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.

Confirmed availability
Memorial day
1. Joy

Your Dog Will Be Loved!

South Shore, chicago, IL, 60610

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

6 repeat clients

"Joy is awesome! She was punctual and when I needed her to assist me with my Rupert for an emergency she didn’t hesitate to respond and help. She sent picture... (more)"

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2. Ivana

College student who loves dogs!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

13 repeat clients

"She was very timely and sent me pictures of the dog which eased my mind while I was gone! I will definitely rebook Ivana! (more)"

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3. Karolina

Karo the Dog Whisperer™

South Loop, CHICAGO, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

14 repeat clients

"Karolina stays in touch and shows that she truly cares for your pets - it helps so much when you are away! I get notes and photos constantly. I would highly ... (more)"

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4. Dee

Hyde Park Dog Lover

Kenwood, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

"Dee is THE best doggie caretaker I’ve ever encountered! She truly loves dogs and is responsible and fun. My dog has a Fitbark so I can track her steps and I ... (more)"

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5. Britney

Cozy Home, Large Backyard & LOVE?

Bridgeport, Chicago, IL, 60608

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

About: I am FOR SURE an Animal Lover. Growing up with a house full of cats and dogs (even had a ferret) my experience goes back far. I love taking care of... (more)

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6. Tina

Loving Personal Care Assistant

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

8 repeat clients

"Tina was wonderful with Brady! She is responsible and sweet and sent me the cutest pics of Brady! This was my first time using Rover and I'm so happy to have... (more)"

Confirmed availability
Memorial day
7. Alex

We'll exercise play safly and enjoy

Hyde Park, Chicago, IL, 60615

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

"Alex was fantastic! He went the extra mile for us, patiently waiting for me to drive to our house when there was an issue with gaining entry. Koffee quickly ... (more)"

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8. Kristin

Long walks and lots of love!

Bridgeport, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

About: My family was always a huge fan of dogs of all sizes, from German Sheppards to Bull Terriers, and even the stray Bichon Frise! I have been raised a... (more)

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9. Christal

I’m @ home full time

Kenwood, Chicago, IL, 60615

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

About: Hi, I’m Christal and I am looking forward to being your next pet-sitter! I walked dogs professionally for years and have recently picked it back up... (more)

Confirmed availability
Memorial day
10. Enoch

Rover Sitter/Boarder ~SINCE 2015!

Bridgeport, Chicago, IL, 60608

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

23 repeat clients

"Enoch is a very responsible sitter! He takes care of my cats very well. Feed them exactly how much it needs to! He plays with them, brushes their hairs and s... (more)"

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11. Ekaterina

Home full-time - fenced yard

Bridgeport, CHICAGO, IL, 60608

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

"Ekaterina is amazing with dogs! She is loving and has a great energy that my pups adore. She helped me with occasional walks and extended boarding many times... (more)"

Confirmed availability
Memorial day
12. Margot

Keeping those tails wagging!

Kenwood, Chicago, IL, 60615

Drop-In Visits, Dog Walking

"Margot did a wonderful job watching my somewhat high maintenance senior dog, Walle. Walle has special needs including scheduled medications, as needed medica... (more)"

Confirmed availability
Memorial day
13. Crystal

Loves all animals

Bridgeport, chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"Crystal is the ideal cat sitter, she loves animals and I had no doubt my cat was in caring hands while I was out of town. (more)"

Confirmed availability
Memorial day
14. Tara

Care for your dog like my own

Bridgeport, Chicago, IL, 60616

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

"Tara took care of my dog Mindy and cat Gonzo over the weekends I was away for work. She sent updates and pictures which I really loved to keep in touch with ... (more)"

Confirmed availability
Memorial day
15. Nina

Student & home often, love to run!

Hyde Park, Chicago, IL, 60637

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

"Nina took good care of my two cats while I was on Vacation in Florida for a week! She is very reliable. (more)"

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16. Rachel

College student loves dogs!

Douglas, Chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Rachel has watched my family's dogs on several occasions. She takes amazing care of them and each time we come home after a long trip they whine at the door ... (more)"

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17. Samantha + Mac

Looking for new friends!

Hyde Park, Chicago, IL, 60615

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

"I have known Samantha for over 15 years and pets have always been a part of her life, both dogs and cats. Her pets have always been very happy, well-trained... (more)"

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18. Eve

dog lover :)

Kenwood, Chicago, IL, 60615

Drop-In Visits, Dog Walking

"Eve is wonderful with dogs, I have never met a dog that was not naturally drawn to her. She is incredibly responsible and patient, with excellent animal skil... (more)"

Confirmed availability
Memorial day
19. Mark

Caring And Diligent Care-Taking

Douglas, Chicago, IL, 60616

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

About: Punctual, diligent, caring, and open to any needs your buddy might have. I've grown up around and have owned and loved all breeds. I can care for l... (more)

Confirmed availability
Memorial day
20. Nisha

Home full time. Dog lover!

Douglas, Chicago, IL, 60616

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

About: Full time masters student who loves pets especially dogs. Would like to get a dog someday after I finish my education. I love going on walks and ta... (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: