House Sitting in Kenwood, Chicago

Find a loving dog sitter to watch your dog overnight in your home.

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
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Sitter Profile Image: Jasmine P.
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Sitter Profile Image: Jasmine P.
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1.

Jasmine P.

Rover 101
Beloved dog whisperer, is me!
Chicago, IL, 60604
House Sitting, Drop-In Visits, Dog Walking
5.0
39 reviews
16 repeat clients
from
$75
per night

Jasmine was amazing yet again with my dobie, Storm. I had some last minute emergency changes to my trip and her flexibility and understanding really put me at ease during a stressful time, I'm so grateful for her support! Super communicative, Jasmine took great care of my girl and my place too. Also, Storm is reactive to other dogs and I trust Jasmine to know how to deal with that. Highly recommend.

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Sitter Profile Image: Saniah I.
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Sitter Profile Image: Saniah I.
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2.

Saniah I.

Saniah: Your pets, my love!
Chicago, IL, 60605
House Sitting, Drop-In Visits, Dog Walking
5.0
5 reviews
2 repeat clients
from
$45
per night

Saniah is great! She was on time and clearly showed that she cares for animals, asking about our dog’s favorite toys and treats. I felt entirely comfortable leaving our dog with her in our home and we will be using her again!

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Sitter Profile Image: Crystal R.
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Sitter Profile Image: Crystal R.
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3.

Crystal R.

My home is where your pet is.
Chicago, IL, 60653
House Sitting, Drop-In Visits, Dog Walking
5.0
50 reviews
27 repeat clients
from
$65
per night

Crystal did a great job with our Monty. She was even ready to extend when our flights were cancelled and we were struggling to get back in time. Lots of check-ins and photos - all very reassuring!

Sitter Profile Image: Shakira C.
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Sitter Profile Image: Shakira C.
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4.

Shakira C.

RoverGO
Rover 101
Your Pup is My Pup
South Shore, Chicago, IL, 60649
House Sitting, Drop-In Visits, Dog Walking
5.0
35 reviews
7 repeat clients
from
$75
per night

Shakira was the perfect person to watch our pup for the weekend while we were celebrating our wedding! We immediately felt comfortable after the meet and greet and knew that Sophie would be in great hands in her care. They got along great and she sent so many pictures for us to enjoy during the weekend. Shakira was very calm and helpful when I was concerned that Sophie might have gotten into some medication. She reassured me that Sophie was doing well and that there was nothing to worry about! Shakira took great care of our home as well. She has an all around great energy and we just appreciated her so much! We will definitely call Shakira again next time we need a sitter. Thanks again!

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Sitter Profile Image: Katherine B.
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Sitter Profile Image: Katherine B.
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5.

Katherine B.

🐶Who's a good dog? Trick question!
Grand Boulevard, Chicago, IL, 60615
House Sitting, Drop-In Visits, Dog Walking
5.0
47 reviews
13 repeat clients
from
$75
per night

Simply amazing. We recieved many updates, and came home to a happy and healthy dog and apartment in great condition. Would happily recommend have watch our dog again.

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Sitter Profile Image: Jessica K.
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Sitter Profile Image: Jessica K.
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6.

Jessica K.

Caring for Your Pet Like My Own
Near South Side, Chicago, IL, 60616
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
2 reviews
from
$45
per night

Highly recommend! Jessica is phenomenal. An overachiever to say the least. She makes my pets feel so, so comfortable like they're her own. It's obvious she cares for my furry children and, also, makes me feel so comfortable. I believe she is a teacher during the day, which may explain her thorough and caring nature when coming over to take care of my guys.

Sitter Profile Image: Shiri B.
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Sitter Profile Image: Shiri B.
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7.

Shiri B.

Kind and practical pet lover
Chicago, IL, 60621
House Sitting, Drop-In Visits, Dog Walking
5.0
7 reviews
from
$50
per night

Shiri was awesome to accept a relatively last minute booking at a good rate, and was communicative and professional throughout her stay. I returned to my home exactly how I had left it for her which I appreciated as well. She was understanding and kind when problems arose which meant a lot for me given my dog is of old age and caring for him can be quite involved. Thanks Shiri!

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Sitter Profile Image: Belicia K.
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Sitter Profile Image: Belicia K.
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8.

Belicia K.

