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 dog.
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Crystal R.

“Crystal was amazing with my reactive border collie! She took her time introducing herself and helped Zuri be super comfortable on a walk when she’s not used to being taking out by others!”


Coretta S.

“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!”


David K.

“Hired David last second to come take my dog out. He was super accommodating. David was so kind and good with my German shepherd puppy. Sent lots of photos and let me know what was going on. Great communication. Would definitely hire him again! Very genuine, nice guy!”




Dalila E.


“We enlist Dalila’s services regularly now that our work schedules have picked up considerably. She’s reliable and been able to come last minute when work threw us a curve ball. She’s been a lifesaver a few times over now and we’re happy to have her as our regular sitter :)”


Taiyo N.

“Taiyo is a very polite, punctual and helpful young man. He looked after our dog very well and I would highly recommend him!”


Kayla S.

“Kayla did a fine job taking care of my two cats. She was prompt and consistent following my directions. Taking photos and posting them was a surprise bonus. I'm fully satisfied with Kayla and will book her again when I need help.”


Janette V.

“Janette was amazing, 10/10 recommend her! She accepted my last minute booking on a very busy weekend, communicating quickly and kindly to coordinate the drop-in. She did an amazing job of communicating before, during, & after the drop-in even when I wasn't able to promptly answer her. Janette even went above & beyond - going out on a limb to greet my very scared cats with treats!”




Emily N.

“Emily did a great job with my cats! She was very attentive to their needs and spent a lot of time with them, and all of her communication was prompt and thorough. Highly recommend!”


Quiana L.
“Quiana has dog sat for me numerous times. She treats my dog as if it’s her own. Always takes him for long walks. Plays endless fetch and even lets my dog sleep in bed with her. Her home is clean and welcoming. She keeps treats on hand even though she doesn’t have a dog. She’s a true dog lover and would be an amazing choice to keep any dog.”


Madeleine G.

“Madeleine has come to look after our fur baby a few times now and has been amazing each time. She’s been punctual, stayed extra if asked, and keeps us updated on the status of our pup. Highly recommend!”


Taylor C.
“Taylor was very attentive to my dog because when he came home to me he was very happy and showed no evidence of mistreatment. She was able to take him on a small walk throughout the day and give him ample potty breaks. She was very nice and responsive with her messaging and I would definitely use her as a sitter again.”




Susan C.

“Susan took excellent care of my two kittens on our week long trip out of state. It was our first time being away from the kittens for more than a day, but I felt reassured after our meet and greet. Susan really does go above and beyond for her clients and their fur babies. 10/10 recommended her :)”


Zareena M.

“Very kind & efficient! Will be booking again! :)”


Amelia H.
“Amelia used to watch my black lab Jasmine when I went out of town or on trips. She used to take really good care of Jasmine, and on top of that she would send me Snapchats of what she and Jasmine were doing, which was really nice.”




Elizabeth D.

“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.”


Lucy G.

“Lucy did a phenomenal job taking care of our kitties while we were gone! She was consistent, professional, and caring. She sent pictures and a little update every day. I knew my cats were in good hands with her!”


Katherine B.

“KT was fantastic with our 13 year old cat, Minnow. They immediately connected and it was clear that they have a real love and care for animals. Was also able to schedule with them in rather short notice, which definitely relieved quite a bit of anxiety on our end. Highly recommended.”




Chi O.
About: I love dogs! I always have, and have my own puppy best friend at home with me. I’m so excited to love on your furry friends just as much as I do mine. I love long walks with lots of pauses for sniffing and exploring, and plenty of indoor playtime with my dog Mini. I’m also big on healthy treats and snacks. Aside from my dog, I’ve also had plenty of fun dog-sitting for other dogs of small to medium size. Choose me to give your pup an exciting, dynamic vacation while you’re gone! I’m currently a student at Booth which means that most of my time is free (class on average only 3 hours a day) and I’m close by to check on pups! I am big on walks, pets, and enrichment interactions to keep pups mind as occupied as their body. That being said, I know you know best and I’ll follow your instructions on treats and playtime to disrupt your dogs routine as little as possible.


Raeanna H.
“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!”


Brian D.


“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!”