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
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What size are your dogs (lbs)?

Search Results

Sitter Profile Image: Emily N.
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Sitter Profile Image: Emily N.
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1. Emily N.

Experience with multiple sized dogs
Bridgeport, Chicago, IL, 60616
4.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
111 reviews
35 repeat clients
from
$55
per night

I was very nervous as a first time Rover user and so happy I found Emily! She asked detailed questions about my dogs care and habits during our initial meet and greet which put me at ease, sent photo updates during her stay where he seemed very happy / comfortable with her and came home to a clean place. Would definitely book again!

Sitter Profile Image: Belicia K.
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Sitter Profile Image: Belicia K.
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2. Belicia K.

Cats and dogs are my sunshine!
Englewood, Chicago, IL, 60621
2.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
13 reviews
7 repeat clients
from
$50
per night

Belicia is wonderful! I felt so comfortable leaving my girl with her. She’s so communicative and thoughtful, I can’t wait to work with her again!

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Sitter Profile Image: Elizabeth D.
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Sitter Profile Image: Elizabeth D.
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3. Elizabeth D.

Does your pet need a new friend?
Douglas, Chicago, IL, 60609
3.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
24 reviews
5 repeat clients
from
$33
per night

Elizabeth was so great! We were able to meet before the house sitting and went over the specifics of my dog. She gave me daily updates and let me know he was doing well which I really appreciated!! I would definitely book again ?

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Sitter Profile Image: Jasmine P.
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Sitter Profile Image: Jasmine P.
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4. Jasmine P.

Rover 101
Beloved dog & cat whisperer, is me!
Chicago, IL, 60615
2.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
58 reviews
21 repeat clients
from
$75
per night

What an incredible sitter! Jasmine house sat and watched my puppy and cat for 1 week and was so patient with my stubborn, mouthy puppy (who still isn’t house & crate trained). She sent me multiple updates a day and even continued with his training plan + added some of her own tricks to his repertoire - can’t say enough good things about Jasmine and would definitely rebook her as a sitter in the future!! I really appreciated her going above and beyond to help with his training - her experience dealing with large breeds was such a blessing!

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Sitter Profile Image: Sarah S.
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Sitter Profile Image: Sarah S.
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5. Sarah S.

Rover 101
Experienced Animal Care
Bridgeport, Chicago, IL, 60609
4.2 mi. away
House Sitting
5.0 out of 5 stars
57 reviews
12 repeat clients
from
$55
per night

Sarah has watched our dogs twice nice for an extended weekend both times. She arrives promptly, is neat and tidy when in our home and she always treats our dogs well. They enjoy her as their sitter and we highly recommend her!

Sitter Profile Image: Shakira C.
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Sitter Profile Image: Shakira C.
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6. Shakira C.

RoverGO
Rover 101
Your Pup is My Pup
South Shore, Chicago, IL, 60649
1.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
36 reviews
7 repeat clients
from
$75
per night

Shakira entered like a piece to our puzzle. Parenting tiny dogs with some special needs can make it challenging to get away as a couple for a long day so travel as a couple became impossible. Shakira made introduction easy and comforting for us and our dogs. Arriving on time, she prompted all the questions for a thorough dialog, instilled trust quickly, and exuded a confidence that every doggie parent needs to feel relaxed when then leave. We look for opportunities to get away together now that we have our solution - Shakira.

Sitter Profile Image: Katherine B.
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Sitter Profile Image: Katherine B.
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7. Katherine B.

🐶Who's a good dog? Trick question!
Grand Boulevard, Chicago, IL, 60615
2.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
55 reviews
15 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.

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Sitter Profile Image: Jessica S.
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Sitter Profile Image: Jessica S.
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8. Jessica S.

Passionate Pet Care Pro
Chicago, IL, 60649
0.7 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$30
per night

Jessica is simply the best when it comes to pet care! She's like a second mom to our furry family members. Always reliable and caring, Jessica goes out of her way to make sure our pets are happy and healthy. We couldn't ask for a better caregiver! Thanks, Jessica, for all you do!

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Sitter Profile Image: Emma & Emily F.
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Sitter Profile Image: Emma & Emily F.
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9. Emma & Emily F.

We love making new furry friends!
Hyde Park, Chicago, IL, 60615
1.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
17 reviews
3 repeat clients
from
$50
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

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Sitter Profile Image: Taylor C.
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Sitter Profile Image: Taylor C.
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10. Taylor C.

Energetic dog lover looking to help
Hyde Park, Chicago, IL, 60615
1.4 mi. away
Boarding, House Sitting, Doggy Day Care
5.0 out of 5 stars
20 reviews
8 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!

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Sitter Profile Image: Stephanie J.
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Sitter Profile Image: Stephanie J.
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11. Stephanie J.

