House Sitting in Oakland, Chicago

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

1. Collin

Gentle Soul, Love Animals, Reliable

Near South Side, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

4 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)"

2. Ashleigh

Dog loving student in Chi

Near South Side, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

7 repeat clients

"Ashleigh was absolutely wonderful. We spent a week away from both of our sweet dachshunds and she made sure to keep us up to date with pictures every day. Bo... (more)"

Confirmed Easter Weekend Availability
3. 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)"

4. Catherine

Patient & trustworthy animal lover!

Near West Side, Chicago, IL, 60607

House Sitting, Drop-In Visits, Dog Walking

5 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)"

5. Aasha

I'm a dog loving recent graduate!

Near West Side, Chicago , IL, 60661

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Aasha was amazing with Nova. Puppies can be hard but she made sure to take her out often and take her on long walks and to the dog park to tire her out. She... (more)"

6. Emily

Graduate student and dog lover

Near West Side, Chicago , IL, 60607

House Sitting

"Emily was great! She stayed at our house while watching our dog. She is very responsible, reliable and neat. She sent pictures of our dog everyday and is a g... (more)"

Confirmed Easter Weekend Availability
7. Sidney

Experienced & Active Dog Enthusiast

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Sidney was great with our dog! She was able to come last minute and kept him happy! She even came with some treats for him. We will reach out to her again. (more)"

8. 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)"

9. Jac

Loving and Experienced Pet Sitter

Bridgeport, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Jac was great. She came over to meet our 2 big dogs and they got along swimmingly. She was communicative and easy to reach when I wanted to check in. I would... (more)"

10. 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)"

11. Brittany

Force-Free and Fun!

Bridgeport, Chicago, IL, 60608

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

3 repeat clients

"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)"

12. Allison

Certified Veterinary Technician

Bridgeport, Chicago, IL, 60609

House Sitting, Drop-In Visits

3 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)"

13. Eliana

Dream big and love dogs!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Eliana was a huge help in watching Grey last minute after our original sitter fell through. She showed up early to our place and met with Grey. She responded... (more)"

14. Penelope

Loving dogs more than anything

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

16 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)"

15. 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)"

16. 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)"

Confirmed Easter Weekend Availability
17. Hayley

Flexible, reliable, and available!

Bridgeport, Chicago , IL, 60608

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"My wife and needed some help with our pooches when we were in the hospital welcoming our daughter. Hayley met us the night before my wife went to labor, and ... (more)"

18. Emily

Experienced Sitter in Chicago!

Lower West Side, Chicago, IL, 60608

Dog Boarding, House Sitting, Drop-In Visits

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. Ida

A home away from home

Bridgeport, Chicago, IL, 60609

Dog Boarding, House Sitting

2 repeat clients

"Ida responded to my post on the internet very quickly and professionally when I needed a last minute dog-sitter. Ida agreed to take care of my sweet old corg... (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

1 repeat client

"Paige would take great care of your dogs! She is dependable, trustworthy and experienced. She owns two dogs of her own. You will feel very comfortable leavin... (more)"

Experience exceptional service and a personalized match

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

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.

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.