House Sitting Near South Side

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Over 353
pet parents in Near South Side have booked house sitting

Near South Side, Find top rated house sitting

Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

1 / 1
Sitter Profile Image: Chloe K.
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Chloe K.
from
$50
per night
5.0 out of 5 stars
7 reviews
2 repeat clients
10 years of experience
Near South Side, Chicgao, IL, 60616

Chloe is AMAZING; she took such great care of my boy. He was happy when I got home, so I knew he liked her too. I got fantastic updates, which made me feel at ease.

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Kay T.
Sitter Profile Image: Emily N.
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Emily N.
Star Sitter
from
$68
per night
5.0 out of 5 stars
238 reviews
66 repeat clients
10 years of experience
Chicago, IL, 60605

I was very nervous as a first time Rover user and so happy I found Emily! She asked detailed questions about my dogs care and habits during our initial meet and greet which put me at ease, sent photo updates during her stay where he seemed very happy / comfortable with her and came home to a clean place. Would definitely book again!

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Shannon S.
Sitter Profile Image: Elizabeth C.
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Elizabeth C.
from
$75
per night
5.0 out of 5 stars
57 reviews
22 repeat clients
10 years of experience
Loop, Chicago, IL, 60601

Elizabeth was awesome! We have already booked her for an additional four stays! One of our pups isn't very trusting and tends to bark and lunge at new people. When Elizabeth came to meet them, she didn't even flinch. She remained calm and let Kona get adjusted which is exactly what Kona needed to feel comfortable. Elizabeth also sent us updates with photos of our pups while we were gone. We don't have kids, so our dogs are our kids and we, understandably, felt nervous leaving them with a new person. However, we felt so comfortable with Elizabeth and look forward to having her stay again in the future.

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Alex S.
Sitter Profile Image: Anastasiia M.
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Anastasiia M.
Star Sitter
from
$75
per night
5.0 out of 5 stars
174 reviews
40 repeat clients
17 years of experience
Chicago, IL, 60601

Anastasiia was wonderful with our 8yo lab mix! She agreed to stay with her on VERY short notice, and she was professional & super communicative. We so appreciated it & will DEFINITELY use her again!

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Brannon W.
Sitter Profile Image: Eliana B.
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Eliana B.
from
$55
per night
5.0 out of 5 stars
5 reviews
3 years of experience
Lower West Side, Chicago, IL, 60608

Eliana was absolutely amazing. My partner and I have a disabled fur baby with a number of special needs, and Eliana was incredibly diligent, asked all the right questions, followed our instructions closely, and took such great care of Miss Bean and our home. We came home to a happy, healthy pup and couldn’t have been more appreciative. I will absolutely be reaching back out for future travel plans. She was a dream to have stay with our fur baby!

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William R.
Sitter Profile Image: Samantha E.
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Samantha E.
Star Sitter
from
$40
per night
5.0 out of 5 stars
144 reviews
62 repeat clients
13 years of experience
Loop, Chicago, IL, 60602

Samantha is amazing. She took care of my two Frenchies for 8 days in my home. She took over new training techniques for the puppy with no problem (with very little notice I might add). She took amazing care of my babes and left my apartment just as I’d left it. Love her!

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C A.
Sitter Profile Image: Elizabeth A.
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Elizabeth A.
from
$40
per night
5.0 out of 5 stars
10 reviews
2 repeat clients
12 years of experience
Chicago, IL, 60607

Great communication and my pup loved hanging out with Elizabeth!

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Jake R.
Sitter Profile Image: Jorie S.
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Jorie S.
from
$70
per night
5.0 out of 5 stars
19 reviews
8 repeat clients
15 years of experience
Chicago, IL, 60605

Jorie was great with my anxious dog Bear! She was patient, calm, and gently assertive where needed and he felt very comfortable with her. He can be reactive with strangers and she handled him well. Bear fell into his normal routine quickly, and relaxed at home during the house sit.

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Sindhu S.
Sitter Profile Image: Cheyanne H.
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Cheyanne H.
Star Sitter
from
$36
per night
5.0 out of 5 stars
32 reviews
24 repeat clients
10 years of experience
Near South Side, Chicago, IL, 60616

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.

