Pet Sitting & Drop Ins in Jefferson Park, Chicago

“We are very pleased with our first drop in with Jackie. Our dog is very anxious around all people and Jackie understood Nabi’s special needs, was on time and very communicative! We will be requesting more drop-ins with Jackie!”

Alice K.

“Coleen is a wonderful dogwalker! I always get a thorough update and photos after each walk, and our pup Frankie is always well taken care of during Coleen’s visits. Thanks so much, Coleen!”

Melissa M.

“As a new dog dad and learning as I go finding a sitter has been so nerve racking. Getting in contact with Robert was a life saver. Was very communicative, respectful of my space. My tiny puppy seems to love him. Made me feel comfortable through the visits and shared some cute pics of my fur baby. Would highly recommend and will be booking with him again soon.”

Dean B.

“Jessica has looked in our 3 cats a couple times now and she’s amazing at not only feeding and playing with our cats, but administering oral medication, shots and asthma inhalers. She will put your mind at ease about your pets.”

Kate K.

“Karina did a great job watching our 14 year old pet cat Frankie. We were gone for two weeks and had never been separated from him for that length of time. With much trepidation about leaving him, Karina reassured with with daily updates and photos. This was great help and allowed us to enjoy our trip with no worry or concern about Frankie. We will definitely use her service in the future and I highly recommend her for any pet sitting job. John I”

John I.

About: I love cats, playing with them, and of course taking their cute pictures. My pet sitting experience started from my friends’ cats and transitioned into taking Rover clients. I’d say for me the toughest part is saying good bye🤗 I can do cat boarding and also drop in visits for cats and dogs. Looking forward to meeting more pets 🤗 My routine is working from home Monday and Friday, the rest of the work days I go to office. On the days I go to office I can walk and play with your pet after 6 pm. Usually when cats stay with me I give them a lot of space, they can jump and play everywhere in my 2 bd apartment , but if you have specific restrictions I could adjust the environment. If your cats like to be pet and you provide me with instruction, I would love to pet them when needed. If they like to sit back and just watch from distance thats great too! Same thing for dogs, I am very respectful of their space and needs.Only love and respect 😍

“Arlene has watched our dogs several times over the past year. She takes such great care of them, and it’s amazing to not have to worry about the dogs while we are gone!”

Sarah G.

“Janine was very friendly and she came to meet Wendy the week prior to the visits she would be having with our pup. Wendy was happy to meet her as soon as we let her off the leash. She sent pictures every visit and my Wendy looked very happy. She was responsive if I sent a message and sent me updates as well without being asked. I will definitely book her again in the future if we need another dog sitter!”

Danielle C.

About: I’ve been a dog owner for most of my life, with experience caring for dogs at every stage, from playful puppies to sweet senior dogs. I’ve personally trained all of my own dogs and have a strong understanding of different temperaments and needs. My current dog can be reactive toward other dogs, so I’m very mindful about handling dogs with similar sensitivities and ensuring their environment is safe and comfortable. In addition to caring for my own pets, I’ve also been a sitter for both large and small dogs, and I always take the time to make sure they feel secure, loved, and well cared for. I’m currently a master’s student taking online classes, which gives me a flexible schedule and plenty of time to dedicate to pet care. Working with Rover is how I support myself and pay for school, so I take every booking seriously and am committed to providing reliable, loving care for your pets. While I’m unable to host pets in my home due to my own dog’s reactivity, I truly look forward to meeting your furry friend in their own space or taking them out for a nice walk. Your pet’s safety is my top priority. I’m always alert to potential dangers and will treat your pet with the same love and care I give my own. You can trust that they’ll be in safe, capable, and compassionate hands.

“Jo is absolutely amazing, 10/10 would recommend!! She took perfect care of my two cats and went above and beyond to make sure all of their needs were met. It was a huge weight off my shoulders knowing that they were in super capable hands while I was away. Definitely planning on re-booking with Jo for future travel!”

Ketia J.

About: I’ve loved dogs since I adopted my first puppy at age 9– a Labrador, chow chow mix. With him I shared my first experiences walking, feeding, and playing with dogs. At age 12, I adopted a German Shepard, golden retriever mix that was his best companion. Living with two dogs taught me the importance of friendship and care between humans and animals. Over the years I’ve walked, house sat, fed, bathed, and administered medication while pet sitting and feel confident with these tasks. Although, my favorite thing is to cuddle up and show pets affection. I’d love to extend my love for animals to your darling pet and integrate any care requests you have. I’m currently working part time with a very flexible schedule, so I can be available for drop in walks, check ins, etc, throughout the day. I always approach new pet friendships with care- slowly and by gauging the comfort of the animal. I let the animal approach me first if a little hesitant so that they can get to know me. I offer affection to build trust and can also offer treats to further that. I’m attentive and responsive to the needs of the pet if any. For example, if a dog is communicating a need to go outside or is boundary setting I am responsive to that.