Cats and dogs are my sunshine!
Englewood, Chicago, IL, 60621
House Sitting, Drop-In Visits, Dog Walking
5.0
12 reviews
6 repeat clients
from
$50
per night

My cat sitter cancelled on me at the last minute. But as it turns out I was meant to find Belicia. She took excellent care of my girl Zuri. Belicia was communicative, kind, and followed all instructions. She sent me messages and photos to absolve any worry and it didn't take long for my anti-social kitty to take to her. Having her care for Zuri was such a peace of mind. When I came back home, I realize that everything worked out as it should have. This is the beginning, as I will be scheduling with Belicia again.

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Sitter Profile Image: Mags A.
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Sitter Profile Image: Mags A.
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9.

Mags A.

Lover of all animals and long walks
Douglas, Chicago, IL, 60616
House Sitting, Drop-In Visits, Dog Walking
5.0
37 reviews
15 repeat clients
from
$72
per night

Mags stayed for two night at my place to watch over my dog, cat, and lizard, and did an exceptional job! The house looked just how I left it and my fur babies were loved and well cared for! Mags was readily available for any communication needed and responded promptly, including pictures of the animals! We are thankful for Mags, and will definitely be using her in the future!

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Sitter Profile Image: John M.
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Sitter Profile Image: John M.
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10.

John M.

UChicago student; animal lover
Hyde Park, Chicago, IL, 60637
House Sitting, Drop-In Visits, Dog Walking
2 reviews
from
$50
per night

John is a responsible student and pet enthusiast who would make a wonderful caretaker for any furry friend. John has experience taking care of his own three dogs back home, including one who is geriatric and disabled. He never fails to pet a pup on the street, and is a favorite among his friends cats, whom he regularly cares for. John is very reliable, and will take outstanding care of any pet.

Sitter Profile Image: Raeanna H.
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Sitter Profile Image: Raeanna H.
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11.

Raeanna H.

Pawsitively Caring Pet Sitter
Chicago, IL, 60615
House Sitting, Drop-In Visits, Dog Walking
3 reviews
from
$60
per night

Raeanna was great with Buddy & Jett. I would highly recommend her for staying with your pets.

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Sitter Profile Image: Emily L.
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Sitter Profile Image: Emily L.
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12.

Emily L.

Love all pets 🫶
Hyde Park, Chicago, IL, 60637
House Sitting, Drop-In Visits
5.0
2 reviews
from
$35
per night

About: I’ve had a few pets of my own and I am very detail oriented, if your pets ever need me to go an extra mile I will! I am currently a college students at the University of Chicago. I have free time after classes, on weekends and some holidays. I would love to work as a pet sitter or walker! I won’t be home sitting because I live in a dorm right now, but I can home sit at your homes! I care very much for animals and will give them my undivided attention.

Sitter Profile Image: Masheika S.
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Sitter Profile Image: Masheika S.
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13.

Masheika S.

Rover 101
Full time pet sitter :)
Chicago, IL, 60653
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
56 reviews
20 repeat clients
from
$100
per night

Masheika is awesome and I am pretty sure my dog would leave me for her. During her time sitting, she stayed in regular contact with updates and photos. I felt completely confident and comfortable with her and will definitely, definitely re-book if we ever get to go out of town again. During the meet and greet, I could immediately tell Masheika the kind of special spirit that animals gravitate towards. My dog was immediately stuck to her side and I felt completely assured that they would be great while I was gone. He's a very sensitive dog and it was so comforting knowing that he was being taken care of by a caring person instead of being kept in a kennel. Highly recommend!!

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Sitter Profile Image: Michael P.
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Sitter Profile Image: Michael P.
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14.

Michael P.

Diabetes Puuurficient Cat Dad
Chicago, IL, 60653
House Sitting, Drop-In Visits, Dog Walking
6 reviews
from
$55
per night

I don’t usually review anything but on this case i have to to do it for Michael He’s the right person for this job for sure👍

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Mikayla V.
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Sitter Profile Image: Mikayla V.
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15.

Mikayla V.

Fur Baby Aficionado!
Chicago, IL, 60637
House Sitting, Drop-In Visits
5.0
23 reviews
9 repeat clients
from
$55
per night

Mikayla was awesome! My animals were so happy and she was in communication at all times. I even came home to a cute welcome message. If you are looking for someone to shower your pups with love, Mikayla is the perfect sitter. Definitely put Mikayla on your short list!

Sitter Profile Image: Susan C.
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Sitter Profile Image: Susan C.
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16.

Susan C.

