House Sitting In Near South Side Chicago
Find a loving house sitter to watch over your pets and your home.

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Top rated Near South Side house sitters

“Emily housesat for me and watched my cat on short notice for 5 days. My cat has anxiety, takes medication, and requires a lot of attention, so I was very pleased when my cat Pumpkin seemed to really bond with Emily and felt comfortable around her. I have never left Pumpkin alone before due to his anxiety (and my own!) and I felt so much better knowing Pumpkin was taken care of. Emily sent lots of updates which assured me Pumpkin was happy, and even cleaned sheets and towels she used before the end of the housesitting. Additionally, Emily was able to accommodate a last minute extension due to some travel issues on my part. I would book Emily again, and trust her to take great care of my boy!”


“Brianna is so amazing, would 100% recommend her to take care of your pet! She is so kind and asked many great questions about our pet and home at our meet and greet. She took care of our dog for over two weeks and sent daily pictures and updates. She played with him, took him on long walks and brushed him. Our dog clearly loved her and her communication made us feel so reassured on our trip! She also left our place very clean. We are so lucky to have found her!”


“Nia is great! She took wonderful care of my elderly cat and dog while I was traveling for the holidays. I received plenty up pictures and check-in updates. I was very at ease knowing my pets were being cared for by Nia. I would absolutely trust Nia to watch my pets again.”


“We were glad to have Alison sit Wrigley in our home for a few days - Alison is communicative, responsible and tidy! Photos throughout the visit verified Wrigley felt super comfortable and we’d be glad to have Alison back again!”


“Tylisha was great at communicating our pup’s needs and kept us updated on our trip. She even came through when we needed to extend our trip. We would definitely love to have her watch Obi again.”



“Pablo was fantastic looking after our dog while we were on vacation. This is our first time using Rover and have anyone dog sitting in our home. We usually board our dog. This was a fantastic experience and Pablo was great. He sent lots of pics and videos and we could see our dog was very happy. Thanks Pablo!”


“Elizabeth and Quincy had a lovely connection from the moment they met! I felt so relieved knowing she was with him during my business trip. She took good care of my little guy and I’m so grateful.”


“Amanda left our place spotless and well cared for…but more importantly, our dogs seemed relaxed, happy, and clearly well cared for. Communication was great over the entire stay. Thank you Amanda!”



“Emily is great! She checked in often and took excellent care of Maeve and McKenna - we look forward to working with her again soon and will definitely recommend her to friends.”


“Chauntrell was great sitting my dog and cat over a week long trip. He sent multiple pictures every day and was very detailed. He even checked on routine and if certain behaviors were expected from the pets. My dog was sad to see him go!”


“Nicole was superb: friendly, prompt, communicative, and most of all, really great with our two puppies. They got more walks with her than they have in a very long time! She sent videos, photos, and updates each day, which we really appreciated. Will absolutely book her again.”


“Molly was wonderful! She has been great with communicating and responding back pretty quickly and sending updates. I could tell that my pup was well taken care of and that he was very relaxed. We booked with Molly again next month! Thank you, Molly!”


“Alyssa is literally a godsend. I get really anxious about leaving my two pups (a puppy and a senior), but Alyssa was so communicative and thorough that I felt comfortable every day of our 2-week vacation. Alyssa is responsible, always on-time, and organized. Our house looked exactly as we left it! And obviously, she clearly loves pets and ours love her. Highly recommend!!!”


“Mairead is an amazing sitter. She took such great care of my dog who had just gotten diagnosed with cancer. Another sitter cancelled on me with 18 hours’ notice. I reached out to Mairead and she swooped in like Superman. I couldn’t be more grateful. She was diligent and communicative. Look no further than Mairead for all your sitting needs.”


“Bella did a fabulous job taking care of my dog Buster. Buster is an elderly dog and he is cautious with new people. Bella was patient with him and followed his lead until Buster felt comfortable with her.”


“Grace took amazing care of our dogo, Wizard, while staying in our home. She was incredibly respectful of our space, very responsive, always on time, and just generally awesome to work with. We came home to a happy pup and a spotless house. Highly recommend her!”


“Connie is fantastic! Excellent communication and took great care of my pets (cat and senior pit bull). My animals absolutely adore her and have already requested that she stays with them again :)”

Loving house sitters in your neighborhood
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Emily P.Star Sitter

“Emily housesat for me and watched my cat on short notice for 5 days. My cat has anxiety, takes medication, and requires a lot of attention, so I was very pleased when my cat Pumpkin seemed to really bond with Emily and felt comfortable around her. I have never left Pumpkin alone before due to his anxiety (and my own!) and I felt so much better knowing Pumpkin was taken care of. Emily sent lots of updates which assured me Pumpkin was happy, and even cleaned sheets and towels she used before the end of the housesitting. Additionally, Emily was able to accommodate a last minute extension due to some travel issues on my part. I would book Emily again, and trust her to take great care of my boy!”


