Pet Sitting & Drop Ins in Kenwood, Chicago
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
“Abi communicates well and attends to the needs of our dogs. I appreciate that she alerted me to a new open lesion on Eiko’s front leg. By taking pics of the affected area- we were able to address the issue as soon as we saw the wound. Much thanks!!!🙏🏼”
“Tamara has been a wonderful support to our family. She’s a quick learner, is patient and communicates well. Our team pups enjoy her and always look forward to their walks with her.”
“Qutress was so considerate, sweet, and caring with our kitty cat and we would absolutely love to book her again!! She did everything we needed to a T and sent us lots of helpful updates and cute photos too! We felt really happy and relieved as anxious pet parents knowing that Qutress was nearby and available to help with drop ins while we were out of town :)”
“Dana is amazing! She was so helpful and cared for our 2 kitties like they were her own. She stopped by to see where their things were and meet them before the drop-ins. Thank you, Dana!”
“Great with dogs! Daphne gave our 11yr old and 1yr old so much love and attention during her mid day drop in visits, we are grateful for her service. Wonderful and easy to work with and we will definitely use again.”
“Samantha is such a great sitter! She’s super communicative and sends great updates during her visits. It definitely makes traveling/having to leave my cat much easier knowing that she will be in Samantha’s care ☺️”
“Sanaa was a great sitter for my cat! She responded so quickly to my messages and did everything perfectly for the drop-in visit. I’ll for sure be contacting her next time I need a sitter!”
About: With years of experience, I provide top-notch pet care that's reliable, loving, and personalized. Your furry friend will feel safe, happy, and well-cared-for. Book Now! Working from home allows me to dedicate ample time to caring for my dog and yours. I ensure a calm, focused environment where it’s just our two fur babies, receiving all the love and attention they deserve. I have a fenced yard, perfect for pups to play and explore safely. My miniature Labradoodle, Jax, loves having company, and we have plenty of treats and toys to keep your dog happy and entertained!
About: I have been petsitting almost my entire life and absolutely love spending time with cats and dogs! Throughout my life, friends and neighbors often asked me to pet-sit and I developed lots of experience understanding pets and their unique personalities. I have also cared for several senior pets and have experience administering medications (liquid and pill). Reliability, communication, and thoughtful care are always my top priorities! I am a graduate student at U Chicago studying for my master’s in social work. This summer I have a part-time internship and my hours are very flexible. I have availability any day of the week! I will make sure to follow any and all instructions so that your pet is cared for and safe! From experience, I am good as sensing when a cat or dog might need some space or more attention. I am an attentive, thoughtful, and communicative pet-sitter.
About: I’ve grown up with dogs—big and small!—my entire life, and I’ve missed interacting with them since I’ve moved to Illinois. I have extensive experience caring for the pets of family and friends, and pet safety is my #1 priority! I’m currently a student working remotely, so I have time most weekdays and weekends to spend time with your pups and/or take them on walks! I am very conscientious of the environment when handling pets in and out of the home. It’s important to me that pets are secure when on walks or in their home. I’m comfortable crating dogs when desired and double checking any doors, fences, and/or leashes, depending on the setting.
“Thank you for a great job!”
“Peyton has made returning to the office so much less stressful. She is wonderful with my under-socialized dogs and has given me true peace of mind.”
About: I’ve taken care of dogs and cats on and off. Although, I’ve yet to learn more about pet care, I know with my background in mental health for 8 years that I value listening to what people value and supporting them in maintaining their values. So, I see myself listening to you, learning from you, and supporting in managing any anxiety you might have about a complete stranger taking care of your pet. I’ve walked dogs, played with cats, and cleaned up after dogs, and cleaned up after cats. I know it’s hard work ( with my limited experience) and I want to support. Please ask me any questions or voice any concerns you might have. Open to a conversation. My schedule in this moment consists of weekends only with Saturday and Sunday being the days that I’m available. This is to help me maintain the self-care needed to engage in my role effectively. I’m happy to learn and review the uniques necessities and care you need for your pet. I’m happy to and have experience walking dogs, cleaning up after cats, playing with cats, and cleaning up after dogs as well,
“Bola’s wonderful! We’re glad to have her support with our dogs.”
“Madison did great in taking care of our cat. Sometimes she can be a picky kitty and makes a mess, but Madison cleaned up after her, cuddled with her and made sure to be in as much (or as little) communication as I requested. She sent pictures which assured us the cat was well taken care of, and overall was a joy to work with. We will definitely be rebooking her!”
About: I had five dogs since the age of seven, and it was my responsibility to feed, bathe, walk, and play with them. I enjoyed caring for them so much that when I turned eight, I began walking and checking on my neighbor’s dogs, making sure they were fed and had potty breaks. By the time I was 16 and could drive, I began house and pet sitting for family friends. I continued to house and animal sit, as well as dog walk, throughout college and widened my network beyond just friends. I love getting to know new pets, learning their personalities and earning their trust. Pets are a part of your family and deserve love and care from someone you can trust. I hope you will let me earn that trust and get to know your furry family! I work remotely from home so my schedule is flexible. Which allows me to take time to care for your pets whenever needed. You do not have to worry while you are gone that I will not be able to care for your pets because of a time constraint due to work. I can be there when needed to walk, play, or feed them. If you need me to housesit, rest assured that I can work remotely from your home as well, ensuring that your furry family member is not alone and cared for. Entrusting your pet and your home to someone is a big decision and I do not take that responsibility lightly. I pride myself on treating your pet and private space with the utmost respect. If there are specific requirements that your pet needs, dietary, grooming, or communication, you can be assured that I will follow them to the letter. Respect and trust are something that is earned, and I hope that you will give me the chance to show you how much I care about making animals comfortable and happy, as well as putting owners at a peace of mind knowing their animals are taken care of.
About: Hello! I grew up with my German Shepard mix, Remus, who was my sidekick for 8 years. I now have Anya, a pit mix from Baltimore, who has been my sidekick for 5 years. I have lots of experience walking, giving pets meds, and checking in for food and treats and playtime. I have spent time with and walked loads of different types of dogs. Every dog is unique and I am excited to make friends with yours! I work full time at University of Chicago but keep fairly flexible hours. I can drop in before and after work and check in late at night as well in the Hyde Park area. I can walk your dog and give treats according to your instructions. I can also drop in to give meds or food and let your dog out, depending upon your and your dog’s needs. I am comfortable with small and big dogs.
“Madison was absolutely wonderful, I can’t recommend her enough. I have a senior cat with some extra medical needs and she was incredibly patient and kind in taking care of him. I felt at ease knowing my kitty was in good hands with her!”
About: Having grown up with animals and volunteered at the humane society, I have experience caring for a variety of canine and feline creatures, including those who need medication, training, and late-in-life care. I love enhancing a dog’s quality of life whenever I can by providing individualized care. I also really enjoy walking and grooming. I am looking to transition into full-time animal care, so my schedule is very flexible. Please do not hesitate to reach out with any questions! I have a sweet four-year-old kitty named Minky. She is great with other animals (especially cats), and is very calm. If your pet is not comfortable with other animals or cats, I am happy to watch them at your place instead of boarding.
Loving pet sitters in your neighborhood
Search Results
1. Abi S.
“Abi communicates well and attends to the needs of our dogs. I appreciate that she alerted me to a new open lesion on Eiko’s front leg. By taking pics of the affected area- we were able to address the issue as soon as we saw the wound. Much thanks!!!🙏🏼”
2. Tamara J.
“Tamara has been a wonderful support to our family. She’s a quick learner, is patient and communicates well. Our team pups enjoy her and always look forward to their walks with her.”
3. Qutress T.
“Qutress was so considerate, sweet, and caring with our kitty cat and we would absolutely love to book her again!! She did everything we needed to a T and sent us lots of helpful updates and cute photos too! We felt really happy and relieved as anxious pet parents knowing that Qutress was nearby and available to help with drop ins while we were out of town :)”
4. Dana J.
“Dana is amazing! She was so helpful and cared for our 2 kitties like they were her own. She stopped by to see where their things were and meet them before the drop-ins. Thank you, Dana!”
5. Daphnay S.
“Great with dogs! Daphne gave our 11yr old and 1yr old so much love and attention during her mid day drop in visits, we are grateful for her service. Wonderful and easy to work with and we will definitely use again.”
6. Samantha E.
“Samantha is such a great sitter! She’s super communicative and sends great updates during her visits. It definitely makes traveling/having to leave my cat much easier knowing that she will be in Samantha’s care ☺️”
7. Sanaa A.
“Sanaa was a great sitter for my cat! She responded so quickly to my messages and did everything perfectly for the drop-in visit. I’ll for sure be contacting her next time I need a sitter!”
8. Kelsie G.
“Kelsie is an amazing dog sitter. Kelsie has kept my dog multiple times and the longest was 2 weeks. Kelsie would send pictures/videos daily and provided updates. Kelsie was willing to meet me and my dog beforehand to ensure that my dog would be comfortable with her and he was! I will definitely use Kelsie again.”
9. Molly G.
“No one is as caring and loving towards animals as Molly! She is responsible in routine feeding, providing bathroom care, and pet attention. As someone who has known Molly from childhood to adulthood, I can say with certainty that she has always been an animal lover and is very responsible.”
10. Megan T.
About: I’ve grown up with dogs—big and small!—my entire life, and I’ve missed interacting with them since I’ve moved to Illinois. I have extensive experience caring for the pets of family and friends, and pet safety is my #1 priority! I’m currently a student working remotely, so I have time most weekdays and weekends to spend time with your pups and/or take them on walks! I am very conscientious of the environment when handling pets in and out of the home. It’s important to me that pets are secure when on walks or in their home. I’m comfortable crating dogs when desired and double checking any doors, fences, and/or leashes, depending on the setting.
11. Brianna J.
“Thank you for a great job!”
12. Peyton W.
“Peyton has made returning to the office so much less stressful. She is wonderful with my under-socialized dogs and has given me true peace of mind.”
13. Ryan F.
“Ryan met my pup Mifflin, a 70 pound pit mix, a couple of years ago and they have been best buds ever since! Ryan did not shy away from his size or breed and instead connected with Mifflin on his love for cuddling and playing fetch. I appreciate Ryan’s openness to larger dogs and know that when Mifflin is with Ryan, he is in great hands.”
14. Bola A.
“Bola’s wonderful! We’re glad to have her support with our dogs.”
15. Madison M.
“Madison did great in taking care of our cat. Sometimes she can be a picky kitty and makes a mess, but Madison cleaned up after her, cuddled with her and made sure to be in as much (or as little) communication as I requested. She sent pictures which assured us the cat was well taken care of, and overall was a joy to work with. We will definitely be rebooking her!”
16. Timothy M.
About: I had five dogs since the age of seven, and it was my responsibility to feed, bathe, walk, and play with them. I enjoyed caring for them so much that when I turned eight, I began walking and checking on my neighbor’s dogs, making sure they were fed and had potty breaks. By the time I was 16 and could drive, I began house and pet sitting for family friends. I continued to house and animal sit, as well as dog walk, throughout college and widened my network beyond just friends. I love getting to know new pets, learning their personalities and earning their trust. Pets are a part of your family and deserve love and care from someone you can trust. I hope you will let me earn that trust and get to know your furry family! I work remotely from home so my schedule is flexible. Which allows me to take time to care for your pets whenever needed. You do not have to worry while you are gone that I will not be able to care for your pets because of a time constraint due to work. I can be there when needed to walk, play, or feed them. If you need me to housesit, rest assured that I can work remotely from your home as well, ensuring that your furry family member is not alone and cared for. Entrusting your pet and your home to someone is a big decision and I do not take that responsibility lightly. I pride myself on treating your pet and private space with the utmost respect. If there are specific requirements that your pet needs, dietary, grooming, or communication, you can be assured that I will follow them to the letter. Respect and trust are something that is earned, and I hope that you will give me the chance to show you how much I care about making animals comfortable and happy, as well as putting owners at a peace of mind knowing their animals are taken care of.
17. Ramanujan S.
About: Hello! I grew up with my German Shepard mix, Remus, who was my sidekick for 8 years. I now have Anya, a pit mix from Baltimore, who has been my sidekick for 5 years. I have lots of experience walking, giving pets meds, and checking in for food and treats and playtime. I have spent time with and walked loads of different types of dogs. Every dog is unique and I am excited to make friends with yours! I work full time at University of Chicago but keep fairly flexible hours. I can drop in before and after work and check in late at night as well in the Hyde Park area. I can walk your dog and give treats according to your instructions. I can also drop in to give meds or food and let your dog out, depending upon your and your dog’s needs. I am comfortable with small and big dogs.
18. Madison C.
“Madison was absolutely wonderful, I can’t recommend her enough. I have a senior cat with some extra medical needs and she was incredibly patient and kind in taking care of him. I felt at ease knowing my kitty was in good hands with her!”
19. Erin S.
“Erin is an exceptional pet caregiver. She's not only responsible and considerate, but also truly passionate about animals and attentive to their unique needs, regardless of species. She cared for my fish, two cats, and dog with the utmost dedication, following my instructions with a great attitude and asking thoughtful questions when clarification was needed. When I requested updates, Erin enthusiastically sent photos and kept me informed about how everyone was doing. She went above and beyond to make sure each pet felt comfortable and loved: showering my cats with affection, walking my dog daily, and staying on top of my complicated fish-feeding schedule. Erin is now my go-to sitter, and I can’t recommend her highly enough!”
Over 61 pet parents in Kenwood have booked pet sitting
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Pet Sitting FAQs
Frequently asked questions about Rover
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.
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