Pet Sitting & 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.

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1. Megan Verified Background Check

I am very passionate about animals!

Loop, Chicago, IL, 60605

Drop-In Visits, Dog Walking

"Megan watched our golden doodle puppy for two weeks and did an amazing job. She is a gem! She followed feeding and potty training instructions to a tee. I de... (more)"

2. Elizabeth Verified Background CheckRover 101

Animal Loving Family

Grand Boulevard, Chicago, IL, 60653

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

"She was great! Took great care of our big, energetic dog. Would definitely book again (more)"

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3. Michael Verified Enhanced Background CheckRover 101

Always at Home & Right by Dog Park!

Near South Side, Chicago, IL, 60616

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

"Michael is an honest, responsible, and trustworthy person. Anytime I need someone to watch my two dogs, I always check to see if Michael is available. He is ... (more)"

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4. Michael Verified Enhanced Background Check

I treat your pet like it’s mine.

Near South Side, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Mike is awesome! He came over for a meet & greet and Javi instantly loved him. He’s very kind & it’s clear he truly loves his jobs & all the pups he sees! I ... (more)"

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5. Khala Verified Background Check

I Might love your dog more !!!

Woodlawn, Chicago, IL, 60637

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

"Khala has been taking care of my pug, Lily Grace, for three years. I trust her completely. Although when I come to pick Lily Grace up, she doesn't always w... (more)"

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6. Elliott Verified Background Check

Marketer by day, Dog lover 4 Life!

Washington Park, Chicago, IL, 60609

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

"Elliot was fantastic! He took great care of our Chow Chow for a week while we were out of the country. She's 11 and can sometimes be a bit temperamental but ... (more)"

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7. Alyssa Verified Enhanced Background Check

Pet lover looking to help ❤️

New City, Chicago, IL, 60609

Drop-In Visits, Dog Walking

"Alyssa is such a sweet person. She treats every animals, whether it's a fish or a dog, with the most respect. She is very passionate about animals. She makes... (more)"

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8. christine Verified Background Check

Walk and Bark!

Douglas, Chicago, IL, 60616

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

"Christine was very punctual and professional. I would highly recommend her to look after your fur babies! (more)"

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9. Emily Verified Background Check

Experience with multiple sized dogs

Bridgeport, Chicago, IL, 60616

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

About: I am a student from Chicago currently studying at UIUC. I have lots of free time over the summer and will be able to spend a lot of time and give t... (more)

10. Crystal Verified Background Check

Loves all animals

Bridgeport, chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

"I am so happy I found Crystal. It is my second time hiring her to check in on my bunny when I was out of town and she does an exceptional job and I definitel... (more)"

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11. Jasmine Verified Enhanced Background Check

Plenty of long walks and treats!

Bridgeport, Chicago, IL, 60609

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

"For as long as I've known Jasmine, she has always been loving and caring toward dogs. She goes out of her way to show compassion to the dogs she interacts wi... (more)"

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12. Sandra Verified Background Check

Ready to meet Pawsome Friends

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Sandra is a very kind, wonderful, responsible person who will take great care of your pets! There are very few people I would trust with my dog Quincy, but I... (more)"

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13. Masheika Verified Background CheckRover 101

Crazy cat lady who loves dogs!

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

"I was nervous about leaving a newly adopted dog and my 12 year old senior with someone so I did drop in visits and walks. Masheika was great with these two. ... (more)"

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14. Kristina Verified Enhanced Background Check

Life is more fun with furry friends

Hyde Park, Chicago, IL, 60615

Drop-In Visits, Dog Walking

"Kristina was a great cat-sitter. This is the first time we've come home from a trip that they haven't been annoyed with us. She sent lots of pictures. It was... (more)"

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15. Marckenley Verified Background Check

Let me take care of your dog

Douglas, Chicago, IL, 60616

Dog Boarding, Drop-In Visits, Dog Walking

"Kenno is by far the best sitter that I’ve had for my dog. He was great about giving updates while I was gone and provided pictures as well. He was great with... (more)"

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16. Shannon Verified Background Check

The Trust-Worthy Dog Sitter/Walker

Kenwood, Chicago, IL, 60653

House Sitting, Drop-In Visits, Dog Walking

"Shannon has walked my dog before when i couldn’t. She is an excellent person to dog sit or dog walk. She took pictures of the dog throughout the walk and als... (more)"

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17. Katja Verified Background Check

Over 10 years of dog experience!

Grand Boulevard, Chicago, IL, 60653

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

"Katja was kind, considerate, and communicative. Having her with our cats was a huge relief and we look forward to booking her services in the future! (more)"

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18. Tina Verified Background Check

Our pets become our family <3

Kenwood, Chicago, IL, 60615

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

About: I have always worked with animals ever since I was a child. I enjoy getting to know their personalities and know how difficult it can be to find s... (more)

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19. Qiana Verified Enhanced Background Check

Dog lover, Lots of time on weekends

Douglas, Chicago, IL, 60605

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

"Qiana is a kind, gentle and loving person. I've seen her with a few dogs, one of which was her own and she referred to him as her baby. Although she is kind ... (more)"

20. Kathleen Verified Background Check

Some of the best people I know...

Kenwood, Chicago, IL, 60615

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

"Kathleen G is, seriously, the biggest pet lover I have ever known. She had a wonderful, beautiful dog who passed away last year at age 15. Kathleen cared and... (more)"

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: