Pet Sitting & Drop Ins in Armour Square, Chicago, IL

“This was my very first time booking with Rover and Cassandra did a great job. It definitely put my mind at ease having her take care of our dog while we were away. Thank you!!”

Alyssa Y.

“Molly was amazing with our sweet puppy Ozzy! We feel so lucky that she even spent extra time with him! This was our first time leaving him without someone and we are beyond happy with how well Molly took care of him!”

Whitney W.

“I have booked with Eunice multiple times now (some very last minute bookings) and she always does a great job checking in and taking care of my Doberman. Eunice always makes sure my energetic dog gets enough attention and exercise throughout the visit.”

Asia A.

“Michelle took such wonderful care of my cats! She’s incredibly nice and attentive. She provides excellent visit reports with the cutest pictures to let me see how they were doing which made me feel better about being away.”

Emily K.

“Molly did drop-in visits for my cat Maizie while I was out of town and she was great! Maizie can be shy and anxious with new people and Molly was very patient with her. Molly was also willing to administer Maizie's daily oral medication (and to build the necessary trust with Maizie to do so), which was very important to me. I also appreciated how communicative Molly was and how quickly she responded to questions I had while I was away. I would definitely recommend Molly for cat-sitting/cat care!”

Esther I.

“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.”

Elizabeth & Monica H.

“Thank you for a great job!”

Jim C.

“Paige was awesome and sent me the cutest photos of tai. I had to book last minute and she was awesome”

Alyssa S.

“Sarah is professional, caring, and communicative and gave regular updates which I really appreciated. My cat was totally relaxed when I got home. Sarah is my new go to cat sitter!”

Zoe A.

“Jason is great! He’s very responsive and my poodle pup loves him. I highly recommend him and will be using him whenever I need someone to drop by and help out when I’m busy.”

Nick S.

“Erin did a great job with our cats. She hit all of the scheduled visits and sent pictures each time. The boys filed no complaints upon our return. I would rebook in the future.”

Charles K.

“David very clearly LOVES animals. He spent the time to make sure our cats were well loved and cared for and even went out of his way (literally) to make it out to our place over the holiday weekend. I would recommend David for any services you may need!”

Sarah W.

“Mariam did a fantastic job watching our cat! She was very communicative and professional; she updated us after every visit and sent lots of pictures. 10/10 would recommend and will be using her services again!!”

Mae J.

“Julianne took great care of my two cats for the weekend - she was super easy to communicate with and followed all of my directions exactly. Would highly recommend her!”

Audrey E.

“Andi is the best! She took such great care of my cat and I felt comfortable that he was in good hands. I came home to a happy and healthy boy. She was also super flexible and helpful with my schedule.”

Madeline N.

“Daphne was amazing with our fur babies and gave them all the love while we were gone. She was as punctual, professional and caring. She was as excellent with communication and follow up. We will use her service again knowing the dogs are taken care of.”

Petia O.

About: • Lifelong pet owner with hands-on experience caring for dogs of all ages, breeds, and temperaments • Comfortable with feeding schedules, medication administration, and special dietary needs • Experience with crate training, basic commands, and leash manners • Knowledge of dog body language and signs of stress or illness • Confident with high-energy breeds and senior dogs alike • Able to handle multiple pets at once • Regularly walk dogs in safe, dog-friendly neighborhoods and parks • Provide both high-energy walks and relaxed strolls tailored to your dog’s needs • Keep dogs mentally stimulated through sniff walks and playtime • Familiar with using different harnesses, leashes, and walking tools • Keep your pets comfortable in their own home with regular check-ins and companionship • Maintain routines for feeding, potty breaks, and bedtime • Provide updates, photos, and videos so you always know your pet is in good hands • Water plants, bring in mail, and keep your home tidy while you’re away • Comfortable with litter box cleaning, feeding, and playtime • Experience with shy or anxious cats—patient and gentle • Can care for small pets like rabbits, hamsters, or birds I’m available any day and time that works best for you—except Sunday mornings. On Sundays, I’m free after 3:00 PM. Whether you need early morning walks, mid-day drop-ins, or evening snuggles, I’ve got you covered! When caring for pets in my client’s home, I do my best to keep their routine consistent so they feel safe and comfortable. I follow all feeding, walking, and medication instructions carefully, and make sure they get plenty of attention, playtime, and affection. I respect the home, clean up after the pets, and always keep you updated with messages and photos so you have peace of mind. If I’m caring for pets in my own home, I make sure they have a clean, cozy space to relax and feel at home. I provide regular walks, playtime, and cuddle sessions. I also pay close attention to how they’re adjusting to a new environment and take extra care to make them feel calm, loved, and secure. Whether your pet is high-energy or low-key, I adjust to their needs and treat them like family.

About: I’ve been around animals my whole life and have years of hands-on experience in both pet rescue and the pet wellness world. I worked at an animal shelter in Texas, caring for rescued dogs and cats—feeding, cleaning kennels, giving vaccinations, and helping animals feel safe and loved. I also spent over two years as an assistant manager at Kriser’s Natural Pet in Chicago, where I learned a ton about nutrition, behavior, and holistic care. These days, I’m a work-from-home dog mom to my own 7-year-old rescue pup (who thinks he’s a cat—yes, he has a window perch)! 🐕🐈‍⬛ I’m comfortable with dogs of all sizes and energy levels, and I have experience caring for senior dogs and administering medication. I don’t offer puppy care, but I’m always happy to tailor my approach to your dog’s personality - whether that means a long walk, a play session, or just being their calm companion while you’re away! 🐾 I work from home Monday to Friday, so I’m pretty flexible with breaks to give your pup some love and walks. I’m usually free early mornings before 8 a.m., midday from 12 to 5 p.m., and evenings after 7 p.m. during summer — hoping to walk dogs pretty much every day, as long as you’re nearby! Last-minute requests happen sometimes, but not too often, and I’m not available on Thursdays. I’m juggling school too, and will be off for two weeks in October for my honeymoon (woohoo!). At home, my rescue dog Shiney and I spend lots of time playing, walking, and chilling during my meetings, so I know how important quality pet time is. I’m all about short visits and long walks, and I’m happy to work around your schedule to make sure your dog gets exactly what they need. I don’t do boarding or daycare, but I’m happy to stay overnight at your place so your pup can chill in their own comfy home. Whether it’s a quick walk or a sleepover, I’m all about keeping your dog safe, happy, and feeling loved! I stick to your pup’s routine, follow your instructions, and make sure they get plenty of attention and belly rubs. Plus, I keep you in the loop with updates so you can relax knowing your furry best friend is in great hands!

“The visit photos showed that my shy cats were happy to play with Kai. And even though it was a last-minute holiday booking, Kai worked around my schedule to promptly get and return my keys. I would definitely welcome her into my home to care for my cats again.”

Erin C.

“Zoe took great care of my cat while I was out of town. She was always so fast to respond, and very punctual. She sent lots of pictures from her visit and let me know how he was doing. I would definitely book with her again!”

Teresa B.