House Sitting in Oakland, 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.
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1. Kat

Quality care for our fur babies

Lower West Side, Chicago, IL, 60608

House Sitting

"I was really drawn to Kat's relaxed and yet attentive attitude towards my dog and 3 cats. She was great about keeping me updated and sending pics everyday wh... (more)"

2. Karolina

Karo the Dog Whispererâ„¢

South Loop, CHICAGO, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

10 repeat clients

"Karolina was amazing! We had some totally unexpected and very annoying apartment maintenance work done during Karolina's stay-- our floors had to be almost c... (more)"

3. Krystina

Happy Dogs, Happy Life

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

10 repeat clients

"Krystina was such a great sitter! She was flexible in coming over to meet me and June beforehand, and checked in several times throughout the weekend with te... (more)"

4. Mikayla

Energetic dog-lover

Woodlawn, Chicago, IL, 60637

House Sitting, Dog Walking

1 repeat client

"Mikayla was great. Sparky had lots of fun with her, we could tell. Mikayla shared pictures which we appreciated. We will use Mikayla again. (more)"

5. Catherine

Patient & trustworthy animal lover!

Near West Side, Chicago, IL, 60607

House Sitting, Dog Walking

6 repeat clients

"We used Catherine for a second time and she was exceptional! She was very flexible, arriving early for a morning walk and staying late because our flight wa... (more)"

6. Jeanne

Jeanne's Pawsome Animal Care

Kenwood, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

About: Full time student looking to spend some time with this city's amazing furry friends. I've had dogs and cats all my life and am comfortable caring f... (more)

7. Collin

Gentle Soul, Love Animals, Reliable

Near South Side, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"Collin was fantastic. Super professional, communicative, and very caring. Lulu and Bolt loved him. I felt very comfortable and confident that my pups were in... (more)"

8. Eleanor

Because it really is my pleasure :)

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Eleanor did a great job watching Buddha and my home while away on business. She was very communicative and sent a bunch of pictures along with her texts. I t... (more)"

9. Liz

Flat rate for any number of pets!

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits

2 repeat clients

"First off, just want to say how much we appreciate Liz being available on such short notice and for a holiday weekend!! My bf and I decided to try and make a... (more)"

10. Alison

Your dog needs a walking partner

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

"Alison has a big heart for dogs and animals. She will go out of her way to make sure any animal is taken care of and looked after. Alison took care of my dog... (more)"

11. Penelope

Loving dogs more than anything

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

20 repeat clients

"Penelope stayed with my 10-week old GSD for two nights while I was traveling for work. This was my first time using Rover and being away from my pup and Pene... (more)"

12. Anita

Goal in Life: Play with Dogs

Bridgeport, Chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

"Anita has a lot of experience caring for animals, having been a dog sitter during her college years. I have first handedly seen the way that Anita cares deep... (more)"

13. Kathryn

Every dog must have his day!

Kenwood, Chicago, IL, 60653

House Sitting, Drop-In Visits, Dog Walking

"Kathryn is an excellent, responsible, and caring sitter! She took care of my high-maintenance and very energetic border collie/pointer/lab/hound mix for a we... (more)"

14. Taylor

Your dog's new best friend!

Loop, Chicago, IL, 60605

House Sitting, Doggy Day Care, Dog Walking

1 repeat client

"Taylor was great with Mocha! She gave numerous updates throughout her stay and left our condo just as she found it. Our puppy was very sleepy from all the ... (more)"

Available this weekend
15. Crystal

Loves all animals

Bridgeport, chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Crystals was great. Very responsive when communicating. Very reliable and professional. And Sassy loved her! We hate to leave town, but it's nice to know tha... (more)"

16. LeAnna

10+ years of Professional Pet Care!

Hyde Park, Chicago, IL, 60615

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

1 repeat client

"Our experience with LeAnna was wonderful! She took perfect care of our dog and cat and kept us updated throughout the stay. She really listened and We are co... (more)"

17. Audrey

Dogs are my life!

Bridgeport, Chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

"Audrey was awesome with my two boys. She took the time to come meet me and them before scheduling her stay. She asked really great questions and cared a lot ... (more)"

18. Gabrielle

Dog friendly home

Hyde Park, Chicago, IL, 60615

Dog Boarding, House Sitting

About: As a student with a dog of my own, I've gone through numerous rounds of various kind of training! From potty training, to simple basic obedience tr... (more)

19. Alexandra

Loving sitter in the city.

Bridgeport, Chgo, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

18 repeat clients

"Lexy did a great job with our dog Lennie! He loved her when he first met Lexy, so we knew he was in good hands. After our trip he seemed very happy and healt... (more)"

20. Allison

Certified Veterinary Technician

Bridgeport, Chicago, IL, 60609

House Sitting, Drop-In Visits

5 repeat clients

"Allison is hands down the best pet sitter! We had her stay in our home over a long weekend with our two senior pups. She provided excellent communication and... (more)"

Experience exceptional service and a personalized match

From start to finish, we'll handle all the details for you.

Learn About Premier

With over 140,000 pet and house sitters on Rover.com, you can easily find house sitting near you.

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.