House Sitting in Oakland, Chicago

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

1. Payal

West Town Pet Sitter

McKinley Park, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

22 repeat clients

"Payal was excellent--took great care of my babies and was very communicative, which I appreciated. I would absolutely recommend her and book again! (more)"

Confirmed President's Day Availability
2. Craig

Loving Dog Care In Hyde Park

Hyde Park, Chicago, IL, 60615

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

"I have come to know Craig as a good and caring person. I have witnessed him interacting with dogs on several occasions and he has displayed genuine concern f... (more)"

3. Sandra

Full time dog lover!

Lower West Side, Chicgao, IL, 60608

House Sitting

"We had a wonderful experience with Sandra. She was able to accommodate an extremely last minute request to house/dog sit for the weekend for us. She sent reg... (more)"

4. Robert

All furry friends welcome!

Loop, Chicago, IL, 60601

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

34 repeat clients

"Robert was great, he even arrived with treats in his pockets for Coco & Smokey! Always responded promptly and is very qualified, friendly and reliable! We wi... (more)"

Confirmed President's Day Availability
5. Karolina

Karo the Dog Whisperer™

South Loop, CHICAGO, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

13 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)"

6. Yovana

Your dog's life shouldn't be ruff!

New City, Chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

"Hi, my name is Jennifer Chou. I've known Yovana for about a year now, and she takes care of my corgi over the weekend. She always makes time to fit my schedu... (more)"

7. Allison

Certified Veterinary Technician

Bridgeport, Chicago, IL, 60609

House Sitting, Drop-In Visits

7 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)"

8. Krystina

Happy Dogs, Happy Life

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

12 repeat clients

"This was the second time I had Krystina stay at my home with my dog Sophie. Everything went great and I don't think Sophie missed me that much :( Ha (more)"

9. Enoch

Dogs/cats/other pets welcomed!

Bridgeport, Chicago, IL, 60608

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

17 repeat clients

"Although Rocco takes a while to warm up to strangers, he was quick to come up to Enoch and wag his little nub at the first meet and greet. That initial meet... (more)"

10. Elizabeth

Owned & worked w/ dogs all my life!

Bridgeport, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

"Very pleased with the compassion, care and attentiveness that Liz has shown for my Bella. Liz was recommended by another great Rover walker. Due to my hectic... (more)"

Confirmed President's Day Availability
11. Stacey

I Love Animals and Animals Love Me

Douglas, Chicago, IL, 60616

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

1 repeat client

"We ( husband, wife and dog) found Stacey very reliable and accessible. The whole experience made our time away stressless. Thanks (more)"

12. Josh

Any dog out there is family to me.

Douglas, Chicago, IL, 60653

House Sitting, Drop-In Visits, Dog Walking

"He's been really helpful and my dog adores him. I give him a two thumbs up because he's patient like nobody's business. Thank you Josh for being the champ as... (more)"

13. Amanda

Animal loving college student

Near South Side, Chicago, IL, 60616

Dog Boarding, House Sitting

1 repeat client

"Amanda is experienced and good sitter. She is able to work around the crazy schedules and take good care of my pup (more)"

14. Collin

Gentle Soul, Love Animals, Reliable

Near South Side, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

7 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)"

Confirmed President's Day Availability
15. Andrew

Can't wait to meet your Pup!

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Andrew regularly texted and sent photos. He was super reassuring that Archie was doing well also and left my house as clean as when he arrived. I would HIG... (more)"

Confirmed President's Day Availability
16. Nathan

A Heartbeat At My Feet!

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

"To Whom It May Concern: It is my pleasure to provide a reference for Nathan. He has always been very comfortable with all of my dogs as well as my famil... (more)"

17. Emily

I'll run with your dog!

Hyde Park, Chicago, IL, 60615

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

About: I am a graduate of the University of Chicago working and living in Hyde Park. I grew up with dogs both big and small, with my most recent pet care ... (more)

18. Jacob

A fun, caring and creative person

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"When I went to Miami Jacob took good care of my miniature pincher called Marley Moe. Jacob never failed to follow Marley's daily scheduled activities which ... (more)"

19. 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)"

20. Alex

I'll run with your dog, South Loop!

Douglas, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

About: My name is Alex and I've been taking care of my friends and family's dogs for over 4 years now. I've taken care of dogs that are super energetic su... (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.