They are special like we are!
South Shore, Chicago, IL, 60649
1.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
1 review
from
$45
per night

Stephanie was wonderful to Layla. She made Layla feel comfortable right away. I also appreciated how attentive Stephanie was to our changing needs. She was also early to arrive which I was happy about since we had an appointment we needed to get to.

Sitter Profile Image: Shiri B.
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Sitter Profile Image: Shiri B.
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12. Shiri B.

Kind and practical pet lover
Chicago, IL, 60621
2.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
9 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!

Sitter Profile Image: Aolani "Catrina" C.
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Sitter Profile Image: Aolani "Catrina" C.
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13. Aolani "Catrina" C.

Unmatched Care for Your Pets
Hyde Park, Chicago, IL, 60637
0.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
13 reviews
3 repeat clients
from
$28
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!

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Sitter Profile Image: Raeanna H.
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Sitter Profile Image: Raeanna H.
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14. Raeanna H.

Pawsitively Caring Pet Sitter
Chicago, IL, 60615
2.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
4.5 out of 5 stars
5 reviews
from
$60
per night

Raeanna house sat for us during Thanskgiving. She fed the cats and left our house the way we left it. Only giving her 4 stars because she came late (6.5 hours after the booking time) and left earlier than the booking time - she did ask me if she could leave early.

Sitter Profile Image: Mikayla V.
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Sitter Profile Image: Mikayla V.
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15. Mikayla V.

Fur Baby Aficionado!
Chicago, IL, 60637
1.1 mi. away
House Sitting, Drop-In Visits
5.0 out of 5 stars
24 reviews
9 repeat clients
from
$70
per night

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 someone to shower your pups with love, Mikayla is the perfect sitter. Definitely put Mikayla on your short list!

Confirmed availability: Easter Weekend
Sitter Profile Image: Dominique F.
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Sitter Profile Image: Dominique F.
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16. Dominique F.

Caring For Your Pet With Respect❤️
South Shore, Chicago, IL, 60637
0.9 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
58 reviews
34 repeat clients
from
$65
per night

About: Hi I'm Dominique, here to get out and walk Dogs or just be a friendly companion for your pets. I understand deeply the responsibility of careing for and loving our furry friends. What's better than knowing your furry friend is happy and healthy especially after being back from a busy day, or just knowing someone is there to help when your just not feeling good! That someone is me! I couldn't have found a better Gig! All animals deserve the attention they desire! They deserve to live a good life and get fresh air. I'll be there as a helping hand so please be detailed as possible with your pets individual needs and I assure a great visit. I'm a full time worker for rover, I have a 1 bed apartment in Pilsen very dog friendly neighborhood. I am available so contact me 😊 thank you. I have been caring for animals my whole life I have their best interest. Thanks for choosing river I am available full time. Contact me anytime!

Confirmed availability: Easter Weekend
Sitter Profile Image: Emily L.
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Sitter Profile Image: Emily L.
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17. Emily L.

Love all pets 🫶
Hyde Park, Chicago, IL, 60637
0.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
3 reviews
from
$60
per night

About: I’ve had a few pets of my own and I am very detail oriented, if your pets ever need me to go an extra mile I will! I am currently a college students at the University of Chicago. I have free time after classes, on weekends and some holidays. I would love to work as a pet sitter or walker! I won’t be home sitting because I live in a dorm right now, but I can home sit at your homes! I care very much for animals and will give them my undivided attention.

Sitter Profile Image: Jonah S.
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Sitter Profile Image: Jonah S.
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18. Jonah S.

Around HP - flexible schedule
Hyde Park, Chicago, IL, 60615
1.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 reviews
2 repeat clients
from
$60
per night

Jonah dog sat Cinnamon and he did a great job with her! I appreciate the daily updates while I was away and that he kept my place tidy. Thank you, Jonah! I will be calling Jonah again in the future.

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Sitter Profile Image: John M.
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Sitter Profile Image: John M.
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19. John M.

UChicago student; animal lover
Hyde Park, Chicago, IL, 60637
1.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
1 repeat client
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.

Sitter Profile Image: Jessy M.
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Sitter Profile Image: Jessy M.
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20. Jessy M.

Avid runner who loves all pets
Hyde Park, Chicago, IL, 60615
1.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
5 reviews
from
$30
per night

Jessy was a great help to us in watching our old dog while we traveled for several days and we are so grateful for that she stayed at our place to keep our dog company. She is responsible, friendly, a good communicator, and great with dogs. Our dog is a bit high maintenance as she has aged and Jessy handled all of our notes and the dog's idiosyncrasies very well. We would highly recommend her to take care of any pets!

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Rover also offers House Sitting in these neighborhoods:

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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