have lots of free time during the day, so I'm looking to walk dogs. In the past, I've walked dogs to the lake which is just 30 mins walk from home and I just chill at the lake with the dogs I'm taking care of, and also get some minor work done on my laptop. I live in a two bedroom apartment, so there's enough space for a pet. I usually walk dogs to the lake, which is just 30 mins walk from my place.

Sitter Profile Image: Laura O.
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Laura O.
from
$19
per visit
4.9 out of 5 stars
• 116 reviews
36 repeat clients
2 years of experience
Chicago, IL, 60615

“Laura took great care of my cat over the Labor Day weekend. He needed stop in visits 2x a day so he could get his wet food. Laura even gave him treats and played with him while she was there.”

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Jamie B.
Sitter Profile Image: Claire P.
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Claire P.
from
$17
per visit
5.0 out of 5 stars
• 10 reviews
3 repeat clients
12 years of experience
Woodlawn, Chicago, IL, 60637

“Communicated so well and was super kind! Very responsive and helpful!”

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Vanessa C.
Sitter Profile Image: Grace H.
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Grace H.
from
$22
per visit
5.0 out of 5 stars
• 6 reviews
3 repeat clients
9 years of experience
Woodlawn, Chicago, IL, 60637

“Amazing! Grace followed instructions & took the very best care of my shy girl Megatron! :) Megatron was super comfortable around Grace & was so well taken care of! Thank you Grace!”

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Clarissa G.
Sitter Profile Image: Danielle L.
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Danielle L.
from
$18
per visit
5.0 out of 5 stars
• 5 reviews
10 years of experience
Hyde Park, Chicago, IL, 60615

About: Hi, I'm Danny! I work part-time as a dog handler at a local daycare and have 10 years of experience caring for animals professionally through dog walking and pet sitting services. As a lifelong dog owner, I understand that pets are our family and I'm intentional about providing them with the genuine love and care they deserve. I provide reliable daily walks, drop-in visits, in-home pet sitting, and boarding tailored to your pet's unique personality and routine. Managing dogs and cats of all temperaments daily has taught me exactly how to keep your pet safe, happy, and well cared for. I am fully insured and First Aid/CPR certified, and I promise to treat your pet like one of my own! I'm currently working part-time while studying on my own schedule. I'm very flexible for dog walks, pet sitting, and drop-in visits most days of the week. I care for every pet based on their individual needs, personality, and routine. On walks, I focus on enjoying safe, fun exercise and giving them plenty of time to sniff and explore. For drop-ins and in-home sitting, I follow your instructions closely and make sure your pet has fresh food and water, exercise, playtime, cuddles (if they want them), and a clean, comfortable space. I’ll also send daily photos and report cards so that you have peace of mind while you’re away.

Sitter Profile Image: Dominique L.
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Dominique L.
from
$25
per visit
4.9 out of 5 stars
• 47 reviews
21 repeat clients
5 years of experience
Woodlawn, Chicago, IL, 60637

“Dominique is very reliable, Friendly and Flexible to my schedule. Trustworthy, and cares about my Fur Babies. She also took very cute pictures of my kitty Simba and my Dutch Shepherd Shana.”

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Terese C.
Sitter Profile Image: Erin M.
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Erin M.
from
$20
per visit
5.0 out of 5 stars
• 22 reviews
10 repeat clients
2 years of experience
Hyde Park, Chicago, IL, 60637

“Erin was a great help for us on short notice. She was promptly communicative, reliably on time, followed instructions perfectly, and most importantly treated my bunny with care and affection. Thank you Erin!”

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Alexis M.
Sitter Profile Image: Jasmine P.
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Jasmine P.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
• 100 reviews
39 repeat clients
10 years of experience
Kenwood, Chicago, IL, 60615

“Jasmine was amazing! They followed instructions, asked questions and gave a thorough summary of what happened each day! Greatly appreciate the thoughtfulness and care put into the time spent with my furry friend. Much appreciated!!”

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Jon P.
Sitter Profile Image: Camryn A.
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Camryn A.
from
$20
per visit
5 years of experience
Chicago, IL, 60637

About: I’ve had my maltipoo since 2020 and have taken care of dogs since then as well. I’m very organized and attentive to your animals needs! I just moved to Chicago so i have a lot of free time especially during the summer while i look for other jobs. I love having new energy around me at all times :) I have a very safe apartment complex with an enclosed backyard. Lots of toys for them as well to make them feel comfortable! I’m attentive and a very good listener to all of their needs

Sitter Profile Image: Taylor W.
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Taylor W.
from
$20
per visit
5.0 out of 5 stars
• 5 reviews
2 repeat clients
17 years of experience
Chicago, IL, 60615

“Great! No complaints. Will be scheduling again soon. My cats loved her and she followed instructions exactly.”

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Chevonne C.
Sitter Profile Image: Byron G.
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Byron G.
from
$17
per visit
20 years of experience
South Shore, Chicago, IL, 60649

About: I Love animals. Especially dogs and cats. I have over 20 years of experience caring for dogs and cats of all kind. Your pet will be staying in my home, so they will have the whole house to themselves. I take extra long walks to the park and the beach often. You will never find anyone more invested in your best friend. Every hour of every day is dedicated to caring for your best friend. I am very active. I go to the gym 5 days a week. Working with dogs and cats gives me what we need in order to stay fit and mental stable. I will have your doggies tired at the end of the day!! The doggies and kitties have the entire house to their self. I have a big home with 4 floors. I also have a large yard that is fenced in and totally secure. No one gets in or out unless I decide to.

