Pet Sitting & Drop Ins In Near South Side Chicago

“Hallie did a great job on a last minute request. She provided great updates about my girls and even let me know that my sink wasn’t draining! I will definitely book with her again.”

Sarah B.

“Eunice went above and beyond with my Tev! She came back the second day even though Tevi was having a hard time during the first visit. Eunice was amazing and very communicative.”

Ally R.

About: Up until recently I had a large reactive dog. She was my best friend and taught me not only patience, but also taught me so much about dogs. I wfh and am looking to add a little something to my schedule. I would love to give your dog the exercise it needs while you’re at work. I am willing to work with reactive dogs in case by case basis. I am also a dog walking volunteer at CACC. I wfh and have flexibility in my schedule. I am available afternoons and evenings m-f and can work something out on weekends if it was needed. I would take care of your animals at your home based on instructions you give me for you pet. I respect you as an owner and your pet and do not want to give overstep and boundaries

“Nadine was great! She was patient with my sassy cat and very communicative with me while I was on vacation. Would definitely use Nadine in the future.”

Stephanie D.

“I love getting to see the little report card for the pups and the clear joy on their faces! Jason is always amazing and punctual and as a project manager I appreciate that he never needs me to check in to make sure he’s tracking for the occasional visits that I schedule well in advance. So amazing!”

Sarah S.

“Anthony was great with Bella! He was responsive, sent photos, and always kept me updated with everything. I highly recommend booking with Anthony, I know I will in the future.”

Denyse J.

“Isabel is awesome and very consistent. My dog gets a little anxious at times and she established a routine that he absolutely loves. Highly recommend!”

Gracelyn F.

“We are so grateful for Sandra! We have booked multiple times and she always provides great care and attention for our cat. She is a excellent and frequent communicator and we will definitely rebook in the future.”

Margo B.

“She’s amazing! We always get the most thorough report card for our two babies and she recently watched both of our cats for a week while we were out of the country and she arrived twice a day at the time we requested and sent lots of pics and played with our fur babies in the most fun and loving way! We felt 100% at ease having her here and that our cats were well taken care of! Forgot to mention one of our cats is senior and needs meds and lots of love and she was always in amazing shape and cared for when we returned…not stressed at all, which never happens after long times away! We will continue to use Julianne and are so grateful for her!”

Rachael E.

“David was extremely communicative and understanding about my pets’ needs. Very easy to coordinate with and respectful of my space and my request for plenty of pictures :) I will absolutely be booking with David again!”

Sarah L.

“Rachel was amazing and attentive checking in on my two cats! After having a previous sitter cancel on me last minute, Rachel saved the day being available at very short notice. She went above and beyond making sure that my boys had human company and were comfortable whilst I was out of town.”

Axel G.

“Jason is absolutely INCREDIBLE with my two cat gals. He plays with them when they are missing me and is SO accommodating. I trust Jason with my fur babies and always reach out to him first if I am out of town. Tomato and Elphie love you, Jason! Thanks for being amazing.”

Abby D.

“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.

About: I have a special place in my heart for senior care, having cared for my friend's paralyzed pup and my own dog had dementia for 2 years, so I understand how hard it is to be put in a situation to have to leave your pet in such crucial years. I've been with dogs of all ages and sizes though and am normally the "go-to" trusted person out of all my friends to care for their pets. I work hybrid - full time 9-5 hours but also have flexibility in my schedule to give care to your pet and attention to their specific needs. In both my home and/or my clients' homes, I want to ensure pets feel safe, and comfortable by creating a calm environment and following their individual routines. I also will want to communicate to you, the client, often as well to make sure wherever you are you can feel comfortable your pet is well cared for.

“Morgan went above and beyond when my cats somehow managed to shatter a glass table. She also took great care of the kitties and was punctual and communicative. Thanks Morgan!”

Jeffrey S. R.

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.

“Daphnay was amazing! She was always on time for twice daily check-ins. She played with Bleu as well as took him on runs. She is really reliable and very trustworthy. Can’t wait to book her again.”

Eric T.

“Emily has been fantastic! I feel safe leaving my boys with her. She's reliable, responsible, plays with them and takes great pictures! HIGHLY recommend!”

Vincenta L.

About: "I prefer dogs over humans" - I have grown up with dogs and rescued plenty pups in India. Currently I have my baby (Daisy) who holds all my heart! My dream is to set up a dog boarding which sustains a rescue of Chicago animal care and control long term dogs ( the ones often forgotten ) and this is my 1st step to that that leap. I have dog sat my friends dogs in the neighborhood and I know I will be a responsible trusted partner for any dog parent. I understand the stress of leaving your pup behind that why my commitment is to relive your stess by providing a reliable experience to your babies and you! I don't board more than 1 dog at a time and I provide as many updates as I can 💕 and as many as you may prefer!! I am available over the week ( Thursday to Monday ) and I work from home so I can flexiblely manage my schedule and take care of the walks play time etc. My pup is shy and friendly . As this would be a new set up for her, I always insist on a meet and greet with me and my puppy outside first before accepting your booking.

About: I’ve cared for my own dog, Scoresby, for over ten years, and in that time I’ve also looked after many friends’ dogs: everything from energetic puppies to gentle seniors. Living with and caring for dogs has taught me patience, consistency, and how to read each dog’s unique personality and needs. I’m comfortable with all kinds of dogs and take pride in creating a calm, structured environment that helps them feel secure and happy. I pay attention to details: whether it’s sticking to a feeding schedule, managing medications, or giving extra time and care to older dogs. With my creative, flexible work-from-home schedule, I’m able to give dogs plenty of one-on-one attention, long walks, and genuine companionship throughout the day. I’m an artist, writer, and researcher who works from my home studio here in the South Loop. My days are filled with creativity, curiosity, and good company, especially from my own dog, Scoresby. He and I explore the neighborhood together every day, taking four walks to a variety of parks and scenic spots around the area. Caring for dogs has become a natural part of my daily rhythm. I understand how much our pets mean to us, and I bring that same sense of attention, reliability, and affection to every dog I look after. Whether it’s long walks, quiet companionship, or keeping to a specific routine, I make sure each pup feels safe, happy, and cared for—just like my own. I live in a spacious, dog-friendly loft apartment right across the street from 16th & Prairie Dog Park, with Fred Anderson Dog Friendly Area and Prairie District Park just a short walk away. My home has plenty of open space and a calm, creative atmosphere where dogs can relax and feel comfortable. I take safety and routine seriously. Dogs are always supervised, and I make sure they’re securely leashed during walks and when entering or leaving the building. My own dog, Scoresby, is friendly and well-socialized, and he enjoys having other dogs join us for our daily walks, covering at least 2 miles a day through different parks and routes in the South Loop. Whether a pup is staying with me or I’m visiting them in their own home, I focus on creating a consistent, caring environment. I follow each dog’s routine closely (meals, walks, playtime, and rest) so they always feel secure and cared for, just as they would with their family.