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. Cosette

Forever dog-lover

Bridgeport, Chicago, IL, 60608

Drop-In Visits, Doggy Day Care, Dog Walking

About: Hi there! I am a careful and attentive dog (and kid) sitter, with lots of love to give! I have owned and cared for dogs since a child and currently... (more)

2. Isabella

Summers off and energetic

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Isabella is the true definition of an animal lover. She truly appreciates animals, unlike anyone I have ever met. Whenever she sees a dog, she rushes over to... (more)"

Available this weekend
3. Adriana

Outdoor enthusiast &avid dog lover!

Lower West Side, Chicago, IL, 60608

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

"Adriana is very efficient, caring and will take care of your pet as her own! Her flexibility and attention to detail is what makes her stand out, not to ment... (more)"

4. Karolina

Karo the Dog Whispererâ„¢

South Loop, CHICAGO, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"Excellent host! And so thankful for the availability on short notice! (more)"

5. KC

Loving Pet Sitter/Nursing Student

Near West Side, Chicago, IL, 60607

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"KC was great and sent pictures each day. I really appreciated her amazing communication before, during, and after the pet sitting! (more)"

6. 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)"

7. Robert

All furry friends welcome!

Loop, Chicago , IL, 60601

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

13 repeat clients

"Robert was amazing, and at such short notice. Pudding was walked, fed and taken care of when I had to be out of town for a quick meeting at the last minute. ... (more)"

8. 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)

9. Maia

Cubby Loves Puppies

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"To say your pet is in good hands with Maia is an understatement. She is an extremely capable and reliable pet sitter. She's caring and very experienced with ... (more)"

10. Breana

Dogs are my favorite people.

Hyde Park, Chicago, IL, 60615

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

1 repeat client

About: Hello everyone! My name is Breana :). I am currently obtaining my Master's in Speech-Language Pathology. I am reliable, responsible and an animal l... (more)

11. Simone

Professional Pup Lover!

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Simone is a wonderful person and caregiver. Whenever I have Simone petsit for my dog & cats, I am always kept updated on how my babies are doing, and feel 10... (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. 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)"

14. Netiya

Caring for others is my passion.

Bridgeport, Chicago, IL, 60609

House Sitting, Drop-In Visits, Dog Walking

8 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)"

15. Emma

PhD in dog walking & cat cuddling

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

8 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)"

16. Rebba

Dog Lover in Hyde Park

Hyde Park, Chicago, IL, 60615

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

2 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)"

Available this weekend
17. Anne

Grad Student Ready to Love Your Pup

Hyde Park, Chicago, IL, 60615

Drop-In Visits, Dog Walking

"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)"

18. Eleanor

Because it really is my pleasure :)

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Eleanor cares for all living things with unparalleled empathy. She is kind to and patient with animals. My roommate's cats hate me but they love Eleanor. (more)"

19. Chornodub

home full time and love animals

Douglas, Chicago, IL, 60616

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

About: Hello, my name is Tia. Why I love animals? 1. They are soooo cute!!! 2. They love you as much as you love them. 3. They are a friend. 4. Anim... (more)

20. 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)"

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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: