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 Holiday Availability
1. Tina

Loving Personal Care Assistant

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

8 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)"

2. Karolina

Karo the Dog Whispererâ„¢

South Loop, CHICAGO, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

13 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)"

3. Enoch

Dogs/cats/other pets welcomed!

Bridgeport, Chicago, IL, 60608

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

15 repeat clients

"Enoch is a very professional cat sitter. He knows a lot about how to communicate and play with cats. I feel very comfortable to leave my cats with him. He fe... (more)"

4. Britney

I love animals and they love me!

Loop, Chicago, IL, 60605

Drop-In Visits, Dog Walking

1 repeat client

"Britney did an excellent job with Thor. He takes a lot of patience and she had it to give. She was also very good at sending us updates regularly. I highly r... (more)"

5. Adriana

Outdoor enthusiast &avid dog lover!

Lower West Side, Chicago, IL, 60608

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

2 repeat clients

"Adriana did a great job when watching my two dogs last week when I was out of town for work. She was reliable, followed all directions, and was very good wi... (more)"

6. Alexandria

Pup Adventures with Alex

Near South Side, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

14 repeat clients

"Alex was great! She took my reservation at the last minute for Thanksgiving weekend to take care of my cat Bean. She stopped by daily to feed Bean and play w... (more)"

Confirmed Holiday Availability
7. Jessica

Home full time-

Near South Side, Chicago, IL, 60616

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

"Jessica is the best when it comes to reliability and dog care. She has had dogs her whole life and I have never met anyone that loves and cares for dogs and... (more)"

8. Payal

West Town Pet Sitter

McKinley Park, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

20 repeat clients

"Payal was a better dog-sitter than I could have hoped for. It was our first time leaving Zeke alone with a stranger and she was very caring and attentiveness... (more)"

9. LeAnna

13 years of Professional Pet Care!

Hyde Park, Chicago, IL, 60615

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

4 repeat clients

"LeAnna is very professional, and did a great job looking after our little puppy, Isla. She is friendly, fun, and has tons of experience with caring for pets,... (more)"

10. Sara

UIC area dog lover, reliable & fun

Near West Side, Chicago, IL, 60607

Drop-In Visits, Dog Walking

"Not only is Sara a super sweet person she also is great with animals. So much so that she helps me with my own dog, Zeus, all the time. And he is always so h... (more)"

Confirmed Holiday Availability
11. Simone

Professional Pet Lover!

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"From start to finish, Simone did an incredible job looking after our cats! When she came to meet them, she had already read over the information I provided a... (more)"

12. Richa

Full-Time Dog Mom!! :)

Near South Side, Chicago, IL, 60605

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

4 repeat clients

About: Hello!! I am a stay at home dog mom :). In the past year, I have been dog sitting full-time since my husband has been busy with finishing his gradu... (more)

13. Christian

PAWS volunteer,rescuer

McKinley Park, Chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Christian was awesome and extremely accommodating with such short notice! He came to a meet and greet literally the night before we needed him. He was friend... (more)"

14. Vivian

Experienced walker + home full-time

Lower West Side, Chicago, IL, 60608

Drop-In Visits

About: Hi I'm Viv! I work from home as a freelance photographer in the Pilsen area. My schedule is very flexible and I can tend to your dog at any hour... (more)

15. Brenna

I'm PAW-sitive I'm the best match!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Brenna is a very responsible, reliable and trustworthy person. She has cared for many dogs throughout her life, and has been a dog owner since day one. (more)"

16. Nicole

We'll put a Woof over their head!

Near South Side, Chicago, IL, 60616

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

4 repeat clients

About: Why board your pet in a loud, cramped cage at a kennel when you can take them to a nice, comfy home where they can run free? While here, they'll re... (more)

17. Crystal

Loves all animals

Bridgeport, chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

3 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 Holiday Availability
18. Netiya

Caring for others is my passion.

Bridgeport, Chicago, IL, 60608

Drop-In Visits, Dog Walking

13 repeat clients

"Netiya was amazing!!! We had to book a cat sitter last minute and Netiya was both very responsive and flexible! She sent us photos of our cat while we were a... (more)"

19. 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 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)"

20. 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)"

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: