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. Jennifer Verified Background CheckRover 101

Architect by day, Dog lover 4 life!

Hyde Park, Chicago, IL, 60615

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

"Jen is awesome, she’s so real and down to earth. She actually cares about my pets (sent me pictures, was willing to work with me when she couldn’t get ahold ... (more)"

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2. Angelica Verified Background Check

Flexible schedule, love all pets!

Near South Side, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Angelica was fantastic helping us out during a busy week. She took tremendous care of our 11 week old golden retriever puppy, attending to his needs as they ... (more)"

3. Andrea Verified Background CheckRover 101

Fun times waiting to be had!

Washington Park, Chicago, IL, 60637

House Sitting, Drop-In Visits, Dog Walking

"Andy did a fantastic job befriending my demanding rescue kitty who doesn’t automatically understand people are his friends. Yet while I was away, Andy patien... (more)"

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4. Elaina Verified Enhanced Background Check

Animals live in my soul

Near West Side, Chicago, IL, 60661

Drop-In Visits, Dog Walking

"Elaina was a fantastic sitter for my cat while I was away for 2 weeks and I can't recommend her enough for the care of any animal! Great communication, detai... (more)"

5. Rachel Verified Enhanced Background Check

Gaurenteed to have a doggone time

Lower West Side, Chicago, IL, 60608

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

"Rachel did a great job with drop in visits for our night out of town. She communicated well and has clearly spent a good deal of time around dogs as she knew... (more)"

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6. Rebecca Verified Enhanced Background CheckRover 101

Certified Rover walker!

Lower West Side, Chicago, IL, 60608

Drop-In Visits, Dog Walking

"Rebecca was super nice and Posey loved her! (more)"

7. Ariel Verified Background Check

Caretaker for your furry friend(s)!

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

"Ariel is wonderful with my dog! I have a 70 pound pit mix that likes to pull and, while she looks tiny, she manages to control and hold onto Kobe quite easil... (more)"

8. TIANJIAO Verified Background Check

Furry Fun with Ariel

Loop, CHICAGO, IL, 60605

House Sitting, Drop-In Visits

"This is the 2nd time I have Tianjiao take care of my kitten. The kitten got an ear infection right before I left. Tianjiao took good care of her in my absenc... (more)"

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9. Haley Verified Enhanced Background Check

Animal Pro Works from Home ❤️Pets

Bridgeport, CHICAGO, IL, 60608

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

"My husband and I were headed out of town on vacation and Haley was there for us to take care of our doggos and fishys (our pack). She did a wonderful job car... (more)"

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10. Lilia Verified Background Check

Experienced dog lover!

Hyde Park, Chicago, IL, 60615

Drop-In Visits, Dog Walking

"Lilia was great!! She took the cutest photos of my cat while I was out of town and took the time to play with her :’) great communication on her end. (more)"

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11. Cassidy Verified Background Check

I care for your pets as my own

Hyde Park, Chicago, IL, 60615

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

"Cassidy is a very responsible, attentive, and loving dog caregiver! She grew up with dogs and was their main caregiver - walking, feeding, playing, and taki... (more)"

12. Britney Verified Background Check

I love animals and they love me!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

"Thanks Britney! I’ll always look you up & recommend you to friends for pet sitting! (more)"

13. Alicia Verified Background Check

Understanding pet’s needs

Washington Park, Chicago, IL, 60637

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

"Alicia was great! Our dog is very high energy and is a bit difficult to walk but Alicia handled him great! Would definitely book with her again! (more)"

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14. Cameron Verified Enhanced Background Check

Your Pet’s Favorite Auntie

Near South Side, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Cameron helped us out on really short notice. She was helpful and communicative. I’d definitely (more)"

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15. Monica & Calvin Verified Enhanced Background Check

Dog loving couple in the South Loop

Near South Side, Chicago, IL, 60616

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

About: Hi! My husband and I are dog lovers who live in a condo in the South Loop. We recently lost our dog to cancer and are not ready to have another pu... (more)

16. Arielle Verified Background Check

Student who needs a dog in her life

Hyde Park, Chicago, IL, 60615

Drop-In Visits, Dog Walking

"Arielle was friendly, punctual and communicative during her drop in visits with my cat. She provided lots of updates and pictures while I was gone for a long... (more)"

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17. Madeleine Verified Background Check

I'll love ur dog while you're away!

Kenwood, Chicago, IL, 60615

Dog Boarding, Drop-In Visits, Dog Walking

"Maddie took care of my dog for five days while I was gone on a business trip and I can't say enough about my experience! Maddie constantly sent me pictures o... (more)"

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18. Michael Verified Enhanced Background Check

Big dogs to small I care for all

Near South Side, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Mike is the best dog parent I know. He is so loving and would do anything for his dog. Dogs aside, Mike is also great with people, he is very responsive an... (more)"

19. Eva Verified Background Check

Lifetime Dog Lover & Future Vet!

Kenwood, Chicago, IL, 60515

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

"Eva has a deep passion for dogs, and it is shown in her actions and behavior. Eva has been caring for my dog for three years, and she has such a great relati... (more)"

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20. Cassidy Verified Enhanced Background Check

I'll treat your fur baby as my own.

Douglas, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Cassidy is an excellent and caring pet sitter. She really made my vacation more enjoyable and stress-free knowing that my cat was being taken care of by a de... (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: