Pet Sitting & Drop Ins In Kenwood

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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Top rated Kenwood pet sitters

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

Evan was very communicative and easy to work with.

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Jill Y.
Sitter Profile Image: Qutress T.
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Qutress T.
Star Sitter
from
$17
per visit
5.0 out of 5 stars
81 reviews
31 repeat clients
10 years of experience
Grand Boulevard, Chicago, IL, 60615

Q has quickly become our go-to pet sitter. She always provides top-notch care, and we love that she is often accompanied by her son, who our cat absolutely adores.

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Connor R.
Sitter Profile Image: Amiyah W.
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Amiyah W.
from
$14
per visit
1 repeat client
10 years of experience
Grand Boulevard, Chicago, IL, 60615

About: I've had pets since I was 9. From 9 till now I've had cats, dogs, fishes, and guinea pigs. I have experience with dealing with pets that may have previously trauma issues also with pets that may need careful care like medince or special needs. Even pets that don't need extra care just pets that wants to have long walks or need a lot of play time . I am currently in school. So I will be working part time for Rover. Evening and nights works best for the weekdays and for the weekends I am open for anytime you need. For cats do have multiple cat bags if they need to brought to a appointment or any where else. And foot dogs if you don't have a leach I can get one but I would prefer for you to have leeches and rates of pets need to be taken out of the house .

Sitter Profile Image: Maya C.
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Maya C.
Star Sitter
from
$22
per visit
5.0 out of 5 stars
110 reviews
44 repeat clients
8 years of experience
Chicago, IL, 60615

Maya is the best! I book with her all the time because not only is she reliable and dependable but she puts my mind at ease. Sierra is in great hands with her

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Albina K.
Sitter Profile Image: Jasmine P.
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Jasmine P.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
97 reviews
38 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: Christina D.
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Christina D.
Star Sitter
from
$10
per visit
5.0 out of 5 stars
5 reviews
3 repeat clients
13 years of experience
Oakland, Chicago, IL, 60653

I am so happy that I found Christina to take care of my little Rainbow while I was away! She was very caring and they bonded like love at first sight for our meet and greet. It shows that Christina really loves cats and went out of her way to make sure that mine was comfortable and happy! When I came home, everything was neat and clean and Rainbow was happy and ready to play as if I had never left! I would highly recommend Christina and book her again, thank you so much!

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Tracee H.
Sitter Profile Image: Deanna L.
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Deanna L.
from
$15
per visit
5.0 out of 5 stars
12 reviews
2 repeat clients
2 years of experience
Kenwood, Chicago, IL, 60615

About: I treat every pet like family, patient, observant, and caring. I may be new, but I come with love, responsibility, and a pocket of treats Working full time with reduced summer hours, plus weekends & holidays off, I’m available to offer consistent, caring attention and companionship for your pets! :) Pets in my care have access to walking paths, a dog park, a wash station, and designated potty areas. Crate-trained pups are welcome! I keep communication clear because guessing games are for pets, not pet parents

Sitter Profile Image: Taylor W.
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Taylor W.
from
$20
per visit
5.0 out of 5 stars
4 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: Brianna B.
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Brianna B.
from
$10
per visit
5.0 out of 5 stars
5 reviews
4 years of experience
Hyde Park, Chicago, IL, 60615

About: What sets me apart is my lifelong, hands-on experience with animals of all kinds. I grew up on a farm in Idaho caring for dogs, cats, chickens, goats, ducks, reptiles, small pets like mice and hamsters, and even birds—so I’m comfortable with a wide range of needs and personalities. I also have extensive experience with dogs, from helping our Great Pyrenees have a litter of puppies to raising around 8 dogs from 6 weeks old into adulthood. I’m especially confident with puppy care, early training, and building routines. I love working with puppies, but I’m just as experienced with senior dogs and those who need extra attention. I’ve cared for pets with special diets, medications, and potty needs, always with patience and consistency. As a kindergarten teacher, I bring structure, attentiveness, and a calm, caring approach—your pet will be treated like family. During the summer, I have a very open and flexible schedule since I’m not teaching kindergarten. This allows me to fully prioritize pet care, including walks, drop-ins, and extended visits throughout the day. I’m used to maintaining structured routines, so I’m happy to follow your pet’s specific schedule for feeding, walks, playtime, and any special care needs. Pet care fits easily into my daily routine, and I enjoy spending my time staying active and outdoors—especially with dogs! I always tailor my care to each pet’s specific needs and routine. In a client’s home, I aim to keep pets comfortable by maintaining their normal schedule for feeding, walks, playtime, and rest. I make sure they get plenty of attention, exercise, and affection, while also keeping their environment clean and safe. In my home, pets are treated like family. I have two Yorkies of my own who are extremely friendly, well-trained, crate trained, quiet, and great with kids. I’m very used to providing consistent care, supervision, and a calm, structured environment with regular walks and play. I’m also mindful of each dog’s personality, energy level, and any special needs like medications, diet, or potty routines. No matter the setting, my goal is to make pets feel secure, loved, and well cared for while you’re away.

Sitter Profile Image: Lucille C.
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Lucille C.
Star Sitter
from
$25
per visit
4.9 out of 5 stars
17 reviews
2 repeat clients
5 years of experience
Chicago, IL, 60615

Lucille is excellent with our dog Kaia. We thank her for spending time showering her with belly rubs and attention. Looking forward to more visits with her.

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NORMA L.
Sitter Profile Image: Rahmya T.
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Rahmya T.
from
$16
per visit
6 years of experience
Hyde Park, Chicago, IL, 60615

About: Hii! I’ve had at least 2 pets my whole life; cats, dogs, and even a ferret! I currently have 2 young cats that I absolutely adore. I’ve been dedicated to understanding animal behavior to make them as happy as possible. My best friend is a vet nurse, so there’s always a doctor on call! I’m a freelance photographer, so as long as I have my laptop and wifi, I can typically work anytime from anywhere. Unavailability otherwise noted in calendar Knowing your pet is best! I know our furry friends get mischievous when they’re bored, lots of playtime and mentally stimulating toys are key! And of course lots of treats and love

Sitter Profile Image: Cassandra H.
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Cassandra H.
from
$15
per visit
5.0 out of 5 stars
69 reviews
25 repeat clients
15 years of experience
Hyde Park, Chicago, IL, 60615

Cassie is amazing at what she does and she is very professional and warm. She took great care of our cat and our home. She was always punctual and always sent wonderful notes and pictures. We would happily choose her again to take care of our cat.

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Sud R.
Sitter Profile Image: Mia L.
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Mia L.
from
$20
per visit
5.0 out of 5 stars
26 reviews
5 repeat clients
7 years of experience
Hyde Park, Chicago, IL, 60615

Mia was personable and professional from our very first text. After her initial visit, I felt completely comfortable leaving my cat in her hands. I was able to relax while away and come home to a healthy, happy cat!

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Teresa R.
Sitter Profile Image: Cassandra B.
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Cassandra B.
from
$25
per visit
5.0 out of 5 stars
8 reviews
2 repeat clients
11 years of experience
Kenwood, Chicago, IL, 60615

Thanks again for over caring for the dogs and stray kitty! My return home to them was like returning from work. (Even tho it was days) They were happy but not overly excited to see me and I know that is nothing short of you giving them the opportunity for their routine to not be disturbed and visiting with them with love!

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Heather B.
Sitter Profile Image: Ashleigh P.
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Ashleigh P.
from
$19
per visit
5.0 out of 5 stars
52 reviews
18 repeat clients
15 years of experience
Hyde Park, Chicago, IL, 60615

Ashleigh always does a great job and sends detailed updates. It’s always a relief to know Ashleigh will have everything taken care of back at home.

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Lauren P.
Sitter Profile Image: Jessy M.
Verified Enhanced Background Check
Jessy M.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
15 reviews
6 repeat clients
13 years of experience
Hyde Park, Chicago, IL, 60615

Jessy was very responsive and did everything I asked of her!

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Leah C.
Sitter Profile Image: Simone B.
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Simone B.
from
$25
per visit
5.0 out of 5 stars
10 reviews
3 repeat clients
23 years of experience
Chicago, IL, 60615

Simone is absolutely amazing! She did a drop in before our first visit, which we know is extra work and she didn’t mind at all to take care of our sweet puppy who’s 4 months old. She didn’t mind the zoomies and I’m sure was so patient and playful with our pup we are absolutely booking a drop in again!

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Dana W.
Sitter Profile Image: Ava M.
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Ava M.
from
$20
per visit
5.0 out of 5 stars
7 reviews
3 repeat clients
11 years of experience
Hyde Park, Chicago, IL, 60637

Ava went above and beyond watching my 3-year old golden. She clearly loves dogs and loves her job. Would be happy to book with again.

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Jada D.
Sitter Profile Image: Chelsea G.
Verified Enhanced Background Check
Chelsea G.
Star Sitter
from
$26
per visit
5.0 out of 5 stars
38 reviews
12 repeat clients
20 years of experience
Douglas, Chicago, IL, 60653

Chelsea was a fantastic rover for our dog! She was extremely responsive, punctual, and helped us several times on short notice! She also clearly cared for our dog and was super kind. Would recommend her to anyone!

