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. Karolina

Karo the Dog Whispererâ„¢

South Loop, CHICAGO, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

10 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)"

2. 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)"

3. Mindy

5-Star Care Custom-Tailored Stays

Douglas, Chicago, IL, 60616

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

About: My 1890's rowhouse with 3,300 sq. ft. and fenced front and back yards will be a perfect home to assure a safe and enjoyable stay for your four-legg... (more)

4. Caraline

Experienced & Certified Pet Sitter

Loop, Chicago, IL, 60606

Drop-In Visits, Dog Walking

3 repeat clients

"Caraline was great. She took great care of my kitties. She played with them and even brushed them. Now I can go on trips knowing my kitties are well take... (more)"

5. Bri

I like dogs more than people.

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

"Brianna is amazing with others especially with animals very caring and wants the best for the people she cares about . I've enjoyed working with her over th... (more)"

6. Robert

All furry friends welcome!

Loop, Chicago, IL, 60601

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

21 repeat clients

"Robert was fantastic! I could tell Duke had so much fun with him during his drop in visits. Robert is so knowledgeable of dogs especially our breed, a French... (more)"

7. Phoebe

Lots of availability - Lots of love

Bridgeport, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Phoebe took excellent care of our Pomeranian while we spent our annual week at Disney World. It seemed like she and Moxie really bonded - we felt like we lef... (more)"

8. Miranda

Needing a lovely walking companion

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

About: Hello! I am 21 years old, I live in Chicago and have for 4 years now, and I have been raised around large and small dogs my whole life! I currently... (more)

9. Adriana

Outdoor enthusiast &avid dog lover!

Lower West Side, Chicago, IL, 60608

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

1 repeat client

"Adriana is a wonderful petsitter. Always kind, caring, and puncutial when taking care of our little puppy Valentine. She is super nuturing and always has his... (more)"

10. Anne

Grad Student Ready to Love Your Pup

Hyde Park, Chicago, IL, 60615

Drop-In Visits, Dog Walking

2 repeat clients

"Anne texted me each time she was there, even sending updates when our dog had an upset stomach. Thanks Anne for a great weekend of care for our dog!! (more)"

Available this weekend
11. 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)"

12. 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)"

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. 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)"

15. Collin

Gentle Soul, Love Animals, Reliable

Near South Side, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"Collin is always so wonderful with Scrappy and gives him tons of attention and affection. He always looks so happy in his pictures on the Rover Card. (more)"

16. Audrey

Dogs are my life!

Bridgeport, Chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

"Audrey is great with animals. She is very caring and experienced with animals. I've seen Audrey take wonderful care of her pet cat. She has grown up aroun... (more)"

17. Brooke

High energy dog expert!

Bridgeport, Chicago, IL, 60609

Drop-In Visits, Dog Walking

"Brooke is awesome and genuinely loves to care for animals. She has always been a huge animal lover and puts their needs and desires above her own. I would tr... (more)"

18. Netiya

Caring for others is my passion.

Bridgeport, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

9 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)"

19. Rebba

Dog Lover in Hyde Park

Hyde Park, Chicago, IL, 60615

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

4 repeat clients

"I was traveling out of town for two weeks in January and needed a pet sitter. Rebba was an amazing dog sitter to my beloved Mr. Jinx. She sent me daily photo... (more)"

20. Billie

Experience, love and care

Grand Boulevard, Chicago , IL, 60653

House Sitting, Drop-In Visits, Dog Walking

About: I am a client care coordinator at a well established veterinary practice. In addition to working with dogs and cats on a daily basis, I have had pe... (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.

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