Pet Sitting & Drop Ins in Oakland, Chicago

“Crystal was timely and very communicative while watching my cats. I’m so glad to have found her and look forward to scheduling with her in the future.”

“Coretta is amazing! She showed so much attention and care to our pets. I’m so grateful to have found her on Rover. She asked great questions and was very kind and accommodating. Highly recommend!”

“I couldn't be happier with Gabriell's exceptional dog walking services. From the moment I entrusted her with caring for my furry friend, I knew I had found someone truly special. Gabriell isn't just a dog walker; she's a canine companion extraordinaire! Gabriell's passion for dogs is evident in every interaction. She has an innate ability to connect with our four-legged family members, making them feel comfortable and loved from the very start. Her warm and friendly demeanor immediately put my pup at ease, and I could tell that they genuinely enjoyed their time together. I am so glad I found her! Don't hesitate to book you won't be disappointed!”

“Katherine is wonderful! We have a new kitten and an older fella cat, we had to leave town for a week, and weren't sure how the kitten would respond to his first time with us being away, how many things would be broken, and who could be a good fit to keep an eye on things and make sure the boys were well cared for. Katherine is an excellent communicator, provides tons of great information during visits, and gave us peace of mind that our home and kitties were in good hands. If Katherine is available, you'll be lucky to have them!”

“Kayla did a good job checking in on my cats while I was away. She refilled their water, changed their litter, cleaned up vomit, and played with them.”

“David is a great communicator. He followed instructions effectively and asked good questions. We loved the pictures and keeping us in the loop during the visit. He also was so nice and great to interact with over the app. It made our first experience booking someone on here a very pleasant experience. Thank you so much, David!”

“I don't even know how to start this because I cannot recommend Olivia highly enough. Olivia took amazing care of my pup in the worst possible circumstances-- the day I left for vacation, my dog got crazy diarrhea. Olivia made her feel comfortable and safe in my absence, and dealt with the insane poop situation with grace, going the extra mile to get extra supplies from the pet store as needed. She did more than any boarding facility would have done. She's reliable, communicative, cool under pressure, and super nice. You should book her :)”

“Katie is an amazing petsitter! She is a loving caretaker who is detail-oriented and makes sure your dogs’ every need is met. From long walks and yummy meals to belly rubs and ear-scratching, our 2 Weimaraners give her 5 golden paws. She is extremely trustworthy and goes above and beyond!”

“Leslie's exceptional pet sitting skills shine through her attentive and compassionate care for animals. She has taken care of my precious Bonvie several times. Bonvie absolutely loves Leslie. Her reliability and commitment to ensuring the well-being of pets are truly remarkable. She goes above and beyond to create a comfortable and engaging environment, making sure every furry friend feels safe and loved in her care. Her dedication and genuine affection for animals make her an outstanding pet sitter that pet owners can trust with complete confidence.”

About: I have always had pets as a child and the responsibility to care after them like I would my siblings. But as I have gotten older I have been provided the luxury of owning pets I can call my own and raise how I see fit (which is code for spoil). I wont put some long drawn out advertisement of why you should pick me to care for your fur baby, but just understand that everyone tells me how I treat TuTu more like a child than I do the human one 🙂 Thats how much i love pets, and how important it is to make them feel part of the family! And if you decide to trust me with your pet, just know they will always be treated the same while in my care💜 I work a full-time job in IT, but very flexible and mostly remote. So i am pretty open and available when needed. Also very respectful of your time, so i will always be open and communicate any conflicts that may arise. I currently have a 3 year old Shitzhu that is full of energy and love to be around other dogs. Extremely (overly) friendly and very welcoming lol. I also have a cat that is pretty antisocial, so in the instance you would prefer my home, i will put her in her up in her own room. I stay in a duplex, so plenty of room to be comfortable. Also, we go on multiple walks a day so plenty of exercise will be provided along with belly rubs.

“Brian did a drop-in visit to meet our dog Zoey, who has a really hard time with strangers! Zoey was adopted so we don't know her full history, except that she distrusts new people and dogs. Therefore, it's important for us to set up meet and greets that help everyone acclimate to each other, and Brian was a fantastic fit. Brian is detail oriented and inquisitive — he really takes the time to ask questions and learn as much as possible about your fur baby and what has worked - and he is extremely communicative. It was clear that Brian has experience with reactive dogs - and his belief that Zoey was just like any other dog underneath all the reactivity - made us confident that he could succeed in gaining her trust over time. Brian did a great job with Zoey during his meet and greet and we are grateful for his patience and skills!”

