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.

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Sitter Profile Image: Jason C.
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Jason C.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
159 reviews
33 repeat clients
10 years of experience
Near South Side, Chicago, IL, 60616

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!

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Sarah S.
Sitter Profile Image: Nadine T.
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Nadine T.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
33 reviews
7 repeat clients
15 years of experience
Near South Side, Chicago, IL, 60616

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.

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Stephanie D.
Sitter Profile Image: Hallie B.
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Hallie B.
from
$17
per visit
5.0 out of 5 stars
29 reviews
6 repeat clients
5 years of experience
Near South Side, Chicago, IL, 60605

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.

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Sarah B.
Sitter Profile Image: Anthony M.
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Anthony M.
Star Sitter
from
$21
per visit
5.0 out of 5 stars
513 reviews
60 repeat clients
25 years of experience
Near South Side, Chicago, IL, 60616

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.

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L B.
Sitter Profile Image: Eunice Y.
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Eunice Y.
Star Sitter
from
$22
per visit
5.0 out of 5 stars
59 reviews
27 repeat clients
4 years of experience
Loop, Chicago, IL, 60607

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.

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Ally R.
Sitter Profile Image: David K.
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David K.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
154 reviews
48 repeat clients
25 years of experience
Near South Side, Chicago, IL, 60616

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!

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Sarah L.
Sitter Profile Image: Rachel S.
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Rachel S.
from
$26
per visit
5.0 out of 5 stars
94 reviews
34 repeat clients
15 years of experience
Loop, Chicago, IL, 60605

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!

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Alyssa V.
Sitter Profile Image: Isabel K.
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Isabel K.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
12 reviews
4 repeat clients
2 years of experience
Loop, Chicago, IL, 60605

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!)!

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Laryssa O.
Sitter Profile Image: Namira J.
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Namira J.
Star Sitter
from
$19
per visit
4.9 out of 5 stars
41 reviews
16 repeat clients
10 years of experience
Chicago, IL, 60616

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.

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Brittany E.
Sitter Profile Image: Jorie S.
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Jorie S.
from
$25
per visit
5.0 out of 5 stars
16 reviews
7 repeat clients
15 years of experience
Near South Side, Chicago, IL, 60605

Excellent. Jorie always send pictures and feedback. She is thorough and the cats like her. Appreciate that we can trust that the cats are in good hands.

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Sandra W.
Sitter Profile Image: Madison J.
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Madison J.
from
$22
per visit
5.0 out of 5 stars
20 reviews
10 repeat clients
5 years of experience
Near South Side, Chicago, IL, 60605

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!

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Donna M.
Sitter Profile Image: Sandra T.
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Sandra T.
from
$22
per visit
5.0 out of 5 stars
456 reviews
122 repeat clients
25 years of experience
Loop, Chicago, IL, 60602

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! :)

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Jennifer L.
Sitter Profile Image: Jason C.
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Jason C.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
57 reviews
17 repeat clients
15 years of experience
Chicago, IL, 60616

My pup always is sad to leave Jason! She loves when he walks, sits, plays, etc with her! If you need someone to trust with your dog, Jason is the guy!

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Nick S.
Sitter Profile Image: Karolly Z.
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Karolly Z.
Star Sitter
from
$29
per visit
5.0 out of 5 stars
80 reviews
25 repeat clients
4 years of experience
Near South Side, Chicago, IL, 60605

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!

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Sarah F.
Sitter Profile Image: Nataliia S.
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Nataliia S.
Star Sitter
from
$21
per visit
4.9 out of 5 stars
26 reviews
13 repeat clients
2 years of experience
Chicago, IL, 60608

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!

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Max K.
Sitter Profile Image: Emily A.
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Emily A.
Star Sitter
from
$27
per visit
5.0 out of 5 stars
250 reviews
84 repeat clients
10 years of experience
Near South Side, Chicago, IL, 60605

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.

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Sydney C.
Sitter Profile Image: Taylor L.
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Taylor L.
from
$17
per visit
5.0 out of 5 stars
12 reviews
3 repeat clients
10 years of experience
Loop, Chicago, IL, 60605

Taylor went above and beyond, she was super kind and understanding of our dogs needs. She provided lots of updates and we felt assured that our pets were in safe hands!

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Adryanna S.
Sitter Profile Image: Alexa S.
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Alexa S.
from
$15
per visit
5.0 out of 5 stars
2 reviews
4 years of experience
Loop, Chicago, IL, 60605

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!

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Wesley D.
Sitter Profile Image: Morgan L.
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Morgan L.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
227 reviews
52 repeat clients
20 years of experience
Near West Side, Chicago, IL, 60606

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 :)

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Iman A.
Sitter Profile Image: Angela E.
Verified Enhanced Background Check
Angela E.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
53 reviews
3 repeat clients
5 years of experience
Lower West Side, Chicago, IL, 60616

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

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Near South Side pet parents share their Rover experiences

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5.0 out of 5 stars

Kayla was such a phenomenal sitter for my cat Albert! I highly recommend for attentive service and great care.

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Margaret P.
Drop-In Visits
5.0 out of 5 stars

Jean took excellent care of my two Kits !! I appreciate her knowledge, detailed communication and obvious concern for their comfort and wellbeing - Very trustworthy, very professional. Thank You Jean 🙏

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Holly M.
Drop-In Visits
5.0 out of 5 stars

Christine is the best cat sitter we’ve ever had. Our cats love her and she always sends lots of pictures and funny updates.

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Paige S.
Drop-In Visits
5.0 out of 5 stars

Sam took great care of my quite rambunctious 3 month old puppy and unfortunately gad to endure one of her bouts of zoomies. I would definitely recommend him.

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Jim M.
Drop-In Visits
5.0 out of 5 stars

Caroline was great!! Super communicative and immediately got along with my cat Todd. Good updates. Would definitely work with her again in the future!

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Travis R.
Drop-In Visits
5.0 out of 5 stars

Another great visit with Mia! Lots of photos and information during her visits giving lots of peace of mind.

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Emily C.
Drop-In Visits
5.0 out of 5 stars

Thank you again! I really appreciate the help with Percy, and the evidence from the cabinet thief. It’s a new apt, so that was actually good to know lol Hope to have you cat-sit for them again in the future!

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Alex B.
Drop-In Visits
5.0 out of 5 stars

Ruari was very responsive and sent photos to make certain to me that everything was good for our pet. Would recommend to anyone

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Will B.
Drop-In Visits
5.0 out of 5 stars

I had a last minute weekend trip and Vitaliia was great at getting back to me quick saying she can stop in and feed my cat! Great communication & quick response!

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Lindsey L.
Drop-In Visits
5.0 out of 5 stars

A gem of a person and my girls loved her. Very communicative and has a great vibe. Would definitely recommend!

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Leilani V.
Drop-In Visits
5.0 out of 5 stars

Christina did a great job taking care of my five cats, two of whom zi have medical needs. I really appreciated her daily updates and photos of my boys.

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Susan B.
Drop-In Visits
5.0 out of 5 stars

She was fantastic with our two shy cats. She was so careful and great with them that they warmed up to her by the end of the visits!

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Chris T.
Drop-In Visits
5.0 out of 5 stars

Stephanie was amazing and super attentive even during a major Chicago storm! She made sure our dog was safe and having the best time!

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molly b.
Drop-In Visits
5.0 out of 5 stars

Rachel was awesome! Extremely communicative and caring with our cat - I felt very connected and aware of what was going on. Rachel gives great, timely and detailed updates. I would 100% book with Rachel again!!

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Valentina F.
Drop-In Visits
5.0 out of 5 stars

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!

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Stella L.
Drop-In Visits
5.0 out of 5 stars

Always a pleasure booking with Cassi! She went above and beyond to make sure my kitty had enough litter. Always love the pics she sends in the report card too. Thanks Cassi!

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Mandy B.
Drop-In Visits
5.0 out of 5 stars

It was great having Nandini watch our kitty! She was on time everyday, played with the cat, took really good care of her and went above and beyond to take tons of pictures and videos for us! We'll definitely have her watch our cat again!

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Shahid Mohammed Z.
Drop-In Visits
5.0 out of 5 stars

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!

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Deanna B.
Drop-In Visits
5.0 out of 5 stars

Tierney was super helpful and communicative. She sent detailed updates and photos which I greatly appreciated! Definitely would recommend.

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Nicole C.
Drop-In Visits
5.0 out of 5 stars

Dominick took great care of my cat while I was out of town! She's very responsive and I appreciated all the photos and updates given.

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Lily L.
Drop-In Visits
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How Rover works

  1. 1. Search

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  3. 3. Book & Pay

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Why Choose Rover?

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  • 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.

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    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

Pet Sitting FAQs

Frequently asked questions about Rover

If you’re searching for a Near South Side pet sitter for the first time, visit the pet sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a pet sitter before, learn more about how to do this in the Rover app or on your computer.

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.