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.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
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Confirmed Holiday Availability
1. Stacy

Only the Best for Your Furry Bffs

Loop, Chicago, IL, 60605

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

About: Hi, I'm a recent college grad living in South Loop with my goldendoodle. My schedule is completely flexible because I work at home most times. I ... (more)

2. Nick

DOGS ARE LIFE

Loop, Chicago, IL, 60607

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

"Nick would be a fantastic and trustworthy dog caregiver. He grew up in house with 2 dogs, so he has experience with dogs. Nick is also straight A responsible... (more)"

3. Kristen

Playdate with Bernadette!

Oakland, Chicago, IL, 60653

Dog Boarding, Drop-In Visits, Dog Walking

About: I specialize in taking care of female dogs. I had an older French Bulldog named Mischue (Polish for teddy bear) who lived to be 15 years old and a... (more)

4. 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)"

5. Hailey

I catch the eyes of your dogs!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"To whom it may concern, Hailey is a very positive and optimistic person. She is caring and very thoughtful and the positive energy she brings makes her a ... (more)"

Confirmed New Years Availability
6. Cherise

Furever Friends Pet Sitting

Near North Side, Chicago, IL, 60610

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Very positive experience with chewy (more)"

Available this weekend
7. 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)"

Confirmed Holiday Availability
8. Alexis

Law Student and Dog Lover

Loop, Chicago, IL, 60605

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

3 repeat clients

"Alexis was great and she always kept us updated! (more)"

Confirmed Holiday Availability
9. Moesha

College student that loves Dogs!

Douglas, chicago, IL, 60616

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

3 repeat clients

"Moesha was very nice when we met for our meet and greet and assured me that our sweet kitty boy would be in great hands! She came to our place in the morning... (more)"

10. Stefani

Dog lover-looking to love your pet

Near North Side, Chicago, IL, 60611

House Sitting, Drop-In Visits, Dog Walking

"Stefani is awesome and did a great job! (more)"

11. Sam

Improving lives, one dog at a time

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

2 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)"

12. Holly

Dog lover 1st, law student 2nd!

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Holly took great care of my cats, Fisher and Bugaloo. I appreciated the daily updates and photos. They had plenty of food and water when I returned home. Hig... (more)"

13. Tina

Loving Personal Care Assistant

Bridgeport, Chicago, IL, 60616

Drop-In Visits, Dog Walking

5 repeat clients

"Tina did a great job taking care of our two cats while we were out of town for a long weekend! She was very responsive to our requests and was readily availa... (more)"

14. Madison

Pup Loving Student

Loop, Mount Pleasant, SC, 29466

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Madison was great! Very communicative and sent me photo updates of my cat each day which I appreciated immensely. I would use her services again! (more)"

Confirmed Holiday Availability
15. Netiya

Caring for others is my passion.

Bridgeport, Chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"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)"

16. Ashleigh

Dog loving student in Chi

Near South Side, Chicago, IL, 60615

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

2 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)"

17. Rory

I love and appreciate all pups

Loop, CHICAGO, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Rory was great! She was able to stop in at 3am on two nights. (more)"

18. 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)"

Confirmed Holiday Availability
19. Brittany

Compassionate and Patient

Bridgeport, Chicago, IL, 60608

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

About: I moved to Chicago from Gainesville, FL to get a fresh perspective and a change of pace. I'm an artist who spends most of my time making comics and... (more)

20. LeAnna

10+ years of Professional Pet Care!

Hyde Park, Chicago, IL, 60615

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

"I have known LeAnna for nearly 2 decades and have never known anybody as pleasant, caring and even-tempered when dealing with all kinds of animals, especiall... (more)"

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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: