Pet Sitting Kenwood

“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.”

NORMA L.

“Thank you so much!”

Catherine G.

“Chelsea was very punctual, provided lots of updates and pictures, communicated well, and poppy loved her! We will definitely be using her again and I 10/10 recommend her!”

Freddie V.

“Cassandra listens and is trustworthy. We spoke for awhile exchanging dog (pet watching) experiences and I knew I could trust her with my dogs and my home: Her visit consisted of having lockbox access to our house, access to the dogs and returning everything as requested.”

Heather B.

About: Transparently I am largely new to pet care! I did spend one summer, while staying with a friend’s family for an out of state internship, taking care of a big dog, Ryker, & old cat, Opi & I thoroughly enjoyed the routine! I would feed them both, run with Ryker, take him out for bathroom breaks, & bathe him too! However, I am currently home full time & can accommodate your fur babies’ needs! Whether that be long walks at the park, playing fetch for forever, or anything else needed to ensure their comfort! I am currently new to the area & I am completely free until my grad program begins! Staying active near the park, building routine, & getting to know my community allows pet care to fit perfectly into my daily & weekly routine ! I am in an apartment so I am more suitable for daytime walking or check ins, but can house a pet if needed! I would ensure our space is suitable for them!

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

Chevonne C.

About: As a big sister and true animal lover, I have delighted in taking responsibility and caring for the children and fur-babies of family, friends, and neighbors for most of my life. My experience with dogs and cats is extensive, including: extended periods of 24/7 care for varying ages, sizes, and needs; following veterinary instructions for administering medications; and providing proper everyday care such as bathing, feeding, walking, and basic grooming, and of course plenty of play-time and snuggles! For walks and check-ins I am flexibly available on Saturdays and Sundays, and during the week I am available Tuesdays 3pm - 6pm, Wednesdays 8am - 11am, and Fridays 1pm - 6pm. I am also able to provide overnight/multiday care at my home for cat-friendly pets. My apartment is a spacious 3 bed/2 bath (I have 3 couches to choose from for naptime and snuggles!), with plenty of parks, trails and green spaces nearby to walk and play. I have a sweet kitty at home who loves to play with other cats, and dogs too! Some things to keep in mind when deciding if my home is right for your fur-baby's stay: I live on the 2nd floor and my building does not have an elevator; if your pet uses a crate you will need to provide this for their stay; I have a cat and so will only be able to welcome cat-friendly pets to my home.

About: Hi! I’ve cared for dogs and cats of all sizes, temperaments, and energy levels for most of my life. I’ve had dogs my entire life and cats of my own for 10 years, and I began pet sitting at 16. I’m comfortable with active and senior pets, structured routines, and medication administration. I follow instructions closely, provide reliable updates, and keep clients’ homes clean and secure. I’m currently taking a planned career sabbatical while attending school and pursuing professional development. I welcome one-time and recurring walks, drop-ins, and house sits. . Beginning August 20, I have class Tuesdays and Thursdays. On these days, I can provide early-morning and late-afternoon or evening care but will be away during normal working hours. I may also have evening commitments or part-time service shifts. . I keep my calendar current and confirm exact availability before booking. I expect clients to clearly communicate their requested schedule and services. . SERVICE AREA I’m based in Hyde Park and primarily serve clients within roughly two miles of my home—generally no more than a 20-minute bike ride. I may accept requests outside this area for an additional travel fee. . I expect to relocate closer to the Loop or Medical District in late September or early October. I welcome recurring arrangements now, including inquiries from clients near my anticipated future service area. Availability and travel pricing for care continuing after my move will be reconfirmed once my new address is finalized. . PRICING Listed rates reflect standard care. Custom pricing may apply for medication administration, medical monitoring, extended in-home presence, significant travel, or other care beyond my standard services. Any adjustment will be discussed and confirmed through Rover before booking. . CANCELLATIONS Bookings are subject to my seven-day cancellation policy. Please notify me promptly if your plans change. House sitting includes overnight care. Standard house sitting does not include continuous or 24-hour presence; pets must be able to remain safely alone during agreed timeframes. I leave as needed to care for my own cat and attend class or other scheduled obligations. . Drop-ins and walks are provided for the booked 30 or 60 minutes. Requested care must reasonably fit within that time; clients with more involved routines should book 60 minutes. . Walks are paced to each dog’s age, health, energy, and training using client-provided equipment and instructions regarding routes, commands, and reactivity. . For all services, I follow entry and alarm instructions, confirm that pets and the home are secure before leaving, and provide an update after each visit.

“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!”

Tracee H.

“Amiyah is kind and caring.Glitzy had lots of fun and looked forward to her visits with Amiyah. We felt she was very well cared for and that makes vacationing easier..”

Turqueya W.

“Jasmine R was awesome. Thorough and punctual. My kitty was happy and my home was just as I left it. I will use her services again.”

Stacey S.

“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.”

Anna B.

“Qutress was great with our shy cat, who even let Qutress pet her which is quite rare for newcomers! She was very communicative and gave us wonderful updates every day. Highly recommend!”

Luke M.

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!

“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!!”

Jon P.

“It was my first time using rover and I was looking for someone who truly understands dogs, and its Tamara! Tamara was a true blessing while I was away in Mexico. My dog isn’t usually quick to trust—he even tried to bite her when they first met—but she was so patient and kind with him. By the end of the week, he was waiting at the door for her, tail wagging, 30 minutes early. I could tell he really bonded with her. I’m so grateful and would absolutely have her watch him again.”

Al T.

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!

About: What sets me apart is my focus on individualized care for each pet. I take time to understand their routine, personality, and comfort needs so they feel safe and relaxed while you're away. I’m reliable, attentive, and make communication a priority by providing regular updates with photos and messages. Pet care fits easily into my daily routine because I have a flexible and organized schedule that allows me to prioritize visits, feedings, and check-ins consistently. I’m able to plan my day around morning, afternoon, and evening care as needed, making sure pets receive attention on time and without rush. I’m also good at managing responsibilities, so I can balance pet care with other commitments while still being reliable and responsive. Whether it’s drop-ins, feeding, playtime, or house sitting, I can adapt my routine to meet each pet’s needs and ensure they stay comfortable and well cared for throughout the day. I provide care for pets in their own home to help keep them comfortable in their familiar environment. I offer house sitting, where I stay in the home as needed to provide companionship, maintain routines, and make sure pets are fed, walked, and well cared for. I also offer dog walking and daily walks to ensure pets get regular exercise, bathroom breaks, and attention throughout the day. In addition, I can handle scheduled feedings and basic care routines exactly as instructed by the owner. I do want to note that I do not offer boarding or training services. My focus is on in-home care and walking services, making sure pets stay safe, relaxed, and well looked after while their owners are away or busy.

“Che was friendly, helpful, and reliable. Cats can’t wait to see her again.”

Daniel R.

“Jessy did a great job taking care of our pets while we were away! Very responsive and caring! Thanks Jessy!”

Mariel H.