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Libby R.
Sitter Profile Image: Huibo L.
Verified Enhanced Background Check
Huibo L.
from
$15
per visit
10 years of experience
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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Kenwood pet parents share their Rover experiences

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5.0 out of 5 stars

Coretta is an outstanding, capable individual! She knows how to care for cats and dogs very well. She is great communicating with people, including building supervisors, managers and maintenance workers. Coretta is flexible in scheduling and diligent in her attention to detail. When asked for special considerations, she will go above and beyond to make sure animals entrusted to her care ware well fed, clean and loved! I will absolutely go out of my way to employ her services again, should the need arise. If you have the opportunity to work with Coretta, or have her visit your home, you'll be all the better for it! She is an absolute PROFESSIONAL!

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

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.
Drop-In Visits
5.0 out of 5 stars

Daphnay was awesome with Zena. She followed all of our instructions for Drop-in visits, sent reports and updates after each visit. We'd definitely book with her again. Thanks so much again, Daphnay!

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Chent & Princess S.
Drop-In Visits
5.0 out of 5 stars

Called before to establish clear, detailed communication for her checklist. Walked my dog and sent update videos/pictures as she completed her checklist throughout the service.

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Jonte' W.
Drop-In Visits
5.0 out of 5 stars

Bri was responsive and super friendly with our kitty crew! She accommodated us on short notice thankfully and though our cats were hot and cold with her (typical of felines) she was patient and calm with them. Would definitely book again!

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

Rachel was great! We loved having her take care of the girls again and would 1000% book with her again!

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Payton D.
Drop-In Visits
5.0 out of 5 stars

Joselin was so kind and responsive. He took care of my sweet baby cat for two days very well. She is so communicative! She sent a lot of photos and videos of my cat. Highly recommended.

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

Nikki was so great!! Spent a good amount of time with my cats and they seemed so happy when I got back.

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Katie D.
Drop-In Visits
5.0 out of 5 stars

I was delighted that Maya could help us, when we planned an out of town trip on fairly short notice. She has taken care of our cats in the past, so we knew we were leaving Casey in good hands. Maya sent us regular reports and cute pictures, and Casey was very mellow when we got home. 5 star care!

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

Thank you so much for caring for my babies! I appreciate it! highly recommend for all your pet booking needs!

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

I am so happy that I found Christina to take care of my little Rainbow while I was away! She was very caring and they bonded like love at first sight for our meet and greet. It shows that Christina really loves cats and went out of her way to make sure that mine was comfortable and happy! When I came home, everything was neat and clean and Rainbow was happy and ready to play as if I had never left! I would highly recommend Christina and book her again, thank you so much!

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

Lucille is definitely a kind soul and I appreciate her help walking my best friend. I would highly recommend and book again ☺️

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

Thank you for taking care of Kaia. It seemed like our dog had a great time with her doing a brief walk and some cuddle time. We definitely recommend Annie and looks forward to using her services again.

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

We’re so lucky to have found Jasmine! I have a very territorial cat but her calm demeanor and patience paid off and he got comfortable with her presence.

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

Allison was great with our dog. She was super understanding and open to our dog’s timeline and comfort level. Definitely recommend!

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Autumn D.
Drop-In Visits
5.0 out of 5 stars

Lynettra is very reliable and takes care of cat very well! Grateful to have her as a sitter for him!

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

Cassie is an excellent cat sitter. She took care of my cat while going through some medical stuff, and took the time to make sure her medication was administered correctly and with care, and also to help reassure and update me while I was away. I really appreciate it!

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

I'm a repeat client! Madison is great with my Bernedoodle, he loves when she takes him for walks. She's also prompt and communicates effectively.

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

Megan took care of our cat regularly for two weeks, and we couldn’t be happier with her help. Our cat has a very sassy and cautious personality, but Megan managed to win her over, which honestly says a lot. She was able to pet her and even got her to play, which is not easy at all. We are very grateful to Megan for her care, patience, and reliability. It gave us great peace of mind knowing our cat was in such good hands. We would absolutely recommend her to anyone looking for a caring and trustworthy pet sitter.

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

Claire is absolutely wonderful. She accepted my request at the last minute and truly cared about my cats’ well-being. She kept me updated throughout the day and made me feel completely at ease. She’s definitely a keeper, and I would highly recommend her to anyone

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Teslyn B.
Drop-In Visits
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Pet Sitting FAQs

Frequently asked questions about Rover

If you’re searching for a Kenwood pet sitter for the first time, visit the pet sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a pet sitter before, learn more about how to do this in the Rover app or on your computer.

Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, pet sitters on Rover respond in under an hour.

Experience can vary widely from pet sitter to pet sitter, but you can view reviews, years of experience, and number of repeat clients when comparing pet sitters available in Kenwood.

Rover makes it easy to find Kenwood pet sitters to provide loving care from their own home. The background-checked, 5-star pet sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet sitting is great for:

  • Pets of all ages and abilities, including puppies
  • Pet parents looking for a safe, loving alternative to a kennel
  • Pets who’d love to socialize with their pet sitter’s pets

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your pet sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your pet sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your pet sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your pet service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.