House Sitting in Oakland, Chicago

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

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.

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

Pablo was a great sitter for my little pup, Harlow. She was recently put on some meds and he gave her those with no problem; greatly relieving my stress about l… (more)

from
$59
per night
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Nerina M.
2.
Animal shelter profess./pet lover!Gage Park, Chicago, IL, 60632
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Nerina was amazing with our dog Wanda! She was very responsive, gave us several updates while we were gone, and was great company for our dog while we were away… (more)

from
$60
per night
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Vladimir C.
Fulltime attention 💛💙 loads of 📸Near North Side, Chicago, IL, 60611
Dog Boarding, House Sitting

Vladimir was an excellent sitter. He sent a photo and updates of Scruffy everyday. They even took a portrait photo! I definitely recommend him. (more)

from
$54
per night
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Aubry P.
4.
Pet Lover with 10+ Years ExperienceLoop, Chicago, IL, 60605
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Aubry was great with our anxious senior dog! She took great care of her, giving her lots of walks and snuggles. She also left our house clean and ready for us t… (more)

from
$60
per night
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Susan C.
5.
You're Dog is My Dog!Hyde Park, Chicago, IL, 60615
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Susan was terrific with our two dogs. When we met her prior to her stay, we knew they were in good hands. She sends lots of updates and treats your dogs like th… (more)

from
$60
per night
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6.
Lifelong Pet Lover and OwnerLoop, Chicago, IL, 60601
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Kailee is incredible!! She house sat my two Golden Retrievers while I was out of town, and she did the best job! She sent updates and pictures every day. She as… (more)

from
$50
per night
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7.
Offering unlimited FREE belly rubs!Near North Side, Chicago, IL, 60654
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Brett is fantastic - responsible, responsive and very caring. He looked after our sweet, but naughty 9 month old puppy over thanksgiving and we couldn’t be more… (more)

from
$90
per night
A friend that caresLoop, Chicago, IL, 60660
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Jonathan took such good care of our dog while we were away! They went on long walks and our dog looked super happy in every picture he sent. Jonathan sent descr… (more)

from
$60
per night
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9.
Dog owner and animal loverLoop, Hamilton, IL, 60601
House Sitting, Drop-In Visits, Dog Walking

Maya is a fantastic cat sitter. Penelope is an anxious cat, but when Maya stays over, she is relaxed and a very happy cat when I come home. When I travel, I k… (more)

from
$50
per night
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Full time and insured pet sitter :)Grand Boulevard, Chicago, IL, 60653
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
$60
per night
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11.
Experience with multiple sized dogsBridgeport, Chicago, IL, 60616
House Sitting, Drop-In Visits, Dog Walking

It was a relief to know that my dog was well taken care of while we were in the hospital having a baby. I appreciated the daily check-ins and communication. (more)

from
$40
per night
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12.
Amy 
Verified Enhanced Background Check
Enthusiastic Dog AdorerLoop, Chicago, IL, 60604
Dog Boarding, House Sitting, Doggy Day Care

Amy B has a natural connection with dogs, as they have with her. Caring and generous with her time, she will treat your dog as if it were her own. She has taken… (more)

from
$50
per night
Confirmed availability: Memorial Day
13.
Love and attention for all animalsBridgeport, Chicago, IL, 60608
House Sitting, Drop-In Visits, Dog Walking

Sujae has taken care of my furry crew a couple of times now and it really helps to know they are in great hands while I have to be away. (more)

from
$40
per night
Confirmed availability: Memorial Day
14.
Your 1st kitty/doggy visit FREE ✔Armour Square, Chicago, IL, 60616
House Sitting, Drop-In Visits

Annie watched our French Bulldog, Fiona, for 7 days. It was also a holiday weekend which is a big deal. She did a great job with Fiona! She would send pictures … (more)

from
$70
per night
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Experienced vet assistant & fosterLower West Side, Chicago, IL, 60608
House Sitting, Drop-In Visits, Dog Walking

Stephanie was so great! She communicated with us the whole time and sent picture updates. She took very good care of Radley - we will definitely be using her ag… (more)

from
$28
per night
Confirmed availability: Memorial Day
16.
Hardworker and lover of animals!Loop, Chicago, IL, 60605
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Raven is a very sweet and out-going girl! She has a very deep love for animals and has always taken very good care of them. (more)

from
$40
per night
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17.
Reliable routine Queen for your petBridgeport, Chicago, IL, 60608
House Sitting, Drop-In Visits, Dog Walking

As someone who has known Erin since she was young, I've always known her as someone who loves animals. When getting into her first apartment – she immediately t… (more)

from
$30
per night
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18.
No ruff times, making a pet friend.Near South Side, Chicago, IL, 60605
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Angel has both walked and watched my dogs when I am out of town. She is communicative, professional and does so well with both of my pups. She is my go to anyti… (more)

from
$30
per night
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19.
Yoga Sitter / Loving+Gentle+SereneWoodlawn, Chicago, IL, 60637
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking
10 years of experience

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
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Happy pup happy life!Douglas, Chicago, IL, 60616
House Sitting

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
$35
per night

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.