House Sitting in Oakland, Chicago

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

Pablo V.
1.
Fun walksNear West Side, chicago, IL, 60661
House Sitting, Drop-In Visits, Dog Walking

Pablo was amazing. He helped us out when our other sitter had to cancel last minute. He was flexible and did not at all seem bothered by our last minute reques… (more)

from
$52
per night
Calendar Recently Updated
Maeve P.
2.
Flexible schedule, big fenced yard!Hyde Park, Chicago, IL, 60637
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Maeve was house sitting for us for over a month taking care of our cat. She was amazing - took great care of the cat, house, kept in touch. Our cat took to her … (more)

from
$50
per night
Confirmed availability: Memorial day
Susan C.
3.
You're Dog is My Dog!Hyde Park, Chicago, IL, 60615
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Susan would be a fabulous dog sitter! She has had dogs with special/physical needs, so her compassion knows no bounds. She’s extremely responsible, kindhearted,… (more)

from
$45
per night
Confirmed availability: Memorial day
Masheika S.
Vaccinated animal lover. :)Hyde Park, Chicago, IL, 60615
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Masheika is an absolute gem. This is the second time I've hired her, and she continues to be incredible. She remembered everything about my cats, including medi… (more)

from
$45
per night
Edilberto V.
Passionate Pet Care ProviderLoop, Chicago, IL, 60604
House Sitting, Drop-In Visits, Dog Walking

Eddie obviously loves dogs and takes his job very seriously. Responsible and intelligent. Will use him over and over for our treasured four-legged family membe… (more)

from
$50
per night
Happy pup happy life!Douglas, Chicago, IL, 60616
House Sitting, Drop-In Visits, Dog Walking

Brittany took excellent care of our pup and our place. We came home to such a happy dog after a week away, and it was great to receive daily updates with pictur… (more)

from
$30
per night
7.
Loving care when your not there!!West Englewood, Chicago, IL, 60636
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Nataya is so loving and caring. She always puts the needs of others first and is the first person to help. Nataya is great with my dogs Passion and Cloe. They a… (more)

from
$50
per night
Calendar Recently Updated
8.
Amazing Animal CaregiverLoop, Chicago, IL, 60605
House Sitting, Drop-In Visits, Dog Walking

Emma is a very close friend of mine and she is a great pet owner! She has watched my dog and cats before and I’ve always been more than satisfied with her servi… (more)

from
$50
per night
Confirmed availability: Memorial day
9.
Trustworthy, respectful, and fun!Near South Side, Chicago, IL, 60616
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Nikki was an excellent sitter. Sammie was in great hands and had a blast. Came back to a healthy boy and a respectfully cared for home. Would highly recommend! (more)

from
$40
per night
Confirmed availability: Memorial day
10.
Great with Dogs!Lower West Side, Chicago, IL, 60608
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Great stay, our shibas were well taken care of while we were gone with daily updates and pictures. Tylor even stayed a little extra when it turned out we wouldn… (more)

from
$40
per night
Calendar Recently Updated
11.
Animal lover working from homeNear South Side, Chicago, IL, 60605
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Livia is extremely kind, responsible, and caring! She is amazing with my pets and is extremely trustworthy. She loves all animals and has the natural ability to… (more)

from
$40
per night
Calendar Recently Updated
12.
Home Full Time-Big Fenced in SpaceBridgeport, Chicago, IL, 60608
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care

Randi takes great care of Obi, my Berner Mountain Dog, when I'm out of town. He's always happy to see her. I can trust that he's in good care with Randi. I high… (more)

from
$70
per night
Calendar Recently Updated
13.
I love dogs and dogs love me!Near South Side, Chicago, IL, 60605
House Sitting, Drop-In Visits, Dog Walking

Libby was great with our dog, Cleo. She accepted the last minute request quickly and was able to do a meet & greet that same day, which was a huge help! Libby w… (more)

from
$50
per night
Calendar Recently Updated
Care your baby like my ownNear South Side, Chicago, IL, 60605
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Chanakarn was great! Super responsive and left me with no concerns while she was watching my pets. I came back to them happy and content. I’d definitely use he… (more)

from
$50
per night
15.
Dogs are four legged best friendsGrand Boulevard, Chicago, IL, 60615
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Pamela is a wonderful dog owner and caregiver. She is a yorkie mom and loves to interact and spoil her baby. Seeing her interact with other dogs makes me realiz… (more)

from
$75
per night
Confirmed availability: Memorial day
16.
🐶+ 🏃🏽‍♂️=😇Washington Park, Chicago, IL, 60621
House Sitting, Dog Walking

Terrell was and is the only person I tursted other than myself to watch my dog. Whenever I needed him too he kept my dog on his schedule. When I came home from … (more)

from
$30
per night
Calendar Recently Updated
17.
Love spending time with your petKenwood, Chicago, IL, 60653
House Sitting, Drop-In Visits, Dog Walking

Daniel has been perfect with pets his entire life. As his mother, I can tell you there’s never been a cat that I’ve owned that’s not warmed up to him. He is a … (more)

from
$30
per night
Our sweet dog loves friends!Near South Side, Chicago, IL, 60616
House Sitting, Drop-In Visits, Dog Walking

Very professional! I received pictures throughout my stay. My pup was spoiled, happy and well taken care of. It helped put my mind at ease while we were away. I… (more)

from
$50
per night
Calendar Recently Updated
19.
Plenty of long walks and treats!Bridgeport, Chicago, IL, 60609
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Jasmine was fabulous! She sent photos, was highly communicative, came and met our pup first to be sure she was comfortable. This was our first experience with R… (more)

from
$30
per night
Confirmed availability: Memorial day
20.
Dogs are a humans bestfriend.Hyde Park, Chicago, IL, 60615
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Roxy is a very responsible dog walking always on time very dependable she took very good care of my dog when she toom my dog on walks my dog loves her walks wit… (more)

from
$35
per night

Rover also offers House Sitting in:


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.