“Keri was wonderful! Super communicative and even caught an urgent medical issue that my cat developed while we were out of town (urinary blockage). If it weren’t for her paying such close attention and noticing a change in my cat, he probably wouldn’t have made it. I am forever grateful for her!”

Amanda L.

“This was the first time I have ever left my babies and Kayla not only did a great job but she made me feel comfortable about it! Pictures, played and did everything I needed to feel okay leaving my babies behind for a few days.”

Rebecca B.

“This was my first experience with Rover and Adrian made it a dream! He watched my 11yr old sassy black cat Kiki. He communicated with me every drop off, kept me updated with the cutest photos and followed all instructions perfectly. Even when our kiki was being grumpy, as expected, he still went above and beyond to try and get some enrichment in every visit. I will never forget the hilarious photos of our cat angry, side eyeing or being disinterested in his favorite toy. Protesting the absence of his owners. 😂 I would definitely rebook with Adrian in a heart beat!”

Destiny C.

About: I believe pets are the best thing that has happened to human kind and should be appreciated for all the joy and love they bring us. I grew up with and helped care for a cat colony for 15+ years. My favorite dog growing up, Bobbie a cute Pekingese, had seizures and my favorite cat, coffee an American short hair, had diabetes. I can't remember a time in my life where my family and I weren't watching or taking in someone's dog or cat wether it was only a day or for years. Now that I have my own space I would like to continue the tradition of sharing my home with fur friends. With all the animals I've taken care of I'd like to think I'm qualified for this job. I'm excited to meet and take care your best friend and give them all the love I possibly can. I'm always ready to take care of anyone's pet whenever need be. I'll save your last minute vacation. Call anytime day or night. No joke, always free :3 I have a nice spacious yard to take dogs out and play catch in. My household is a child free zone and is kept clean. There are no small things for them to eat or choke on and most everything is stored off the floors so there is nothing that can get into. Pets are allowed on beds and couches unless you prefer them not to. The house is kept cool in the summer and warm in the winter.

About: 🐾 🐶 I have a Beagle mix, and a German Shepard mix at home. I also grew up with Irish Wolfhounds—big hearts, big fun! 🐕‍🦺 My family has always kept pups in our house. From playful mixes to fancy poodles, I've seen them all! I do also have (2) 🦜 birds, (2) 🐟 fish and (3) 😸 kitties I have raised since they were born. I am more than happy to help out while you’re away! ♥️🐾 I am available at all times Sunday after 7:00 PM CST through Friday before 3:00 PM CST as well as at any time on holidays! I do have a fenced in yard. I take my dogs out for walks. When we do go in the yard, I never let my own dog out without going out with them myself as well to monitor.

“Tina took great care of my dog while we were gone for four days. She was extremely responsive, attentive, and flexible. Will definitely be using again!”

Ryan M.

About: I’ve spent the last 15 years fully immersed in the pet world—working in dog daycares, doing walks, baths, kennel cleaning, playtime supervision (and yes, even the occasional breakup of dog fights when things get too wild). I’ve also worked closely with vets in an animal hospital setting, always asking questions and learning everything I can about animal care and health. I’ve been a lifelong pet parent to both cats and dogs, and I’ve picked up basic puppy training and a strong understanding of dog body language along the way—so I know how to help our furry friends feel safe, happy, and understood. I work from home, which means I can give your pet plenty of attention throughout the day. One thing to note: my 6-year-old sidekick is always with me. He’s been doing this since birth and is basically a tiny animal whisperer—super respectful of animals and never pushes boundaries. My rates reflect not only my hands-on experience but also my background in animal behavior and health. I treat every pet like my own, and I’m here to make sure your fur baby is well-loved, safe, and having a blast while you’re away. Just like you, I’ve got a work schedule; but the way I like to put it is: I’m simply stepping into your shoes while you’re away. Since I work from home, I’m able to keep a close eye on your pet and make sure they get plenty of potty breaks, attention, and cuddle time throughout the day. It’s all about keeping their routine feeling as normal and cozy as possible. I like to go over details with pet parents beforehand, get to know the pets favorite things to do, or places to go. That way it’s not such an abrupt change for them when owners are away.

