House Sitting in Oakland, Chicago

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

1. Emily Verified Background Check

Experience with multiple sized dogs

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Emily is great! Very professional and communicative. A++++ will definitely have her dog sit Niall again ! (more)"

Active and Accepting Requests
2. Michael Verified Enhanced Background Check

I treat your pet like it’s mine.

Near South Side, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Mike was amazing. I am hoping my dogs were well behaved enough he'll want to stay again, ha! He sent updates and pictures throughout the stay. He checked in ... (more)"

3. Nikki Verified Enhanced Background Check

Pet LOVER; making your day easier!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

"Nikki was super nice and friendly. I think she really bonded with our fur baby and he looks super happy and excited to see her when she comes visit. Looking ... (more)"

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4. Annie Verified Enhanced Background CheckRover 101

Your 1st kitty/doggy visit FREE ✔

Near South Side, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

"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 pictur... (more)"

Active and Accepting Requests (incl. from Essential Workers)
5. Gabriel Verified Background CheckRover 101

Will be cared for like family

Hyde Park, Chicago, IL, 60637

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Gabriel took great care of our dog and was a wonderful house sitter! He sent lots of photos from the walks. I would absolutely work with him again. (more)"

6. Tenley Verified Background CheckRover 101

Experienced Dog Owner & Care Giver

Douglas, chicago, IL, 60616

House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Tenley was an excellent sitter! Vincent was very well cared for and our house was left perfectly cleaned and tidy! We will definitely book again with Tenley. (more)"

7. Shaley & Melissa Verified Background Check

Friendly petcare by med student duo

Hyde Park, Chicago, IL, 60615

Dog Boarding, House Sitting, Doggy Day Care, Dog Walking

"Loved seeing all the pics and videos!! Thanks again for taking care of my lil guy! ? (more)"

8. Yue Verified Enhanced Background CheckRover 101

Loving and active sitter/walker!

Lower West Side, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Yue exceeded our expectations while dog sitting for us during last minute travel. She is very professional and an excellent communicator. Yue is a natural ... (more)"

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9. Brianna Verified Background Check

Lover of All Things Furry!

Grand Boulevard, Chicago, IL, 60653

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

"Our dog was very well taken care of under Brianna’s watch! She is very responsible and polite! We appreciated that she sent pictures while we were away! (more)"

10. Naomi Verified Enhanced Background CheckRover 101

Loving & responsible pet caretaker!

Bridgeport, Chicago, IL, 60616

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

"I would highly recommend Naomi as a dog sitter. She is reliable, trustworthy, and goes above and beyond with her care. My animals have always absolutely love... (more)"

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11. Jasmine Verified Enhanced Background Check

Plenty of long walks and treats!

Bridgeport, Chicago, IL, 60609

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Jasmine was fabulous! She sent photos, was highly communicative, came and met our pup first to be sure she was comfortable. This was our first experience wit... (more)"

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12. christine Verified Background Check

Walk and Bark!

Douglas, Chicago, IL, 60616

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care

"She is an amazing dog sitter. She sat one of my friend dog and they always looking forward to have her as a sitter. She has a lot to bring and her patience a... (more)"

13. Ceciley Verified Background Check

Your pet sitting solution

Kenwood, Chicago, IL, 60615

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Ceciley is the perfect sitter. She’s communicative, sharp, friendly, and dependable. We are very grateful to have had her watch our puppy. She cared for Tuna... (more)"

14. Jaureese Verified Background Check

Giving dogs the love they deserve

Kenwood, Chicago, IL, 60653

Dog Boarding, House Sitting

"Reese is the best! When he first met Jordy you could really tell her cared for animals. He had terrific communication throughout his stay. Everything was ext... (more)"

15. Ariadne Verified Background Check

The best care for your best friend

Hyde Park, Chicago, IL, 60615

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"My dog Sammie and I absolutely love Ariadne! She is always kind and caring, very energetic, and always reliable. Nothing but positive experiences every time ... (more)"

Active and Accepting Requests (incl. from Essential Workers)
16. Masheika Verified Background CheckRover 101

Crazy cat lady who loves dogs!

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

"During a recent vacation I asked Masheika to watch my Keshond/Corgi mix Rocky for 5 days and she did an excellent job. She followed all the walking and feedi... (more)"

17. Qiyamah Verified Background Check

Purr-fect Pet Sitter

Oakland, Chicago, IL, 60653

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

About: Hello! I am a College student pursuing a degree in Entertainment Law. I love to babysit and recently decided to extend my services to our four legg... (more)

18. Justice Verified Enhanced Background Check

Trust me, I got you :)

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

About: Since before I was born, there had always been both small and large dogs in the house and family. From Rottweilers, to Maltese, to German Shepards,... (more)

19. Nicole Verified Background Check

Queen of Shibas

Kenwood, Chicago, IL, 60615

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Nicole is devoted to animals, no matter where they come from or who they are. A loving pet owner since childhood, she is always looking for opportunities to ... (more)"

20. Tynetta Verified Background Check

Young, pet lover student in college

Oakland, Chicago, IL, 60653

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

About: I am a student at UIC studying Integrated Health Science and minoring in Chemistry! I have a passion for medicine, cats, dogs and turtles! When I’m... (more)


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.