House Sitting in Oakland, Chicago

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

1. Emily

Graduate student and dog lover

Near West Side, Chicago , IL, 60607

House Sitting

"Emily is a very good friend of mine and has been dog sitting for me for about 8 years. She is a very reliable and hard working woman, who has a passion for ... (more)"

2. Catherine

Patient & trustworthy animal lover!

Near West Side, Chicago, IL, 60607

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Thanks! Will hire again. (more)"

3. Jac

Loving and Experienced Pet Sitter

Bridgeport, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

"Jac did a Sunday to Wednesday home stay with Claudia. I appreciate the quick texts and pictures, thank you! I would recommend Jac to anyone and will certainl... (more)"

4. Crystal

Loves all animals

Bridgeport, chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

2 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)"

5. Sabrina

Loving life, but loving dogs more!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Sabrina was amazing with Shadow from the first moment. Although Shadow can be a little hyper at times, Sabrina completely put him at ease. I came home to a h... (more)"

6. Sarah

Will show your pup so much love!!!!

Bridgeport, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"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)"

7. Hailey

I catch the eyes of your dogs!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"We've never had sitter stay at our apartment however wanted Hank to be able to stay within his current environment and didn't want the hassle of taking him/p... (more)"

8. Penelope

Loving dogs more than anything

Lower West Side, Chicago, IL, 60608

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

5 repeat clients

"Penelope was great. We're always nervous leaving the our pups with someone new. She kept us regularly updated throughout the day with photos and messages. W... (more)"

9. Emma

PhD in dog walking & cat cuddling

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

7 repeat clients

"Emma is amazing! Babs absolutely loved her, and she sent me lots of pictures and updates. She followed my instructions exactly and she left the house cleaner... (more)"

10. Krystina

Happy Dogs, Happy Life

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Krystina and Bacon (our furry kid) instantly bonded! This was our first time using Rover and Krystina was very helpful and met with us right away to ease any... (more)"

11. Aasha

I'm a dog loving recent graduate!

Near West Side, Chicago , IL, 60661

House Sitting, Drop-In Visits, Dog Walking

"Aasha is genuinely an animal lover. Her love for animals is unconditional. She easily bonds with animals. In the past, Aasha has offered excellent customer s... (more)"

12. Eliana

Dream big and love dogs!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

"Eliana took good care of our dog and cat while she stayed in our home for an extended week trip. She provided timely updates when I inquired about them throu... (more)"

13. Silvia

Vegetarian/Animal lover/Writer

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Silvia, was awesome! Communication was easy and effective. Plus her experience working at PAWs really made me feel comfortable leaving my 90 lbs, energetic, ... (more)"

14. Brittany

Force-Free and Fun!

Bridgeport, Chicago, IL, 60608

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

"Brittany was so so great! She was extremely flexible, quick to respond, and kept me updated throughout Royal's stay with her. It was clear Brittany was very ... (more)"

15. Rory

I love and appreciate all pups

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Rory was fantastic and was my first sitter via Rover. She took a last minute job with me (same day for a 3 day long overnight) and was great! I was comfortab... (more)"

16. LeAnna

10+ years of Professional Pet Care!

Hyde Park, Chicago, IL, 60615

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

"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. Christina

Calm, warm hearted dog lover

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"Christina is terrific! She has become our regular dog-sitter when we are away for the night. She shows up on time, confirms everything upon arrival, sends no... (more)"

18. Emily

Experienced Sitter in Chicago!

Lower West Side, Chicago, IL, 60608

Dog Boarding, Drop-In Visits, House Sitting

1 repeat client

"Emily was great. She picked our dog up early to help us with our travel arrangements, she sent lots of photo updates and checked in frequently. I felt like m... (more)"

19. Grace

Excited to meet your pup!

Woodlawn, Chicago, IL, 60637

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Grace stayed with my dogs over Thanksgiving. They seemed to be happy upon my return. Thanks for taking care of them! (more)"

20. Collin

Gentle Soul, Love Animals, Reliable

Near South Side, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

"Collin Sanderson is s very responsible dependable young man. He is also very loving, sincere and compassionate in every aspect of his life. I would trust him... (more)"

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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.

Want to be added to this list of sitters in Chicago? Become a pet sitter or dog walker on Rover.

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.