House Sitting in Oakland, Chicago

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

1. Catherine

Patient & trustworthy animal lover!

Near West Side, Chicago, IL, 60607

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"This was our first time hiring a pet sitter and Catherine was amazing! Both animals were well taken care and we could not be more pleased! Will definitely be... (more)"

2. Simone

Professional Pup Lover!

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Hello, Rover! Simone has cared for my pup, Honey on several occasions & I have never come home to an unhappy pet! She is kind and where Honey is concerned... (more)"

3. Jac

Loving and Experienced Pet Sitter

Bridgeport, Chicago, IL, 60608

House Sitting, Drop-In Visits

2 repeat clients

"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 is a WONDERFUL, WONDERFUL puppysitter. Atticus had a blast and has been waiting for Sabrina to come back and play ever since. Sabrina was caring, pla... (more)"

6. Collin

Gentle Soul, Love Animals, Reliable

Near South Side, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Collin is my first experience with Rover and I couldn't be more pleased. Using Rover came with short notice and I worried that would create a problem. Coll... (more)"

7. Silvia

Vegetarian/Animal lover/Writer

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Sylvia was an outstanding, conscientious, and very caring dog and house sitter. We would trust her any time with both our dog and our home. Highly recommended! (more)"

8. Nellie

Graduate student who loves dogs :)

Near South Side, Chicago, IL, 60616

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

"I hired Nellie to watch my two dogs while I was out of town on a work trip, my dogs are not actual dogs to me they are basically my children, so, I am super ... (more)"

9. Penelope

Loving dogs more than anything

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

9 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. Ashleigh

Dog loving student in Chi

Near South Side, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"My husband and I are new dog parents and were going out of town for a few days, leaving our pup for the first time ever. Ashleigh stayed at our place taking ... (more)"

11. Sarah

Will show your pup so much love!!!!

Bridgeport, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Sarah is a loving, enthusiastic dog caregiver who I have trusted with my beloved French Bulldog, Pablo several times in the past. She is very responsible an... (more)"

12. Emma

PhD in dog walking & cat cuddling

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

7 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)"

13. Brittany

Force-Free and Fun!

Bridgeport, Chicago, IL, 60608

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

1 repeat client

"We LOVE Brittany! She took care of Miko with a lot of love and care while were out on a 14 day trip. She stayed in our house, took care of Miko and our home.... (more)"

14. 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)"

15. Isabel

Reliable Sitter - Flexible Schedule

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Like many Chicagoland dog owners, I was seeking someone that would offer the tender loving care of my dog Cookie in my absence as I went on business trips. I... (more)"

16. Christina

Calm, warm hearted dog lover

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"Christina took excellent care of my pup while I was away for a long weekend. She communicated regularly and handled small requests, no problem! Will definite... (more)"

17. Krystina

Happy Dogs, Happy Life

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"Krystina was amazing. I don't think my dog missed me a bit as she seemed so loved when I got home. Krystina even gave Sophie a bath when I was gone because S... (more)"

18. 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)"

19. Danielle

graduate student who loves doggies!

Hyde Park, Chicago, IL, 60615

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

7 repeat clients

"Amazing, Hendrix seemed to love his vacay away from me as much as I enjoyed my vacation. Sent me updates and pictures while I was gone and when my flight got... (more)"

20. Paige

My name is Paige & I'm a dogaholic.

Hyde Park, Chicago, IL, 60615

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

"Paige is very caring and patient with dogs. She has rescue dogs of her own and one with behavioral problems. She has been very patient in caring in helping t... (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.