Pet Sitting & Drop Ins In Near South Side Chicago
Book a pet sitter to stop by your home a few times a day to feed and play with your pet.

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Top rated Near South Side pet sitters
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

“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!”

“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.”

“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.”

“Anthony had a calm approach with our dogs … which was important to us. They are “new” to the city life … so we always wonder what might trigger them. And if a “new” person walking them would make them act differently. Anthony even paid attention to the details like a special lock we have on the door. And fed our pups treats at the end. It was a good experience.”

“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.”

“Continues to be my favorite sitter. Super reliable and communicative. David clearly cares about all animals and totally understands a person’s love for their pets and always sends detailed updates! Will definitely be contacting David again!”

“Rachel was beyond the perfect choice for watching our Eevee (cat) while we were gone! I would recommend her 10/10 times. She went above and beyond and made me feel at ease!”

“Isabel was the greatest! We are so lucky to have found her- especially since it was less than 24 hour notice. She sent awesome photos and our puppy got all his wiggles out walking and playing with her. She really goes the extra mile to form not only a connection with our puppy, but also us as owners. I highly recommend working with Isabel, and hope we get the chance to work with her again soon (and so does our pup!)!”

“This was Namira's second time watching my elderly dog, who added two pills since our last visit, and has been starting to struggle with joints. She was engaged and made sure to check in with me when he was potentially having a bad day so I could evaluate and I could feel confident he was in good hands once again.”


“Madison is a terrific sitter for my Ragdoll cat! She’s kind and very thoughtful and is someone who is very dependable. She goes the “extra mile” to help me out! I highly recommend her to care for your pet!”


“This was the first time Sandra did a drop-in visit for my cats and she was wonderful. She messaged me lots of photos and gave very detailed notes about her visit, gave my older cat her medication chew and younger cat her dental treat, and did everything as asked. Both of my cats seemed to really love her. Thanks, Sandra! :)”

“Karolly was a lifesaver!! She took amazing care of our cat during the holidays and alerted us of an issue that had occurred at our home while we were away - she saved our home from major damage! Beyond that, from her first visit, our cat immediately took to her. She took great care of him and sent us pictures and video from her visit, he looked like he was having a great time! She fed him treats, gave him plenty of belly rubs, and played with his toys with him. We look forward for having her care for our pets again in the future!”

“Great walker! Very reliable, punctual, and caring. My dog was happy and well taken care of, and I really appreciated the updates and photos during the walk. You can tell they genuinely love animals and treat them with care. I would definitely book again and highly recommend!”

“We were hesitant to try Rover again after a not-so-great experience with another sitter, but Emily completely changed our minds. She treated our cat like she was her own, with so much care and attention. We had a couple of specific requests, and she was super professional, flexible, and understanding. She also respected our home and even cleaned up more than we expected, which was such a nice surprise. We honestly can’t thank Emily enough for giving us peace of mind while we were away. Our cat was so happy and well taken care of. We’d 100% recommend her to anyone and will definitely book with her again.”


“Alexa was kind, professional, and wonderful with our puppy! We felt very comfortable leaving him with a sitter for the first time and he enjoyed spending the morning with her. Alexa was perfect at every step of the process!”

“morgan rocks!! she took great care of my cat, sent lots of photos & updates, and even vacuumed before leaving so i could come home to a clean house and happy kitty :)”

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
Near South Side pet parents share their Rover experiences
Andres dropped in on our two cats for a long weekend while we were out of town. He was an amazing rover! Very communicative, reliable, and easy to work with. I could tell our cars were very happy with his companionship. I definitely plan to book again and highly recommend hom to anyone looking for pet care!

Lily is a fantastic and reliable sitter! My cat has a great time with her during their visits, and Lily always makes sure to send detailed updates on how things are going and lots of pictures. I would definitely work with Lily again in the future for any pet sitting needs!

Popular requests near you
Select a filter and find qualifying Near South Side sitters!How Rover works

1. Search
Read verified reviews by pet parents like you and choose a sitter who’s a great match for you and your pets
2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your pets while you’re away
3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
Why Choose Rover?
Cashless payments
Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn’t happen often, but if your pet sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
Pet Sitting FAQs
Frequently asked questions about Rover
Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, pet sitters on Rover respond in under an hour.
Experience can vary widely from pet sitter to pet sitter, but you can view reviews, years of experience, and number of repeat clients when comparing pet sitters available in Near South Side.
Rover makes it easy to find Near South Side pet sitters to provide loving care from their own home. The background-checked, 5-star pet sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet sitting is great for:
- Pets of all ages and abilities, including puppies
- Pet parents looking for a safe, loving alternative to a kennel
- Pets who’d love to socialize with their pet sitter’s pets
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your pet sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your pet sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your pet sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your pet service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.






