Sitter Profile Image: Kiera B.
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Kiera B.
from
$25
per visit
5.0 out of 5 stars
• 30 reviews
22 repeat clients
8 years of experience
Chicago, IL, 60615

“Amazing as always! Sorry, yes Sookie got new bowls from his grandma for Christmas. Thank you so much for taking care of my boy :)”

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Sarah S.
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The median cost per visit for pet sitting in Woodlawn is $20

Pet parents share their Rover experiences - Woodlawn

1 / 1
5.0 out of 5 stars

Emily is amazing!! She’s great with our cat, super responsive and communicative, and did a great job taking care of our cat overall.

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Genevieve A.
Drop-In Visits
5.0 out of 5 stars

Cathalina was perfect, did daily check ins while I was out of town ! Sent pictures to update us everyday while I was away missing my pup! 10/10 would rebook cathalina again !!

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Areanna M.
Drop-In Visits
5.0 out of 5 stars

Ashley is amazing! She takes excellent care of our dog Argo and is very communicative. We really appreciate her help!

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Tiffany A S.
Drop-In Visits
5.0 out of 5 stars

Qutress went above and beyond for my dogs. Very communicative, and I felt my dogs were well taken care of.

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Emily P.
Drop-In Visits
5.0 out of 5 stars

What an amazing pet sitter! Our dog can be a bit nervous with people, but he absolutely LOVES Nicole. She came ready with treats too, so they were best friends pretty fast. Will be rebooking with her for sure!

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Faith S.
Drop-In Visits
5.0 out of 5 stars

Coretta is an absolute pro with fur babies! She is extremely timely and a great communicator. I look forward to booking with her again!

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Lauryn T.
Drop-In Visits
5.0 out of 5 stars

Communicative and patient! We have an anti-social and sometimes aggressive cat and Victoria handled her with patience and understanding. Will definitely rebook in the future.

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Peter B.
Drop-In Visits
5.0 out of 5 stars

Thank you Syenna! Syenna is great to work with. Communicative, great with our Alusky! Happy to have found her.

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Tanarra S.
Drop-In Visits
5.0 out of 5 stars

Christina was great. She was communicative, on time, and showed my cat lots of love. This was my first time leaving her and I was nervous but there was absolutely nothing to worry about. Christina was on top of it. Will be using her again

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Jaymi G.
Drop-In Visits
5.0 out of 5 stars

Cassandra took such good care of our two cats. She followed all of our instructions and sent lots of pictures and detailed updates on how they were doing. She is also very prompt in answering texts. Highly recommend.

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Meredith M.
Drop-In Visits
5.0 out of 5 stars

Haley watched our cat, Leo, for a long weekend. She was incredibly responsive and communicative, which we appreciated!

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Anna B.
Drop-In Visits
5.0 out of 5 stars

Jasmine was great, I really appreciated her willingness to come over for a meet and greet before sitting. Thanks for letting Mickey lick the spoon! 🐈😹

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Danielle W.
Drop-In Visits
5.0 out of 5 stars

Grace was great! I received photos of her visits and notifications when she arrived and left. She brushed and played with Ollie while here. My worry was assuaged knowing that Ollie was in good hands with Grace. I will definitely reach out to her again.

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Julie H.
Drop-In Visits
5.0 out of 5 stars

lucille is amazing wonderful spectacular etc etc etc!!!! so kind and sweet and considerate with my two sweet babies. also provides so many fun pictures and comments! strong recommend 💟😸

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Via M.
Drop-In Visits
5.0 out of 5 stars

The best summaries I’ve ever received from a pet sitter here on Rover. Will definitely book again with Huibo in the future!!

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Dominique L.
Drop-In Visits
5.0 out of 5 stars

Che was awesome! Incredible energy and friendliness with my cat. Very proactive and responsible with the reports and pictures - I would definitely book again.

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Daniela C.
Drop-In Visits
5.0 out of 5 stars

Thank you so much for taking such great care of our cats while we were gone! All the photos were lovely to see on our trip, and I can tell they were taken care of very well. Would definitely book you again for our next trip. Thanks again!

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Zinnia R.
Drop-In Visits
5.0 out of 5 stars

Amiyah did an incredible job taking care of Wraith, making sure she ate food, drank water, and played during the time I was away. She is great with sending photos and communicating and I would definitely recommend her!!

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Joshua K.
Drop-In Visits
5.0 out of 5 stars

Julia has exceeded my expectations with my fur baby, Lilo. I appreciated all the photos that showed consistency in love and affection, and even offering to swing by and check on Lilo on off days. 10/10 recommend! 100% will rebook Julia in the future.

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Christopher S.
Drop-In Visits
5.0 out of 5 stars

Working with Lyn is always a breeze! We feel so calm leaving our cat with her & always look forward to the pictures and detailed check ins.

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Heather W.
Drop-In Visits
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Sitters in Woodlawn average 6
repeat pet sitting clients

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