House Sitting in Woodlawn, 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.

Search Results

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Nerina M.
1.
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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Susan C.
2.
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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Emily N.
3.
Experience with multiple sized dogsBridgeport, Chicago, IL, 60616
House Sitting, Drop-In Visits, Dog Walking

Emily was absolutely fantastic. She watched our dog for five days and stayed in our apartment- she sent us great updates and did a wonderful job sticking to our… (more)

from
$40
per night
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Masheika S.
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
Confirmed availability: Memorial Day
Maria C.
5.
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
$50
per night
Confirmed availability: Memorial Day
6.
Loving care when your not there!!West Englewood, Chicago, IL, 60636
House Sitting, Drop-In Visits, Dog Walking

Nataya is always there in a pinch and Inga is always so excited to see her! She gives me updates often and is really flexible when I need it. Really appreciate … (more)

from
$70
per night
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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
Calendar Recently Updated
8.
Young professional who loves pets!Hyde Park, Chicago, IL, 60615
House Sitting
4 years of experience

About: I have chased down & safely caught two runaway dogs for strangers. Growing up in Chicago, I have house, and pet sat since I was 17, and baby sat sinc… (more)

from
$30
per night
Confirmed availability: Memorial Day
Beloved dog whisperer, is me!South Shore, Chicago, IL, 60649
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

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 e… (more)

from
$55
per night
Confirmed availability: Memorial Day
10.
Cats and dogs are my sunshine!Englewood, Chicago, IL, 60621
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Belicia was an amazing sitter who communicated with us often. She immediately put us at ease by sending us pictures, videos, details regarding every walk, etc. … (more)

from
$40
per night
Confirmed availability: Memorial Day
11.
No job is to big no pup is to smallSouth Chicago, Chicago, IL, 60617
House Sitting, Drop-In Visits, Dog Walking

About: When it comes to walking dogs. It’s a wonderful feeling to just be on a stroll while being accompanied by Mans best friend. Every pet will get much e… (more)

from
$90
per night
Confirmed availability: Memorial Day
12.
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
$55
per night
Confirmed availability: Memorial Day
I’ll treat your babies as I do mineGrand Crossing, Chicago, IL, 60619
House Sitting, Drop-In Visits, Dog Walking
4 years of experience

About: I have always been around animals. Whether it be fish, birds, amphibians, spiders, rabbits, dogs, and cats. I noticed animals have always taken a lik… (more)

from
$30
per night
Confirmed availability: Memorial Day
All Creatures, Great and SmallHyde Park, Chicago, IL, 60615
House Sitting, Drop-In Visits, Dog Walking

If you need someone who is: 1. Dedicated 2. Loyal 3. A great pet sitter/Lover 4. Flexible with scheduling 5. Local Then Lisa is your Best Choice. She has… (more)

from
$100
per night
Calendar Recently Updated
15.
Attentive & Loving Walker HereWoodlawn, Chicago, IL, 60637
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

My relationship with Antonio, has grown into a friendship. He played a major role in helping my extremely shy bulldog, become more outgoing; and interactive wit… (more)

from
$37
per night
16.
Treat your furry Friend like FamilySouth Shore, Chicago, IL, 60649
House Sitting, Drop-In Visits, Dog Walking
5 years of experience

About: HI, my name Alicia and I live on the east side of Chicago. I'm a very out going person that love life and meeting new people. I had many pets through… (more)

from
$30
per night
Confirmed availability: Memorial Day
17.
Hello! Im Britney I ❤️ PetsHyde Park, Chicago, IL, 60615
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

I will definitely leave my pug with Britney again, the attention she gave to my dog was excellent, She treats muñeca with care and love, She took her on walks a… (more)

from
$60
per night
18.
Dee 
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Hyde Park Dog LoverKenwood, Chicago, IL, 60615
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Dee is THE best doggie caretaker I’ve ever encountered! She truly loves dogs and is responsible and fun. My dog has a Fitbark so I can track her steps and I kno… (more)

from
$40
per night
Calendar Recently Updated
19.
Caring and experienced dog loverKenwood, Chicago, IL, 60615
House Sitting, Drop-In Visits, Dog Walking

Sarah is INCREDIBLE with dogs. Some people just vibe real well with all types of dogs no matter the situation, she’s that person. She’s a paramedic so she bring… (more)

from
$50
per night
Confirmed availability: Memorial Day
20.
On the move and ready to help!Washington Park, Chicago, IL, 60637
House Sitting, Drop-In Visits, Dog Walking
4 years of experience

About: Hello! My pet care experience started when I was in college when I was need of some income while going classes. My experience has been amazing becaus… (more)

from
$20
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.