Pet Setting & Drop Ins in Oakland, Chicago

Book a pet sitter to stop by your home a few times a day to feed and play with your dog.

1. Ashleigh

Dog loving student in Chi

Near South Side, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

7 repeat clients

"Ashleigh has been awesome and so flexible and accommodating to my last minute requests and crazy schedule. It's so great to have the same person be able to c... (more)"

2. Penelope

Loving dogs more than anything

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

16 repeat clients

"Penelope is fantastic!! She took excellent care of our pets. Her communication was great and no reasonable request was denied. We strongly recommend her serv... (more)"

3. Abby

Experienced Sitter Loves All Pets!

Douglas, Chicago, IL, 60616

Drop-In Visits, Dog Walking

11 repeat clients

"Absolutely excellent! She was available same-day within the hour -- she is awesome. Highly recommended! (more)"

Confirmed Easter Weekend Availability
4. Sidney

Experienced & Active Dog Enthusiast

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"I can attest to Sidney's abilities as a responsible and loving dog caregiver. Sidney has cared for my elderly dog, who had many health problems at the time. ... (more)"

5. Breana

Dogs are my favorite people.

Hyde Park, Chicago, IL, 60615

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

1 repeat client

"Breana was a great cat sitter. She sent daily rover cards and made sure my cats had fresh food and water. She also played with them a bit. Definitely will bo... (more)"

6. Netiya

Caring for others is my passion.

Bridgeport, Chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Netiya watched my cat, Harvey, while I was away on an extended weekend. She updated me with photos and messages! Would definitely use Netiya and her services... (more)"

7. Collin

Gentle Soul, Love Animals, Reliable

Near South Side, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"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)"

8. Danielle

graduate student who loves doggies!

Hyde Park, Chicago, IL, 60615

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

8 repeat clients

"Danielle is a lover of all animals. She is always taking pictures of dogs and cats, and is a great cat mommy. She really is so in love with her Zeus, it is a... (more)"

Confirmed Easter Weekend Availability
9. Maia

Cubby Loves Puppies

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"To say your pet is in good hands with Maia is an understatement. She is an extremely capable and reliable pet sitter. She's caring and very experienced with ... (more)"

10. Mia

Best Care for Your Best Friend

Loop, Chicago, IL, 60605

Drop-In Visits, Dog Walking

"Mia was so wonderful to work with. This was our first time using Rover and had to find someone very last minute. Mia was quick to respond and great at commun... (more)"

11. Moesha

College student that loves Dogs!

Douglas, chicago, IL, 60616

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

3 repeat clients

"Moesha was great with a little doggie who is mostly afraid of people. Little Jax warmed up to her and she took great care of him. 5 Paws for Moesha (more)"

12. Emma

PhD in dog walking & cat cuddling

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

7 repeat clients

"Emma was incredibly accommodating; offered to come over for a meet and greet so I could show her around, and we could chat through the stay. She worked with ... (more)"

13. Mindy

5-Star Care Custom-Tailored Stays

Douglas, Chicago, IL, 60616

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

About: My 1890's rowhouse with 3,300 sq. ft. and fenced front and back yards will be a perfect home to assure a safe and enjoyable stay for your four-legg... (more)

14. Jac

Loving and Experienced Pet Sitter

Bridgeport, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Jac looked after my sweet corgi, Oliver, while I went away for a weekend. She took amazing care of him! She even sent little pictures of them having fun toge... (more)"

Confirmed Easter Weekend Availability
15. Courtney

Best Belly Rubber in Town!

Kenwood, Chicago, IL, 60615

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

3 repeat clients

"Courtney was absolutely fabulous! She was great with Louie and Aurora - both dogs told us so! And she was great with us, keeping in touch with just the right... (more)"

16. Sam

Improving lives, one dog at a time

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"She's amazing. She had no trouble with my kitten. He isn't used to people but he had no trouble warming up to Sam. She even brought packages inside and manag... (more)"

17. Emily

Experienced Sitter in Chicago!

Lower West Side, Chicago, IL, 60608

Dog Boarding, House Sitting, Drop-In Visits

1 repeat client

" Emily has been in the dog-caretaking business for four years. There is nobody I'd recommend before her. Not only is she extremely trustworthy on all levels... (more)"

18. Brittany

Force-Free and Fun!

Bridgeport, Chicago, IL, 60608

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

3 repeat clients

"Brittany is great! Thanks for taking care of our pup ? (more)"

19. Crystal

Loves all animals

Bridgeport, chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

About: I have 14 years experience with a variety of animals, including exotics. I have taken care of animals with special needs and medications. While i... (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 is wonderful with dogs. She is very attentive to her own fur babies and I know she would treat your pup like her own. She is very kind and has a wonder... (more)"

Experience exceptional service and a personalized match

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

Learn About Premier

Dog lovers in Oakland, Chicago, IL love pet sitters on Rover.com. Over 7,915 pet owners have reviewed pet sitters on Rover in Chicago, giving them an average rating of 4.9/5 stars. No matter what your price range is, you might be surprised to learn how affordable pet sitting in Chicago can be when you book with Rover. Wondering how much it might cost to book pet sitting? Check out our average pet sitting rates to get an idea before contacting a pet sitter near you.

Never beg a friend to drop in on your pets while you're on vacation again. With Rover, you can find the perfect Oakland, Chicago pet sitter in seconds. Sitters on Rover are pet lovers, who will be happy to sit dogs, cats, caged pets, and even horses while they take care of your home. By removing common pet care obstacles, Rover ensures pets nationwide are happy and well-cared for even when their human is away, and empowers pet lovers to live happy and fulfilling lives. Founded on the belief that everyone should have the opportunity to experience the unconditional love of a pet, Rover makes it easy for you to reach trusted pet sitters in Oakland, Chicago who can provide the care your pet needs, when they need it.

A Daily Treat: A Blog by Rover

Rover's got you covered, even when you don't need a dog sitter. Check out our blog for pictures of adorable dogs, help on your biggest dog-related questions, and more:

Book a Stay, Donate to a Cause

Sit a Dog, Save a Life lets you raise money for local dogs-in-need by doing something you do already: asking your neighbors to watch your dog instead of leaving them in a kennel. Many Rover sitters in Oakland, Chicago donate a percentage of their earnings to nonprofits through Sit a Dog, Save a Life. When you book with a sitter who has the Rover Donation Badge on their profile, you're helping dogs in need, right here in Chicago.

We're proud to support over 200 organizations across the nation, including: