House Sitting in Woodlawn, Chicago

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

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Maeve P.
1.
Flexible schedule, big fenced yard!Hyde Park, Chicago, IL, 60637
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Maeve did a great job at looking after our two active pooches while we were away for 10 days. She gave regular updates and the house was nice and tidy on our re… (more)

from
$50
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 was great! With manolo she is sweet and patient and loves to cuddle him I think she even spoiled him a little bit with all the cuddles :-) I appreciate… (more)

from
$45
per night
Calendar Recently Updated
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 watched my dog for years and he was always thrilled to stay with her. We always joked that if reincarnation was possible, we wanted to come back as Sus… (more)

from
$45
per night
Brittany K.
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
Nataya J.
5.
Loving care when your not there!!West Englewood, Chicago, IL, 60636
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Nataya did such a great job with dixy my cat. She really feels comfortable with her so I'll be booking Nataya again I when I leave town. (more)

from
$50
per night
Confirmed availability: Memorial day
6.
Enjoying our time step by step!Englewood, Chicago, IL, 60621
House Sitting, Drop-In Visits, Dog Walking

About: I grew up surrounded by animals, therefore I am conscious of how to care for dogs in any situation and in any type of weather and/or environment. Whe… (more)

from
$35
per night
Confirmed availability: Memorial day
I’ll run with your dog. Home FTSouth Shore, Chicago, IL, 60637
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

About: I love caring for pets so I figure what better way to express that than by putting my skills to use through this app. I’m here to make your day less … (more)

from
$60
per night
Confirmed availability: Memorial day
Dog/Cat Care ChicagoGrand Crossing, CHICAGO, IL, 60621
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

About: A true mommy dog lover.I have 2 small Maltese Poodles. Going away for the weekend or Holidays. Allow me to take care of your baby like my own. I live… (more)

from
$40
per night
Calendar Recently Updated
Animal lover 🥰West Englewood, Chicago, IL, 60636
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

About: My name is Christina, I’m a 20 year old woman who’s looking to advance my career with animals. I’ve always dreamed of taking care of them and working… (more)

from
$30
per night
Confirmed availability: Memorial day
10.
🐶+ 🏃🏽‍♂️=😇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
11.
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
12.
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
Confirmed availability: Memorial day
13.
Trustworthy & always punctual.Woodlawn, Chicago, IL, 60637
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

I’ve known Treonna for 6 plus years and for as long as I’ve known her she has always been in love with animals. I’ve watched her take care of dogs who were in a… (more)

from
$30
per night
Student, Library Clerk, & Pet LoverWashington Park, Chicago, IL, 60637
House Sitting, Drop-In Visits, Dog Walking

I've known K for a few years, and she is one of my dog's favorite people! When Fleetwood (Pitbull Mastiff, 2 years old at the time) first met her, he was so hap… (more)

from
$30
per night
Pets need loving care alwaysKenwood, Chicago, IL, 60615
House Sitting, Drop-In Visits, Dog Walking

Christina is one of the most passionate animal lovers that I know. She has not only watched my boys but my dogs as well. With a large Lab and a small Bichon… (more)

from
$25
per night
16.
Peaches The Pet LoverGrand Crossing, Chicago, IL, 60619
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

About: I Have Two Beautiful Babies Mocha + Midnight Both Pit Breeds But Lovely Individuals They Are Great With Other Pets + People We Have A Park Two Bl… (more)

from
$35
per night
17.
Yoga Sitter / Loving+Gentle+SereneSouth Shore, Chicago, IL, 60649
House Sitting, Drop-In Visits, Dog Walking

About: What do you do when you need a gentle + loving sitter, who's caring, a great communicator and loves to do animal yoga then snuggle?  You call me!  Hi… (more)

from
$50
per night
18.
I go above & beyond for pets.Hyde Park, Chicago, IL, 60615
House Sitting, Drop-In Visits, Dog Walking

About: I’m a animal and people person. I graduated from community college with an Associates in theatre arts. I’m available Tuesday’s, fridays and weekends.… (more)

from
$32
per night
19.
Fur Baby Aficionado!Grand Crossing, Chicago, IL, 60619
House Sitting, Drop-In Visits, Dog Walking

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 s… (more)

from
$35
per night
20.
Sam 
Verified Background Check
Experienced Hyde Park Pet-Sitter!Hyde Park, Chicago, IL, 60615
House Sitting, Drop-In Visits, Dog Walking

Sam is great with all animals! She's an experienced pet owner, dog walker, and dog-sitter that I would trust with my own dog any day. (more)

from
$25
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.