Brianna J.Star Sitter

“Brianna is so amazing, would 100% recommend her to take care of your pet! She is so kind and asked many great questions about our pet and home at our meet and greet. She took care of our dog for over two weeks and sent daily pictures and updates. She played with him, took him on long walks and brushed him. Our dog clearly loved her and her communication made us feel so reassured on our trip! She also left our place very clean. We are so lucky to have found her!”


Nia A.
Star Sitter


“Nia is great! She took wonderful care of my elderly cat and dog while I was traveling for the holidays. I received plenty up pictures and check-in updates. I was very at ease knowing my pets were being cared for by Nia. I would absolutely trust Nia to watch my pets again.”


Alison F.Star Sitter

“We were glad to have Alison sit Wrigley in our home for a few days - Alison is communicative, responsible and tidy! Photos throughout the visit verified Wrigley felt super comfortable and we’d be glad to have Alison back again!”


Tylisha J.Star Sitter

“Tylisha was great at communicating our pup’s needs and kept us updated on our trip. She even came through when we needed to extend our trip. We would definitely love to have her watch Obi again.”




Pablo V.
Star Sitter


“Pablo was fantastic looking after our dog while we were on vacation. This is our first time using Rover and have anyone dog sitting in our home. We usually board our dog. This was a fantastic experience and Pablo was great. He sent lots of pics and videos and we could see our dog was very happy. Thanks Pablo!”


Elizabeth C.
Star Sitter


“Elizabeth and Quincy had a lovely connection from the moment they met! I felt so relieved knowing she was with him during my business trip. She took good care of my little guy and I’m so grateful.”


Amanda B.

“Amanda left our place spotless and well cared for…but more importantly, our dogs seemed relaxed, happy, and clearly well cared for. Communication was great over the entire stay. Thank you Amanda!”




Emily N.Star Sitter

“Emily is great! She checked in often and took excellent care of Maeve and McKenna - we look forward to working with her again soon and will definitely recommend her to friends.”


Chauntrell W.

“Chauntrell was great sitting my dog and cat over a week long trip. He sent multiple pictures every day and was very detailed. He even checked on routine and if certain behaviors were expected from the pets. My dog was sad to see him go!”


Nicole R.

“Nicole was superb: friendly, prompt, communicative, and most of all, really great with our two puppies. They got more walks with her than they have in a very long time! She sent videos, photos, and updates each day, which we really appreciated. Will absolutely book her again.”


molly m.

“Molly was wonderful! She has been great with communicating and responding back pretty quickly and sending updates. I could tell that my pup was well taken care of and that he was very relaxed. We booked with Molly again next month! Thank you, Molly!”


Alysia G.

“Always a pleasure to have Alysia pet sit/house sit for us.”




Allison J.

“Second time using Allison, she takes great care of our two cats, left our home pristine, and even watered our plants! Allison is great with the guys!”


Alyssa G.Star Sitter

“Alyssa is literally a godsend. I get really anxious about leaving my two pups (a puppy and a senior), but Alyssa was so communicative and thorough that I felt comfortable every day of our 2-week vacation. Alyssa is responsible, always on-time, and organized. Our house looked exactly as we left it! And obviously, she clearly loves pets and ours love her. Highly recommend!!!”


Mairead M.

“Mairead is an amazing sitter. She took such great care of my dog who had just gotten diagnosed with cancer. Another sitter cancelled on me with 18 hours’ notice. I reached out to Mairead and she swooped in like Superman. I couldn’t be more grateful. She was diligent and communicative. Look no further than Mairead for all your sitting needs.”


Bella B.

“Bella did a fabulous job taking care of my dog Buster. Buster is an elderly dog and he is cautious with new people. Bella was patient with him and followed his lead until Buster felt comfortable with her.”


Johnathan W.Star Sitter

“Johnathan is great! Our dog felt immediately comfortable with him and they had a great time together. He was communicative and really great all around.”


Grace R.

“Grace took amazing care of our dogo, Wizard, while staying in our home. She was incredibly respectful of our space, very responsive, always on time, and just generally awesome to work with. We came home to a happy pup and a spotless house. Highly recommend her!”


Connie C.

“Connie is fantastic! Excellent communication and took great care of my pets (cat and senior pit bull). My animals absolutely adore her and have already requested that she stays with them again :)”
How Rover works
1. Search
Read verified reviews and choose a house sitter who’s a great match for you and your pets2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away3. 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 house 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.
House Sitting FAQs
Frequently asked questions about Rover
House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Near South Side on Rover as of Aug 2025 was about $50 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.
Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 91% of Near South Side house sitters respond in under an hour.
Experience can vary widely from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when comparing house sitters available in Near South Side.
Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Near South Side house sitters are great for:
- Dogs who’d prefer to stay on their home turf
- Cats and caged pets
- Pet parents on a tight schedule
- Keeping an eye on your home and plants while you’re away
Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house 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 house 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 house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.