“I have two cats. One is a complete sweetie except he is now almost 17 and is on multiple medications. In discussion with the vet before my trip, the vet had "ideal" and "essential" medicine dispersal. In our meeting to go over things, it was clear she understood his medical issues, the various medicines and their priority and importance. Kimberly was diligent in administering the medicine most essential and getting at least one daily dose of the others, despite the cat hiding from her on several visits. (He is easy for me but I am told by prior sitters he fights the pills). What pleased me was that she kept him in good health without stressing him out to the point where he acted out like he did with previous sitter determined to administer pills. She knew how to balance stress and medicine. If you have a cat with health issues, I highly recommend Kimberly. Since my other cat is a high strung rescue who hides from everything, Kimberly did not interact with her directly but she reassured me of signs of eating, litter activity to show she hadn't escaped when she hadn't showed after 5 days. (that is very typical of this cat, even for longer visits so no reflection on Kimberly).”

Constance M.

About: Living directly across from Jefferson Park is the perfect location for any dog. It’s a safe and friendly neighborhood with Wilson and Portage Parks only a mile down Long Ave. That’s 3 BIG parks all within a single mile. Portage does have a fenced dog park, but unless explicit permission is given, I never bring a clients dog into a dog park out of safety precautions. Your dog might be friendly, but I can’t guarantee other dogs will be, therefore I air on the side of caution. When your dog is with me they will have full access to the condo. If you prefer them not to be on furniture, I won’t allow it, but they are more than welcome to snuggle on the couch or bed! I can accommodate up to 3 dogs at a time. I ask that either your dog be dog friendly or if your dog is not dog friendly, check my calendar to ensure no one else has booked. Return clients with non-dog friendly pups will be considered and I will block the second booking slot with compensation consideration. I accept dogs of all sizes and breeds. If you prefer an experienced sitter who knows how to manage and care for a reactive pup I am willing to do drop in visits while you are away, if I cannot accommodate in my home due to active booking(s). From personal experience I FULLY understand what it is like to have a non-friendly dog, but trust a certain person to watch them. I will always do my best to accommodate the needs of a client who trusts my experience with their fur baby! I have years of experience with larger dogs presenting behavioral issues or aggressive tendencies. My rescue, Elwood who passed away in 2019 was on the protective/aggressive side (to say the least) and even after training and socialization, his habits couldn’t be broken. I know the body language signs and how to calmly react. I also know what it is like to love your dog so much and at the same time feel helpless because they can’t be trusted ‘just anyone’ without worry. I also share custody of a Bull Terrier (reactive also) named Vincent with an ex. Yes, like a child! We switch based on work travel schedules and if Vincent is with me my calendar is blocked. I also travel abroad frequently for work so I am only able to have my schedule open a couple months in advance. IF YOU ARE A REPEAT CLIENT OR TRUST MY EXPERIENCE, PLEASE MSG AND I MAY BE ABLE TO ACCOMMODATE. I never want to cancel a booking therefore it’s best to keep open what I know I can do. I take Rover and dog sitting very seriously, I also want to respect and be transparent with every client’s time and expectations. I have a large crate with bedding, dog stairs for smaller dogs or hip issues, a medium and large harness with a secure seatbelt (if car rides are allowed or transport is needed), toys, feeders, treats, brushes and anything a regular dog owner would have. Please bring your dog’s favorite toys, blankets, coats/sweaters, bed, bowls, treats IF DESIRED. The only things 100% necessary would be their specific food, treats, medication and coat/boots (weather depending). Please let me know if there are any training exercises, routines, walk, feeding, wake and bed time or medications your dog may need. I have a vehicle and can provide transport with harnesses and seatbelts, if you are unable to drop off/pick up. (see fee) I gladly send updates and pictures while you are away - my goal is for you to feel secure knowing your baby is in good hands and enjoying their own vacation.🐶 If you have questions about my home, neighborhood, or experience, please do not hesitate to reach out! Thanks, Casey Work from home - if I’m teaching a virtual class, which are based overseas my schedule is blocked. I teach overnights and sleep during the day. I also travel abroad weeks at a time if I’m teaching in person, so my capacity to have a dog of my own 100% of the time again is not feasible and Rover is a great option for me to care for a dog and have some companionship when my ex has our dog. I have a large crate if your pup is used to being crate trained and feels secure inside their little hut. I know my dog liked to sleep in his crate when he was done for the day and wanted a darker more secure place than the couch. I care for your pet just as I would my own with affection, exercise, giving them space/time to rest and adhering to all safety precautions around other animals or people we may meet outside.