Pet Sitting & Drop Ins in Woodlawn, 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 Woodlawn pet sitters
“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.”
“Coretta as ever did a wonderful job with our cat. She sent photographs showing that our cat was happy and following his usual routine, despite the fact that we were away. She always sends detailed information and lots of pictures which really makes us feel so much better. And in this holiday season, where there tend to be a lot of packages that pile up, she was careful to collect them all and even send photos of all the packages that arrived - which was so nice of her to do. She follows our instructions and really cares that she is doing a good job. If you want a very conscientious cat sitter who will take great care of your cat and really care about them, I definitely recommend her!”
“I could not be more grateful of Abi taking care of our dogs. I am assured that our fur babies are well taken cared of- especially with Eiko being a senior dog with special needs. She is attentive to their needs and communicates well of any issues that may arise every time.”
“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 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!”
“Megan is so attentive and her updates are so cute!! I can tell my kitty was well taken care of and stimulated. This is my first time booking a cat sitter and she was a great one. Would recommend booking with her!”
“Laurel has been great with our dog! Rufio was super happy and she was very prompt with visits, great to work with on scheduling, and very friendly! Plus got some super cute pics of the pup during her visits :)”
“Samantha did an amazing job taking care of my kitties while I was out of town! She sent great pictures and let me know how they were doing each day. Knowing that she was taking great care of them made traveling so much less stressful.”
About: I've had dogs in my life since day one, and have ample experience caring for furry friends, including my neighbors' pups. There's nothing quite like sharing a walk or run with a dog and burning off some energy together – it's where the real bond happens! My part-time work schedule, primarily in the mornings, provides ample flexibility to dedicate quality time to your pet. I'm committed to ensuring your furry friend receives multiple walks daily and feels completely at ease and happy during their stay. I'm also available for consistent communication to keep you updated on their well-being throughout the day. My home offers a secure, fully fenced backyard and a peaceful neighborhood perfect for leisurely dog walks. Plus, I'm just steps away from a dog park for extra energetic playtime! When caring for your pet in your home, I prioritize maintaining their familiar routine and ensuring a safe, comfortable environment by following your specific instructions meticulously. Your pet's well-being and your peace of mind are my top concerns.
“Malcomn took such great care of my cat, Kashi. He was very communicative and sent updates and photos everyday which I thoroughly appreciated. Kashi and I are so grateful for Malcomn’s service!”
“Rebecca was so patient and sweet with our boy. She showed up every visit as promised, left great notes and pictures. This was our first time using a pet sitter and leaving our boy; she made it so much easier on us and reassured us he was doing well. We will without a doubt use her again for our future trips 🤍”
“Leah was great! She was showed up for feedings exactly when we requested, and her updates and photos let us know that our fur babies were cared for with attention and love! We were able to relax and enjoy our time away knowing they were in great hands.”
About: I'd love to meet your dog or cat and you can trust I'll treat them like my own. I know how to keep them safe and happy while you're away. I'll send you a good photo too my camera roll is mostly all photos of dogs. I work freelance so my availability is flexible. I prefer we conduct a meet and greet first, to make sure your pet is comfortable with our plans! Walks and care provided in clients home only, I can't provide boarding. I will be sure we establish comfort in our meet and greet, please be sure to provide vet information in case of any unexpected emergency.
About: I’ve always had a deep love for animals, having grown up with both cats and dogs as part of my family. Many of them needed extra care as they aged or faced medical challenges, which taught me how to provide compassionate, hands-on support. I have experience administering medications, assisting injured pets with mobility, and ensuring they feel safe and comfortable in every situation. My natural patience and attention to detail allow me to connect with animals and provide the thoughtful care they deserve, whether they’re playful puppies or senior companions needing a little extra TLC. I’m currently a student at the University of Chicago, which gives me a flexible schedule to dedicate quality time to your beloved pets. I understand how important it is for them to feel happy, comfortable, and cared for while you’re away, and I’m committed to providing them with plenty of attention, affection, and companionship. Whether in my home or yours, I ensure your furry friend is well-fed, hydrated, and receives plenty of attention and care. I take the time to keep them engaged and stimulated with activities they enjoy, whether it’s playtime, walks, or simply some cuddles and companionship. I understand it can be tough for pets to be apart from their owners, so I focus on making them feel as happy, comfortable, and loved as possible during our time together.
About: I bring hands-on experience and genuine love for animals into every pet-sitting job. I have two dogs of my own (ages 7 and 4) whom I trained myself from puppyhood—including potty training by 6 months! I groom them myself regularly, take them on daily walks, and have experience administering medications for allergies, ear infections, preventative care, and post-procedure care. Whether your pet needs structured training support, gentle senior care, or just someone who truly understands their needs and routines, I'm here to offer reliable, compassionate service. Your pets will be treated like family—because that’s exactly how I treat my own. As a medical student who primarily studies from home, I have a very flexible and consistent schedule. Outside of 2-3 hours a day when I’m on campus, I’m home and fully available to care for pets. This allows me to give them plenty of attention, regular walks, playtime, and any needed care throughout the day. Having a structured but home-based routine makes it easy for me to prioritize your pet’s needs and keep them happy, healthy, and comfortable while you're away. Whether I’m caring for pets in my home or in a client’s, my approach is all about providing a safe, loving, and low-stress environment that mirrors their usual routine as closely as possible. In my home, pets have a calm, pet-friendly space where they can relax, play, and enjoy plenty of attention. I do daily walks, structured feeding times, and lots of one-on-one interaction. If I’m caring for pets in their own home, I make it a priority to maintain their normal schedule—walks, meals, playtime, and any special instructions—so they feel secure and comfortable in their familiar surroundings. I’m also experienced with medication administration and basic grooming, and I keep pet parents updated regularly with messages and photos so they can feel at ease while they’re away.
“Rebecca was fantastic with our cat, Theo! We're new to the area so it was such a big comfort to know he was being well taken care of while we were out of town. Rebecca was intentional about following his quirky routines, sent us lots of pictures and videos, and made sure to check in even about the little things. We will definitely be reaching out to her again! :)”
Loving pet sitters in your neighborhood
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Cassandra H.
“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.”
Coretta S.Star Sitter
“Coretta as ever did a wonderful job with our cat. She sent photographs showing that our cat was happy and following his usual routine, despite the fact that we were away. She always sends detailed information and lots of pictures which really makes us feel so much better. And in this holiday season, where there tend to be a lot of packages that pile up, she was careful to collect them all and even send photos of all the packages that arrived - which was so nice of her to do. She follows our instructions and really cares that she is doing a good job. If you want a very conscientious cat sitter who will take great care of your cat and really care about them, I definitely recommend her!”
Abi S.Star Sitter
“I could not be more grateful of Abi taking care of our dogs. I am assured that our fur babies are well taken cared of- especially with Eiko being a senior dog with special needs. She is attentive to their needs and communicates well of any issues that may arise every time.”
Tamara J.Star Sitter
“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 T.Star Sitter
“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!”
Megan D.
“Megan is so attentive and her updates are so cute!! I can tell my kitty was well taken care of and stimulated. This is my first time booking a cat sitter and she was a great one. Would recommend booking with her!”
Luwam Z.Star Sitter
“Thank you!!!”
Laurel M.Star Sitter
“Laurel has been great with our dog! Rufio was super happy and she was very prompt with visits, great to work with on scheduling, and very friendly! Plus got some super cute pics of the pup during her visits :)”
Samantha E.Star Sitter
“Samantha did an amazing job taking care of my kitties while I was out of town! She sent great pictures and let me know how they were doing each day. Knowing that she was taking great care of them made traveling so much less stressful.”
Mia L.
“As a former rover walker, and someone who’d never used anyone to sit for my senior dog with many needs, I was nervous about hiring someone for daily walks. Mia made me feel at ease, and before my trip, we did a trial walk while I stayed at home. My dog Pepper came back smiling and wagging, which he hasn’t done on our walks in a long time. She said he was running around with the other dogs, which was clear from his exhaustion, another thing he doesn’t normally do. Over my trip she took many videos of them out on walks, and has become my go-to for anything pepper related. I’m going on a longer trip and feel comfortable with her staying over and watching him for the duration. She’ll be administering medication and feeding him dry food as well as small amounts of boiled chicken and rice, which she’s done when I’ve left in the past too. The last few trips I arrived home to a happy and healthy dog, and he hadn’t gained or lost any weight, which I was concerned about. Overall, I highly suggest Mia as a dog walker and caretaker, as she’s trustworthy, clearly good at it, and enjoys spending time with pepper as an added bonus. 10/10!”
Malcomn F.Star Sitter
“Malcomn took such great care of my cat, Kashi. He was very communicative and sent updates and photos everyday which I thoroughly appreciated. Kashi and I are so grateful for Malcomn’s service!”
Ava M.
“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.”
Rebecca I.Star Sitter
“Rebecca was so patient and sweet with our boy. She showed up every visit as promised, left great notes and pictures. This was our first time using a pet sitter and leaving our boy; she made it so much easier on us and reassured us he was doing well. We will without a doubt use her again for our future trips 🤍”
Leah C.
“Leah was great! She was showed up for feedings exactly when we requested, and her updates and photos let us know that our fur babies were cared for with attention and love! We were able to relax and enjoy our time away knowing they were in great hands.”
Bola A.Star Sitter
“Bola’s wonderful! We’re glad to have her support with our dogs.”
Jennifer D.