Sitter Profile Image: Faith M.
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Faith M.
from
$60
per night
5.0 out of 5 stars
20 reviews
9 repeat clients
10 years of experience
Chicago, IL, 60622

Faith showed up for every drop in and took my babies for walks. She kept an extra close eye on Neville because he’d just had a tooth extracted and was on a soft diet with pain meds. Faith patiently soaked his kibble and proportioned his wet food to go with it and I’m so grateful for that. She was great with my fur children.

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Marissa G.
Sitter Profile Image: Erin K.
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Erin K.
from
$60
per night
5.0 out of 5 stars
6 reviews
1 repeat client
25 years of experience
Near South Side, Chicago, IL, 60612

Erin is amazing! While we were vacationing in Chicago she came to our hotel room to watch our 2 Wheaties. Erin was punctual, professional, friendly, and wonderful with our dogs. She even sent us pics and kept us updated on the dogs’ status. The situation was not ideal in a hotel room but Erin was completely understanding and accommodating. ABSOLUTELY RECOMMEND!!!

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Shannon B.
Sitter Profile Image: Angela E.
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Angela E.
Star Sitter
from
$75
per night
5.0 out of 5 stars
67 reviews
5 repeat clients
5 years of experience
Lower West Side, Chicago, IL, 60616

Angela was amazing with George and was able to help us out when we came to town for the night. She’s extremely knowledgeable, kind and timely. Can’t recommend her enough!

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Dalara & Jack F.
Sitter Profile Image: Katie "Anni" W.
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Katie "Anni" W.
Star Sitter
from
$70
per night
5.0 out of 5 stars
106 reviews
31 repeat clients
10 years of experience
Near South Side, Chicago, IL, 60616

Anni was amazing with our two dogs! She truly went above and beyond for their care—even taking a trip to the vet to pick up medication for our anxious dog. She was so patient and kind with them, I cannot think of anyone taking better care of them in our absence. Cannot recommend more!

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Courtney M.
Sitter Profile Image: Tylisha J.
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Tylisha J.
from
$45
per night
4.9 out of 5 stars
41 reviews
10 repeat clients
3 years of experience
Chicago, IL, 60605

Tylisha was great! Very responsive, prompt, lots of photos shared and Airlie seemed very happy when I got home. House was clean and tidy. Highly recommend!

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Dane C.
Sitter Profile Image: Shannon S.
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Shannon S.
from
$60
per night
20 years of experience
Chicago, IL, 60605

About: I grew up with all sorts of pets - hamsters, guinea pigs, cats, and my childhood English lab, Sprocket. As a kid I watched my neighbors' cats and walked their dogs, I also cat sat while I lived abroad in Korea before my husband and I finally adopted our own rescue dog, Charlie! I'm self-employed and have a flexible schedule. Since I have Charlie at home I can't offer boarding, but I'd love to care for your pet in the comfort of your home! I'm extremely active, so your dog will not be going without walks! I have dog sat off the Rover platform and am happy to share that reference. I have experience with dogs of all sizes and exercise needs. I'm able to administer medication and have experience with anxious dogs (thanks, Charlie!) Would love to set up a meet and greet to get to know each other and your pet's needs! I'm a realtor so my schedule looks different every day, but when I'm not hopping around the city I'm working from home. I am able to commit to stays up to one week long max for now. If you're a new client, it'd be great to get to know each other with a shorter stay first, or at least a meet and greet at your home! I want to make sure your pet is as familiar and comfortable with me as possible before your trip, so you can fully relax. Whatever instructions you give me, I'll follow! Let's talk ahead of time about your pets quirks and needs - as a dog owner myself I completely understand the anxiety of leaving your pet in someone else's care, especially since my dog has her own set of special needs! My goal is to replicate how you care for your own pet as closely as possible. I'm extremely detail-oriented and will keep your home as clean as you left it. I would love to be that trusted person you come back to any time you need a petsitter!

Sitter Profile Image: Jessica S.
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Jessica S.
Star Sitter
from
$60
per night
5.0 out of 5 stars
40 reviews
15 repeat clients
5 years of experience
Near West Side, Chicago, IL, 60607

Took amazing care of our dogs while we were away for 10 days! She kept us up to date regularly and took some of the best pictures. She also got them comfortable with short outdoor walks which we plan to keep up now that we’re back. Would highly recommend her for your pet care needs !

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Lawrence L.
Sitter Profile Image: Nadine T.
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Nadine T.
Star Sitter
from
$70
per night
5.0 out of 5 stars
56 reviews
14 repeat clients
15 years of experience
Near South Side, Chicago, IL, 60616

Nadine house sat our 7-year-old pup during a five-day trip and took great care of her! She is great and very affectionate with dogs; my sheepadoodle instantly warmed up to her during our meet and greet. She was very communicative and sent many updates and lovely photos, which really put us at ease while away. I would definitely recommend Nadine!

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Querida Q.
Sitter Profile Image: Elissa M.
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Elissa M.
Star Sitter
from
$80
per night
5.0 out of 5 stars
46 reviews
23 repeat clients
15 years of experience
Chicago, IL, 60642

Elissa was so amazing with our pup, Lincoln! She gave regular updates and photos and was also so flexible when our travel was a little delayed. I felt so comfortable the entire visit - I can’t thank her enough!

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Eliza & Rob B.
Sitter Profile Image: Kieanji W.
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Kieanji W.
Star Sitter
from
$25
per night
4.9 out of 5 stars
28 reviews
2 repeat clients
20 years of experience
Chicago, IL, 60604

Kieanji is a great dogsitter! She was very patient with my anxious dog, asked good questions to help him feel comfortable, sent pictures, and was very responsive. Both times she dogsat my dog she arrived on time and tidied up before she left. Would definitely recommend! Kieanji!

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Jacqueline M.
Sitter Profile Image: Elizabeth D.
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Elizabeth D.
from
$45
per night
5.0 out of 5 stars
32 reviews
9 repeat clients
20 years of experience
Chicago, IL, 60609

Elizabeth is always so great with my dog! I really appreciate the consistent pictures and updates while I’m gone, it really puts my mind at ease. This is my second time having her house sit and both times have been amazing!

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Kennedy C.
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The median cost per night for house sitting in Near South Side is $50

Pet parents share their Rover experiences - Near South Side

1 / 1
5.0 out of 5 stars

Zhanna was absolutely amazing with my cat, who is an Abyssinian cat. He can definitely be a handful, he’s extremely curious, energetic, and very demanding when it comes to attention but she handled him perfectly. She was patient, attentive, and genuinely engaged with him, and I could tell he felt completely comfortable with her. I really appreciated the updates and knowing he was getting plenty of attention and affection while I was away. I felt completely at ease leaving him in her care and would absolutely book with Zhanna again!

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Iryna K.
House Sitting
5.0 out of 5 stars

Allison was absolutely wonderful with our French bulldog and two cats. As protective pet parents, this was our first time leaving all three of them in someone else’s care, so naturally we were a little apprehensive. Allison immediately put us at ease by offering two consultation visits before our trip so she could thoroughly understand our pets’ individual needs, routines, personalities, and home environment. That level of preparation and genuine care meant a lot to us. Throughout our vacation, Allison was incredibly attentive and responsive. She arrived early and kept us updated with multiple messages and plenty of photos, which gave us so much peace of mind while we were away. It was clear that she wasn’t simply checking in on our pets, but genuinely caring for them and making sure they were happy and comfortable. She even went above and beyond by offering thoughtful advice for our continued care of the pets, which we really appreciated. You can tell Allison truly loves animals and takes the responsibility of caring for them seriously. She also left the house tidy and in great shape. It was such a small gesture, but after coming home from a long trip, walking into a clean and tidy home made a bigger difference than she probably realized. We came home to three happy, well-cared-for pets and felt completely comfortable knowing they were in Allison’s hands. She helped make our vacation so much more enjoyable because we never had to worry about how things were going at home. We would absolutely recommend Allison and will definitely be using her services again. Thank you, Allison, for taking such wonderful care of our babies and allowing us to have such a relaxing vacation. We truly couldn’t have done it without you!

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Danny R.
House Sitting
5.0 out of 5 stars

Natalie was great and highly recommend! She was so caring and attentive, and sent us regular updates to keep us in the know. Natalie made it incredibly easy and our dog absolutely adored her!

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Bennett E.
House Sitting
5.0 out of 5 stars

Vaughan did an excellent job with our senior German Shepherd. Great at administering meds and communication. We will be rebooking!