You're Dog is My Dog!
Hyde Park, Chicago, IL, 60615
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
130 reviews
56 repeat clients
from
$60
per night

I can’t say enough about Susan and the way she cares for my Mocha! I never have a moment’s worry while Mocha is in her care. She updates me frequently with texts and photos and it’s evident how much she cares for her. Until the next time…our 3 week trip to South Africa…..check “dog care” off the to do list… There’s no one I’d trust more than Susan!

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Sitter Profile Image: Ashley B.
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Sitter Profile Image: Ashley B.
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17.

Ashley B.

Open house for Pets
Hyde Park, Chicago, IL, 60615
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
53 reviews
32 repeat clients
from
$80
per night

Ashley is a dependable person who value her work. She's also a very friendly and pet friendly person . Anytime she sees a dog her face glow with excitement and joy. Before walking up to any dog I have seen her stop introduce herself to the owner and ask for permission to pet the dog. Once given permission she talks and play with the dogs becomes one with the dog. I have seen many dogs happy and pleased with her company. A couple of months back Ashley dog sit form. I have Chihuahua name Barbie whose 2 year of age. Ashley kept Barbie for me for a whole week, kept her on her walking eating and play schedule. When it was time for me to take Barbie home she was full of joy and groomed. Barbie enjoyed herself with Ashley so much which made me say play dates for them to continue the bond they made with each other. I was very pleased with her help!

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Sitter Profile Image: Viola R.
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Sitter Profile Image: Viola R.
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18.

Viola R.

A dogs best friend
Grand Boulevard, Chicago, IL, 60615
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0
7 reviews
3 repeat clients
from
$65
per night

Viola is an awesome pet care provider. My family has benefited greatly as Viola as our home away from home for our German Shepherd. Viola is always prompt and courteous. My dogs live her gentleness.

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Sitter Profile Image: Asia M.
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Sitter Profile Image: Asia M.
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19.

Asia M.

They’re not justpets,they’re family
Chicago, IL, 60615
Boarding, House Sitting, Drop-In Visits, Doggy Day Care
5.0
9 reviews
5 repeat clients
from
$50
per night

Asia was amazing watching my pets while I was on vacation. Without even asking, she texted me daily with photos and giving me updates on what they were doing. My home was as clean as I left it and you wouldn't have even known she was here. She was respectful, neat and tidy. Couldn't have been a better experience. I will definitely use Asia and this service in the future.

Sitter Profile Image: Andreana W.
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Sitter Profile Image: Andreana W.
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20.

Andreana W.

Pets are live-in best friends🐶💜
Kenwood, Chicago, IL, 60653
House Sitting, Drop-In Visits, Dog Walking
5.0
1 review
2 repeat clients
from
$40
per night

About: I have always had pets as a child and the responsibility to care after them like I would my siblings. But as I have gotten older I have been provided the luxury of owning pets I can call my own and raise how I see fit (which is code for spoil). I wont put some long drawn out advertisement of why you should pick me to care for your fur baby, but just understand that everyone tells me how I treat TuTu more like a child than I do the human one 🙂 Thats how much i love pets, and how important it is to make them feel part of the family! And if you decide to trust me with your pet, just know they will always be treated the same while in my care💜 I work a full-time job in IT, but very flexible and mostly remote. So i am pretty open and available when needed. Also very respectful of your time, so i will always be open and communicate any conflicts that may arise. I currently have a 3 year old Shitzhu that is full of energy and love to be around other dogs. Extremely (overly) friendly and very welcoming lol. I also have a cat that is pretty antisocial, so in the instance you would prefer my home, i will put her in her up in her own room. I stay in a duplex, so plenty of room to be comfortable. Also, we go on multiple walks a day so plenty of exercise will be provided along with belly rubs.

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The next time you head out of town and need someone to take care of your pet - and your home - turn to Rover for your house sitting needs. It's easy to find a loving pet sitter on Rover who'll give your pet one-on-one attention while you're away, and take care of your home. Search from hundreds of trusted house sitters near you, read sitter profiles, and reach out to sitters who seem like a good fit for you and your pet. We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. Then, when you're ready, book and pay for your house and pet sitter all through Rover - it's easy, safe, and cashless. You'll have the peace of mind knowing that your sitter has free premium insurance, a team of safety experts available 24/7, and will send you cute photo updates throughout the stay. Rover is the easiest way to find trustworthy house sitters for your pets--and avoid the kennel.

Want to learn more? Check out reviews from pet owners who have used Rover.

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