“My dog loves Viola! She’s one of the very few people that he truly feels the most comfortable around, so she’s one I know I can depend on to dogsit for me whenever I travel and can’t take him with me, and I’ve never had ANY problems when I come to pick him up after. Viola is attentive, caring, and very responsible when it comes to administering his medications and feeding him according to his special diet. Of course I’d recommend her!”

“This is the third or fourth time we’ve used Susan to watch our kitties. They all have different temperaments and moods and she’s great with all of them. Will definitely continue to use her for future sittings.”

About: Hi, nice to meet you and thank you for coming to visit my page 😊. I’m Kelsey!!! I work full time for Rover because I love animals of all shapes and sizes and have since I was a small child so this is my dream job. I had a pet Black Lab Midnight however he passed away when I was younger after 14 years of a good life with me and my family. I currently have two cats one is Oliver and the other Yemaya and I love them both very much and everyone who meets them tells me I’m lucky to have such amazing fur children since they’re so well behaved minus the zoomies they sometimes get 😂. I’ve been caring for animals for 15+ years including dogs, cats, and small animals. I love seeing a dogs happy smile when we’re taking a walk and hearing a cats pleased purr when they get scratched behind their ears. 😊 I am open to any suggestions 👂 from the parent of the pet or pets, on making your fur baby comfortable with me since I’ll treat them like family while I am dog walking or maybe even pet sitting in your home. Thank you for letting me be your Pet Caretaker I promise to treat them like family. ❤️ Also, I’m knowledgeable on how to administer medications, vitamins, and grooming pets. I’m able to control leashed animals over 50 lbs. Rover is currently my full-time job, I am available on weekdays for dog walks and pet sitting on the weekends when you have to run errands and don’t wanna leave your fur baby home alone. I live in a very secure building so my pet has never escaped or even left the apartment. The yard is fully fenced in with a wood fence and I also keep my new dog on the leash at all times unless we’re in the yard playing.

“I've worked with Shiri in many settings and shi has always been a compassionate and reliable coworker. That doesn't change when it comes to working with animals, as I have seen first hand. Shi is sweet, caring, & gentle when approaching and is great at noticing little things about pets behavior and possible needs. Shi is great at training and being creative with new activities. Shiri gives great pet care and my fluffy baby lynx loves to snuggle up next to them. I definitely know whoever works with Shiri will be pleased and so will their fuzzy friend.”

“Ashley is a super mom to her kids and her cats! She also took care of my personal cat and my rescue cats while I was on vacation. She is a caring and kind person who i fully trust with my special needs kitties many of which have special diets! My cats and I all love Ashley! 🥰”

“Raeanna is reliable, responsible, and an all-around awesome person! She truly loves animals, and I can always count on her to keep my pets safe and happy while I am away. She also goes above and beyond to keep my home in pristine condition. I will continue to use Raeanna for pet care when the need arises!”

About: I am a college grad and former dog owner with previous experience working as a dog sitter since high school. I love pets immensely, and am so excited to meet yours! Every dog I get to greet is a gift, and I treat them as such. Through my own experience as a dog owner, alongside my diverse experience with other dogs, I have learned a lot that I get to bring to these new situations. I know how vital calmness can be, and keep myself patient. I know every dog is different, so please share everything you can about your animal and all their quirks! Getting to interact with animals is so much fun and so fulfilling, I wish to spend more of my time doing it when I can. I currently work from home, so my schedule is incredibly flexible! I'm available for walks throughout the week and can stay with your fur baby as need be. I like to keep the care of your pet as close as possible to their normal routine, so please keep that information clearly written out if possible, or we can write it out together!

“Elizabeth watched our cat Chachi and she did an amazing job! He’s typically very shy but Elizabeth was so gentle and patient that he immediately warmed up to her. Having Elizabeth watch him gave us a really big sense of relief and made us feel safe leaving him knowing he was in such good hands. I can tell she really cared for him and enjoyed his company. I hope to always use Elizabeth when we’re out of town.”

“Olivia is a very attentive and responsible cat owner. She has taken wonderful care of her cat Robin. She has experience growing up with two Corgis, who she was in charge of walking every day, and never fails to stop to pet a dog on the street! She has also spent years volunteering at an animal shelter acclimating dogs and cats in Houston, TX. I cannot imagine anyone more suited to be a dog walker or sitter!”