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Heather E.
House Sitting
5.0 out of 5 stars

Meg took great care of my dog for an extended weekend. She was super communicative all weekend which made me feel like my dog was in great hands!

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Krista M.
House Sitting
5.0 out of 5 stars

Elizabeth was a great sitter! She was communicative, provided consistent updates, and followed Momo’s usual routine. We would definitely use her again.

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Melissa A.
House Sitting
5.0 out of 5 stars

Emily and Fran took such good care of Benny! They are great about communicating and sending updates. I could tell Benny was happy and content while with them. I will definitely use them again!!!

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Margarita R.
House Sitting
5.0 out of 5 stars

Eliana was absolutely amazing. My partner and I have a disabled fur baby with a number of special needs, and Eliana was incredibly diligent, asked all the right questions, followed our instructions closely, and took such great care of Miss Bean and our home. We came home to a happy, healthy pup and couldn’t have been more appreciative. I will absolutely be reaching back out for future travel plans. She was a dream to have stay with our fur baby!

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William R.
House Sitting
5.0 out of 5 stars

Nicole was great with my senior dog, Bella, while I was away for a long weekend. She sent tons of updates, was a great communicator & left my place nice and clean. I fully trusted Bella was in great hands with her and well taken care of. Highly recommend!!

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Tiffany B.
House Sitting
5.0 out of 5 stars

Morgan was absolutely fantastic and cannot recommend her highly enough. Our pup is a senior with some special needs and she took great care of him and kept us updated throughout the stay. Home was in perfect condition and she went above and beyond in cleaning up and making it brand new. Morgan is the best!

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Conner G.
House Sitting
5.0 out of 5 stars

Danielle was amazing with my dogs! She was very patient, caring, and attentive to their needs. She kept me updated throughout their stay and sent plenty of pictures, which gave me great peace of mind. It was clear they were happy and well cared for. I highly recommend Danielle and will definitely use her again!

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Jerónimo Á.
House Sitting
5.0 out of 5 stars

McKenzie is a stellar house sitter - she sent me daily updates about my pets while I was out of town and we both cheered when my very shy cats came out of hiding for her! She also left my home in spotless condition. I will absolutely book again for future travel. Thank you McKenzie!

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Sadie K.
House Sitting
5.0 out of 5 stars

Repeat clients of Kaitlyn and most recently had her stay in our home while in Europe for 10 days. Kaitlyn is reliable, trustworthy, communicative and very respectful of our space. Our pup loves her!

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Allie M.
House Sitting
5.0 out of 5 stars

Maggie was amazing! I have a high-anxiety senior dog that requires lots of meds and instructions. She followed everything perfectly and gave many pictures and updates. I know my dog felt comfortable with her and I would definitely book her again!

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Lauryn S.
House Sitting
5.0 out of 5 stars

Angelina took amazing care of our pup, sent lots of photos and updates, and left our house in perfect condition. Would highly recommend her as a sitter!

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Cassie W.
House Sitting
5.0 out of 5 stars

Alli is remarkable! She made our trip worry free! She bonded quickly with our Blue Heeler so quickly which doesn’t happen easily. We can’t thank her enough and will absolutely be working with her every time we go out of town!

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Colby H.
House Sitting
5.0 out of 5 stars

Dominick ROCKS! This was our first time leaving our baby for this long and she made it so easy. Clean, communicative, kind, and reliable!!!

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Hallie P.
House Sitting
5.0 out of 5 stars

Amber was fantastic! Super accommodating and easy to work with, plus my pup thought she was great! :)

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Jamie M.
House Sitting
5.0 out of 5 stars

Linh is incredible! She has helped me troubleshoot technical issues with my cat’s feeder and litter box. She is super communicative and makes my life easy!

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Kelsie M.
House Sitting
5.0 out of 5 stars

We trusted Ann-Marie to care for our toy fox terrier Loki in our house for over a week. She did a wonderful job! When we got home, it was clear that Loki adores her—he was happy, relaxed, and sad to see her go. Ann-Marie adjusted perfectly to Loki’s schedule and sent us photos while we were away. She even took him on walks to new places that he loved. Most of all, Ann-Marie was a calm, reliable and trustworthy presence in Loki’s life for an extended period of time. We are extremely grateful. Thank you so much!!!

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Maria M.
House Sitting
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