House Sitting in Woodlawn, 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
Which dates do you need?
What size are your dogs (lbs)?

Search Results

Calendar Recently Updated
Sitter Profile Image: Lupe M.
Verified Enhanced Background Check
Sitter Profile Image: Lupe M.
Verified Enhanced Background Check
1.

Lupe M.

Ready to help out while you’re away
Gage Park, Chicago, IL, 60632
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
14 reviews
5 repeat clients
from
$90
per night

Lupe was the absolute best sitter we could have asked for! This was the first time we needed to use a sitter and we were anxious about how it would go, she will be our first and hopefully only option moving forward. We received great pictures and updates while we were gone, our pup enjoyed it, and she left our home way better than she found it. Lupe went above and beyond for our dog and it was clear. We couldn’t have been more impressed and grateful. Thank you so much, Lupe!

Calendar Recently Updated
Sitter Profile Image: Katherine B.
Verified Enhanced Background Check
Sitter Profile Image: Katherine B.
Verified Enhanced Background Check
2.

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
14 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.

Sitter Profile Image: Shakira C.
Verified Background Check
Sitter Profile Image: Shakira C.
Verified Background Check
3.

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 is amazing! I feel like she's part of the family. She did an amazing job looking after my Maltipoo, Dash! She sent plenty of pictures and videos throughout the day. I really appreciate the way she made both me and Dash feel comfortable. Before she left, I had already booked her for another sitting for Dash. She's the best!

Calendar Recently Updated
Sitter Profile Image: Masheika S.
Verified Background Check
Sitter Profile Image: Masheika S.
Verified Background Check
4.

Masheika S.

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

Masheika was so professional and cordial! She updated us with pics, messaged about any concerns, and took great care with our pups. We were so comfortable leaving our dogs in her conscientious, capable hands. We'll definitely work with Masheika again!

Calendar Recently Updated
Sitter Profile Image: Shiri B.
Verified Enhanced Background Check
Sitter Profile Image: Shiri B.
Verified Enhanced Background Check
5.

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!

Calendar Recently Updated
Sitter Profile Image: Belicia K.
Verified Background Check
Sitter Profile Image: Belicia K.
Verified Background Check
6.

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

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. When we returned to our apartment it was in the exact same condition we left it, and our two dogs, Juniper and Basil, were calm, healthy, and happy. I will definitely keep Belicia in mind for future dog sitting/walking needs.

Calendar Recently Updated
Sitter Profile Image: Chau T.
Verified Enhanced Background Check
Sitter Profile Image: Chau T.
Verified Enhanced Background Check
7.

Chau T.

Active sitter with huge yard
Englewood, Chicago, IL, 60621
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
1 review
1 repeat client
from
$40
per night

Chau is such the animal whisper. Somehow animals gravitate to her, probably because she understands their boundaries and has a kind soul. I’ve been fortunate to watcher her raise her one year old pup. Her dog is so well behaved and confident, which speaks to the training Chau did with her. Chau is thoughtful and patient. Your fur baby will be in really good hands.

Calendar Recently Updated
Sitter Profile Image: Kelly N.
Verified Enhanced Background Check
Sitter Profile Image: Kelly N.
Verified Enhanced Background Check
8.

Kelly N.

Patient and Compassionate
Kenwood, Chicago, IL, 60615
House Sitting, Doggy Day Care, Dog Walking
2 reviews
1 repeat client
from
$38
per night

Kelly is a reliable person who has the biggest smile when they are with pets. They show deep affection to animals through remembering the little things that animals need to be cared for and have a sense of compassion when the animals are not feeling their best.

Calendar Recently Updated
Sitter Profile Image: Taylor C.
Verified Enhanced Background Check
Sitter Profile Image: Taylor C.
Verified Enhanced Background Check
9.

Taylor C.

Energetic dog lover looking to help
Hyde Park, Chicago, IL, 60615
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
14 reviews
4 repeat clients
from
$30
per night

Taylor was a great dog sitter for GiGi! She sent photos and made sure she was well taken care of. I would highly recommend Taylor for any pet sitting services!

Calendar Recently Updated
Sitter Profile Image: Makeda I.
Verified Enhanced Background Check
Sitter Profile Image: Makeda I.
Verified Enhanced Background Check
10.

Makeda I.

I treat every pet like my own 💕
Chicago, IL, 60619
House Sitting
5.0
3 reviews
from
$51
per night

Makeda was very accommodating when I requested an orientation visit a week or so before the scheduled dogsitting, and impressed me not only by the details she had requested about my dog in advance but also with her recall of what I had told her. She sent several photos of my dog to me while I was away, and apart from a scattering of treats she left for my pet, she otherwise left no trace--very clean and respectful.

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Mikayla A.
Verified Enhanced Background Check
Sitter Profile Image: Mikayla A.
Verified Enhanced Background Check
11.

Mikayla A.

Your furry friend new Buddy!
Chicago, IL, 60619
House Sitting, Drop-In Visits, Dog Walking
10 years of experience
from
$30
per night

About: Ive taken care of animals since i was 13 yrs old. I have rescued many animals & found them great homes. I love all animals. I am currently a part time fitness trainer. So i am available for you & your furry friends after 1pm. Im always available for you & your furry friends! I have a tall fence. I have one Dog & three cats to keep your furry friends active & a great spirit to feed their souls.

Sitter Profile Image: Susan C.
Verified Background Check
Sitter Profile Image: Susan C.
Verified Background Check
12.

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
131 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!

Calendar Recently Updated
Sitter Profile Image: Aolani "Catrina" C.
Verified Enhanced Background Check
Sitter Profile Image: Aolani "Catrina" C.
Verified Enhanced Background Check
13.

Aolani "Catrina" C.

Unmatched Care for Your Pets
Hyde Park, Chicago, IL, 60637
House Sitting, Drop-In Visits, Dog Walking
5.0
7 reviews
1 repeat client
from
$26
per night

Catrina is a wonderful catsitter. Very attentive and caring and able to take care of a special needs kitty like mine. She's also communicative and sends me great pictures. Highly recommended!

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Mikayla V.
Verified Background Check
Sitter Profile Image: Mikayla V.
Verified Background Check
14.

Mikayla V.

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

So fortunate to have found someone who loved hanging with my boy. She was wonderful. My trip was long and she entertained my high energy pup, as well as taking care of him. Great communication and my pup looks very happy. Thanks again!

Calendar Recently Updated
Sitter Profile Image: Maddison C.
Verified Enhanced Background Check
Sitter Profile Image: Maddison C.
Verified Enhanced Background Check
15.

Maddison C.

I love dogs
Chicago, IL, 60649
House Sitting, Drop-In Visits, Dog Walking
1 review
from
$30
per night

Maddison is a amazing and absolutely incredible dog and cat sitter she loves dogs and cat interact with a cats she is very energetic and very caring about animals

Calendar Recently Updated
Sitter Profile Image: John M.
Verified Enhanced Background Check
Sitter Profile Image: John M.
Verified Enhanced Background Check
16.

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.

Calendar Recently Updated
Sitter Profile Image: Emma & Emily F.
Verified Enhanced Background Check
Sitter Profile Image: Emma & Emily F.
Verified Enhanced Background Check
17.

Emma & Emily F.

We love making new furry friends!
Chicago, IL, 60615
House Sitting, Drop-In Visits, Dog Walking
5.0
7 reviews
1 repeat client
from
$65
per night

Hello , I like to tell you about Emma F. Last year my husband and I had to go away for almost 3 month, Emma stayed with our 3 pets (Jake, Luna and Misha). She did a fabulous job at taking care of them, walk them everyday and of course spoiled them. She made sure to update us often as to how our babies were doing. We highly recommend her, I assure you that your pets will be loved and taken very good care with Emma. Marcella and Don

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Kristen W.
Verified Enhanced Background Check
Sitter Profile Image: Kristen W.
Verified Enhanced Background Check
18.

Kristen W.

Fury Friendly Dog Walker
Woodlawn, Chicago, IL, 60637
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
4 reviews
1 repeat client
from
$31
per night

Kristen is great with my two doggies. When she comes to walk them, they get soo excited. She always greets them with hugs and kisses! I always ask her to give them a good jog and they come home tired and panting!! She keeps track of their bodily functions and gives me a full report of how they sniffed, played and reacted towards others. She is the best Doggie Care Giver, EVER!!

Calendar Recently Updated
Sitter Profile Image: Jameson A.
Verified Enhanced Background Check
Sitter Profile Image: Jameson A.
Verified Enhanced Background Check
19.

Jameson A.

Rover 101
A Dog's Life is the Best Life
Hyde Park, Chicago, IL, 60615
House Sitting, Drop-In Visits, Dog Walking
15 years of experience
from
$50
per night

About: I have loved dogs and animals my entire life. My family calls me the dog whisperer. I have many dogs in my family and have pet sat for multiple different breeds, and species in various environments. I am cognizant of different dietary restrictions and medication needs. I have looked after pets for nearly 20 years and treat every animal companion as if they were my own. I currently have an 11-year-old shih tzu, named Scout. He is a rescue and although he is getting up in age, he still acts like a puppy and loves to give kisses. I have lived on the southside for a few years and take my dogs to multiple different parks. You can be confident that when your dog/companion is with me, they are happy, safe, and filled with treats. I wake up at 6 am to start my day and take my dog out. I work from home every day and only need Wifi. I can travel anywhere in the city. I generally take 3-4 walks per day (early morning, midday, afternoon, and late evening). In my home or anyone else’s I treat a pet as my own. I follow all notes and schedules to make sure the animals have a regular and spectacular day. I treat other people’s homes as if they were my grandmother’s, meaning I make sure everything is cleaner than when I arrived.

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Hannah B.
Verified Enhanced Background Check
Sitter Profile Image: Hannah B.
Verified Enhanced Background Check
20.

Hannah B.

Your pups paws are in good hands!
Hyde Park, Chicago, IL, 60615
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
2 reviews
1 repeat client
from
$55
per night

About: Animals are my thing, from the barn to domesticated haha! Book with me you will not regret it 😊 😊 😊 😊 😊 😊 😊 I am able to provide care throughout the days.. my schedule is pretty flexible enough to be able to do this.. . . . . I have done many walks aside from sittings and boardings. I follow instructions to the T to ensure your animal baby’s safety as well as the privacy of your home

Search Map


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.

House Sitting