“I’ve known Jennifer for nearly thirty years. She has always had pets since I’ve known her, and she has always been a loving caregiver to them. I would absolutely recommend her as a responsible caretaker for your pets.”
Jared B.
About: I’ve always had a deep love for animals, having grown up with both cats and dogs as part of my family. Many of them needed extra care as they aged or faced medical challenges, which taught me how to provide compassionate, hands-on support. I have experience administering medications, assisting injured pets with mobility, and ensuring they feel safe and comfortable in every situation. My natural patience and attention to detail allow me to connect with animals and provide the thoughtful care they deserve, whether they’re playful puppies or senior companions needing a little extra TLC. I’m currently a student at the University of Chicago, which gives me a flexible schedule to dedicate quality time to your beloved pets. I understand how important it is for them to feel happy, comfortable, and cared for while you’re away, and I’m committed to providing them with plenty of attention, affection, and companionship. Whether in my home or yours, I ensure your furry friend is well-fed, hydrated, and receives plenty of attention and care. I take the time to keep them engaged and stimulated with activities they enjoy, whether it’s playtime, walks, or simply some cuddles and companionship. I understand it can be tough for pets to be apart from their owners, so I focus on making them feel as happy, comfortable, and loved as possible during our time together.
Dominique F.
“Dominique is really great always dependable I am a returning customer and as long as she’s doing this she is the only person I will trust with my dog son.”
Keianna M.
About: I bring hands-on experience and genuine love for animals into every pet-sitting job. I have two dogs of my own (ages 7 and 4) whom I trained myself from puppyhood—including potty training by 6 months! I groom them myself regularly, take them on daily walks, and have experience administering medications for allergies, ear infections, preventative care, and post-procedure care. Whether your pet needs structured training support, gentle senior care, or just someone who truly understands their needs and routines, I'm here to offer reliable, compassionate service. Your pets will be treated like family—because that’s exactly how I treat my own. As a medical student who primarily studies from home, I have a very flexible and consistent schedule. Outside of 2-3 hours a day when I’m on campus, I’m home and fully available to care for pets. This allows me to give them plenty of attention, regular walks, playtime, and any needed care throughout the day. Having a structured but home-based routine makes it easy for me to prioritize your pet’s needs and keep them happy, healthy, and comfortable while you're away. Whether I’m caring for pets in my home or in a client’s, my approach is all about providing a safe, loving, and low-stress environment that mirrors their usual routine as closely as possible. In my home, pets have a calm, pet-friendly space where they can relax, play, and enjoy plenty of attention. I do daily walks, structured feeding times, and lots of one-on-one interaction. If I’m caring for pets in their own home, I make it a priority to maintain their normal schedule—walks, meals, playtime, and any special instructions—so they feel secure and comfortable in their familiar surroundings. I’m also experienced with medication administration and basic grooming, and I keep pet parents updated regularly with messages and photos so they can feel at ease while they’re away.
Rebecca B.
“Rebecca was fantastic with our cat, Theo! We're new to the area so it was such a big comfort to know he was being well taken care of while we were out of town. Rebecca was intentional about following his quirky routines, sent us lots of pictures and videos, and made sure to check in even about the little things. We will definitely be reaching out to her again! :)”
Over 23 pet parents in Woodlawn have booked pet sitting
Woodlawn pet parents share their Rover experiences
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.
Timothy was great with our sometimes skittish cat. We received daily updates and pictures immediately after all visits. You could tell that our cat liked him and that Timothy understood his nature. Timothy was more than pleasant, great communication, super prompt, and made us feel that our cat was safe and cared for. We would definitely hire him again.
I cannot say enough positive things about Emma! She is communicative, thorough, follows instructions perfectly, and genuinely cares about my pets. This is my second time booking with her, and I felt 100% comfortable and confident that my kitties were well taken care of. Whether it’s a short trip or a long one, I’ll only book Emma!
I can't say enough wonderful things about Peyton as Sheba's pet sitter! Sheba absolutely adored having Peyton around, and it was clear that she enjoyed the company and time spent outside. Peyton went above and beyond to make sure Sheba was well taken care of, offering plenty of love, attention, and outdoor playtime. If you're looking for someone who is reliable, caring, and truly understands pit terriers, I highly recommend Peyton for anyone's pet sitting needs. She’s fantastic!
Leaving your pets and trusting a stranger in your house for a month is hard. Ms Katerina made it a pleasure. She was wonderful, taking the time to meet the dogs before the trip and co-ordinating with me on the logistics. She made me feel very comfortable before I left and was very diligent in her visits and care. The dogs seemed to love her and looked happy in the house in the pictures she sent everyday. I recommend her very highly. Thank you very much Katerina for taking care of my babies
Popular requests near you
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It doesn’t happen often, but if your pet sitter has to cancel, we’ll work with you to find a new sitter.
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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 Woodlawn.
Rover makes it easy to find Woodlawn 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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