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. Catherine

Patient & trustworthy animal lover!

Near West Side, Chicago, IL, 60607

House Sitting, Drop-In Visits, 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)"

Available this weekend
2. Jamey

Fun and compassionate caretaker!

Woodlawn, Chicago, IL, 60637

House Sitting, Drop-In Visits, Dog Walking

"Jamey a watched my dog multiple times over the years. My dog can get really anxious when we leave and one time we went on a long trip where he got sick. Jame... (more)"

3. Mary

Caring Dog Walker Available

Near South Side, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

"I have known Mary to be very empathetic and playful with animals. She has a background knowledge in what it takes to be a loving caregiver to her own pets a... (more)"

4. Rebecca

Your dogs new pal and confidant

Lower West Side, Chicago, IL, 60608

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

"Rebecca is a thoughtful and enthusiastic dog-sitter! She took care of my dogs Walter and Reese for a week while we were on vacation and left them happy, heal... (more)"

5. Krista

Flexible schedule, love dogs

Hyde Park, Chicago, IL, 60615

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

About: Other dog owners describe me as a caring, responsible, loving dog lover and pet sitter. I'm a current grad student so I have a flexible schedule to... (more)

6. 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)"

7. Jory

Dog lover on the go!

Near West Side, Chicago, IL, 60612

House Sitting, Drop-In Visits

1 repeat client

"Jory is a caring and wonderful friend to our beloved pet. He takes the time to know our dog and care for her while we are away. I would recommend Jory for ... (more)"

8. KC

Loving Pet Sitter/Nursing Student

Near West Side, Chicago, IL, 60607

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"KC watched our 4 month old puppy, George, while we were away for the first time since we brought him home. I was so nervous leaving our little guy behind, bu... (more)"

9. Penelope

Loving dogs more than anything

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

17 repeat clients

"Penelope has fast become our go-to dog sitter. She has a great, patient, calming approach with dogs that is especially important with little, skittish ones,... (more)"

10. 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)"

11. Myk'La

Mind, face, and soul of a pup

Hyde Park, Chicago, IL, 60637

House Sitting, Drop-In Visits, Dog Walking

"Myk'La is a awesome person and some one i'd highly recommended for the Dog Caregiver position.She posess a high spirit personality along with an outgoing and... (more)"

12. Karolina

Karo the Dog Whispererâ„¢

South Loop, CHICAGO, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"Karolina was very caring and attentive to my senior girl. I will definitely use her again! (more)"

13. Crystal

Loves all animals

Bridgeport, chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"I could not have asked for a better sitter than Crystal. She came over prior to the start of service to meet my dog and I could tell at once that she was tru... (more)"

14. Simone

Professional Pup Lover!

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Simone is a wonderful person and caregiver. Whenever I have Simone petsit for my dog & cats, I am always kept updated on how my babies are doing, and feel 10... (more)"

15. 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)"

16. Emma

PhD in dog walking & cat cuddling

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

9 repeat clients

"I highly recommend Emma. Our household is big and crazy and she held her own :-) She sent lots of pictures and updates so we didn't have to worry about our k... (more)"

17. Sarah

Will show your pup so much love!!!!

Bridgeport, Chicago, IL, 60608

House Sitting, Dog Walking

2 repeat clients

"Sarah is an angel! She loves my sweet baby Ray like one of her own. Sarah has watched Ray on multiple occasions. During their time together she often takes h... (more)"

18. Mary

Mary's Pet Care

South Side, Chicago, IL, 60616

House Sitting

5 repeat clients

"Mary did a fantastic job sitting for my dog Huck while I was away on a work trip. She sent text updates and pictures at least once a day. She even brushed ... (more)"

19. Alexandra

Loving sitter in the city.

Bridgeport, Chgo, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

18 repeat clients

"This was our first try with Rover and Alexandra was our first sitter. Boy, did we pick a winner! One of our dogs is skittish with strangers yet she warmed r... (more)"

20. 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)"

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Learn About Premier

Home owners love Chicago house sitters on Rover. 9,532 owners have reviewed sitters in the Chicago, IL metro area, giving them an average rating of 4.9/5.

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.