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.

1. Tina

Loving Personal Care Assistant

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

7 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)"

2. Sarah

Life is more fun with a Dog!

Near South Side, Chicago, IL, 60616

Dog Boarding, Drop-In Visits

"I have known Sarah for over 10 years as a friend as well as a coworker. Sarah is extremely responsible and reliable. She is very organized and you can always... (more)"

3. Karolina

Karo the Dog Whispererâ„¢

South Loop, CHICAGO, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

12 repeat clients

"Karolina has sat and done walks for me 3 times. She is very responsive and sends followup messages to let me know how things are going. Will definitely wor... (more)"

4. Charlotte

I'll treat your pet as family!

McKinley Park, Chicago, IL, 60609

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

"Charlotte is an incredibly-knowledgeable dog-lover. She works in a veterinary clinic and knows a lot about dog breeds, temperaments, dietary needs, and so mu... (more)"

5. Maya

Streeterville Sitting

Near North Side, Chicago, IL, 60611

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

"Maya is fun-loving and energetic, with a huge passion for animals and animal welfare - especially dogs! She has always expressed wanting to get involved in a... (more)"

6. Natalie

Loop Living and Pup Loving!

Loop, Chicago, IL, 60607

House Sitting, Drop-In Visits, Dog Walking

"This is our first experience with a pet sitter service and my dog, Sophie, has never had anyone come in prior. WE are so thrilled with Natalie and Sophie ju... (more)"

7. Ashley

Flexible schedule; long walks

Near North Side, Chicago, IL, 60654

Drop-In Visits, Dog Walking

1 repeat client

"Ashley was absolutely wonderful! She was very thorough in describing her visits with my dog & I almost felt like I was home with them. I returned home from m... (more)"

8. Emily

I cry if I see a dog anywhere I am

Loop, Chicago, IL, 60605

Drop-In Visits, Dog Walking

"Emily has dog sat for me and my friends pets in the past . She has always showed compassion for my dogs and has always been reliable. I also know she has ... (more)"

9. Adriana

Outdoor enthusiast &avid dog lover!

Lower West Side, Chicago, IL, 60608

Dog Boarding, 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)"

10. River

Roosevelt student loves your dog!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

About: I have had a dog ( Pomeranian/Yorkie mix) for 5+ years. He's only 8 lbs and one of the sweetest dogs ever. Max is super friendly and he loves to pl... (more)

11. Haley

Young Professional Works from Home

Bridgeport, CHICAGO, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

"Haley has been wonderful with our senior dog. We hired Haley when we found out Peanut has cancer and only a few months left with us. She needs to be watched ... (more)"

12. Kate

I will exercise with your dog!!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

"Kate is perfect when it comes to taking care of pets! She also knows how to make someone's pet feel special. She's the right person to take care of people's ... (more)"

13. 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)"

14. 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)"

15. LeAnna

10+ years of Professional Pet Care!

Hyde Park, Chicago, IL, 60615

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

2 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)"

16. Crystal

Loves all animals

Bridgeport, chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Our pups love Crystal and I can't imagine a better person to be part of our dog team. So grateful Crystal was able to help. (more)"

17. Netiya

Caring for others is my passion.

Bridgeport, Chicago, IL, 60608

Drop-In Visits, Dog Walking

11 repeat clients

"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)"

18. Brittany

Force-Free and Fun!

Bridgeport, Chicago, IL, 60608

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

18 repeat clients

"Brittany is a very professional and patient sitter. We have a very complicated issue between two cats, they don't get along very well with each other, but Br... (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 great with a little doggie who is mostly afraid of people. Little Jax warmed up to her and she took great care of him. 5 Paws for Moesha (more)"

20. Katie

Pup-loving college student

Douglas, Chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

About: I've had pets all my life - dogs, cats, gerbils, snakes, you name it! I love animals and would take care of your dog as if it were my own. I love d... (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: