House Sitting in Oakland, Chicago

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

1. TIANJIAO

Ariel's Dog Haven

Kenwood, CHICAGO, IL, 60615

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

5 repeat clients

"I cannot say enough great things!! She watched our 9 month old furchild and I felt completely comfortable and at ease knowing she was in Tianjiao’s hands! Sh... (more)"

Confirmed Memorial day Availability
2. Nina

Student & home often, love to run!

Hyde Park, Chicago, IL, 60637

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

"Nina has cared for our beloved Dobby multiple times. He is always so excited when we drop him off! I appreciate that Nina sends me lots of photos of the fun ... (more)"

3. Payal

West Town Pet Sitter

McKinley Park, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

23 repeat clients

"Payal was amazing! It is hard to leave your pet, but she made us feel completely at ease when we were on vacation. Would most definitely recommend!! :) (more)"

Confirmed Memorial day Availability
4. Robert

All furry friends welcome!

Loop, Chicago, IL, 60601

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

43 repeat clients

"Robert was absolutely fantastic in taking care of our pet when we were away. He was very honest and provided regular updates. I would definitely use him in t... (more)"

5. Edilberto

Passionate Pet Care Provider

Loop, Chicago, IL, 60604

House Sitting, Drop-In Visits, Dog Walking

19 repeat clients

"Eddie house sat my dog Bentley for a night. My husband and I have never used a sitter before so we were anxious but Eddie had no problem answering lots of qu... (more)"

6. Jennifer

I brush my dogs teeth everyday!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

8 repeat clients

"I think that someone who wants to take a job of walking dogs needs to know dogs and their different temperaments. Jennifer is the proud “mother” of two dogs ... (more)"

7. Samantha

Pet Parent's Help

Bridgeport, Chicago, IL, 60609

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

1 repeat client
No Reviews Yet

About: Hello, I'm a big animal lover. Life is always better with furry friends! I have pretty much always had a dog most of my life & always consider the... (more)

8. Krystina

Happy Dogs, Happy Life

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

13 repeat clients

"Krystina was great with Rue! She was only at our house for one night, but still left the apartment cleaner than when we left it. Even when Rue showed her not... (more)"

9. Alex

We'll exercise play safly and enjoy

Hyde Park, Chicago, IL, 60615

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

"I recommend Alex to be a Dog walker and sitter on Rover since he is very punctual and always keeps his commitments. I am sure he will take great care of any ... (more)"

10. Emily

~ Prices Vary ~

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

9 repeat clients

"Emily has helped me with my 3 dogs and 2 cats on such short notice so many times. She came to my house for a week and fed them 2 times a day and went on walk... (more)"

11. Tyler

A day w/ a dog is a day well spent

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

"Tyler has been one of my closest friend's since I came from California to attend college here in Chicago. The first time we went out to eat, we came across s... (more)"

12. Andrea

Dogs love my peaceful personality!

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

"Andrea is a caring, self-motivated, and efficient person who knows how to work productively in stressful and new environments. She has told be about her pass... (more)"

13. Karolina

Karo the Dog Whisperer™

South Loop, CHICAGO, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

13 repeat clients

"Harper loves hanging out with Karolina! She is so amazing and helped us even with a weird schedule (switching off between house sitters while we were on an e... (more)"

14. Emily

I'll run with your dog!

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

About: I am a graduate student at Tufts living just off campus in Medford. I grew up with dogs both big and small, with my most recent pet care experience... (more)

15. Craig

Loving Dog Care In Hyde Park

Hyde Park, Chicago, IL, 60615

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

4 repeat clients

"Craig was very responsive and responsible with a sometimes fluid set of circumstances. We definitely would hire him again. Hi love of dogs makes him a gr... (more)"

16. Jela

Let me watch your fuzzy buddies!

Grand Boulevard, Chicago, IL, 60653

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Je'la is like a dog whisperer, she has a way with animals that can warm even the heart of a non-animal lover. She gives great love and care to all and her he... (more)"

17. Lily

Diligent student with experience

Hyde Park, Chicago, IL, 60637

House Sitting, Drop-In Visits, Dog Walking

"If I would trust anyone with my pet, it would be Lily. She is so responsible and on top of things that I know she would give the utmost care to my dog. Also,... (more)"

Available this weekend
18. Katlyn

Consistent & Flexible :)

Hyde Park, Chicago, IL, 60615

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

4 repeat clients

"Katlyn was great, coming to meet Blue before our trip. Blue loved her and we felt comfortable leaving her to go on our trip. She was very respectful of our a... (more)"

Available this weekend
19. James

Dogs are my favorite people!

Hyde Park, Chicago, IL, 60615

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

"James is phenomenal! He’s very professional, patient and loving when it comes to my 2 year old husky. Very dependable. Him and Sam have really formed a great... (more)"

20. Cortney

Experienced Long-term House/Dog sit

Armour Square, Chicago, IL, 60616

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

"Cortney petsat for me while I was out of town a few times. Not only did she do a great job, it was nice to have piece of mind that someone responsible and tr... (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 eviews from pet owners who have used Rover.