Drop-In Visits in 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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Available this weekend
1. Mark

Bark Voyage!

Lincoln Park, Chicago, IL, 60614

House Sitting, Drop-In Visits

About: Being away from you is stressful for your dog, so why make it even more stressful by making your furry friend leave home? I am a 26 year old Chic... (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. Jordan

Pro walker seeking new pup clients

West Town, Chicago, IL, 60647

House Sitting, Drop-In Visits, Dog Walking

About: Hello! I'm Jordan. I have a year of experience walking dogs with an agency, managing a regular daily route of 10+ dogs. I've also dog and cat-sa... (more)

4. 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)

5. Annina

* Outdoor Loving and Active *

North Lawndale, Chicago, IL, 60623

Drop-In Visits, Dog Walking

3 repeat clients

"Annina was a fantastic sitter! She was always prompt in responding and kept me updated every single time she dropped in to check on my cats. I felt totally c... (more)"

6. Ashley

Dogs are are more than a bestfriend

Lincoln Park, Chicago, IL, 60614

House Sitting, Drop-In Visits, Dog Walking

About: Hi , my name is Ashley and I am a new resident to the city. I work a corporate job Monday-Friday but have lots of free time before/after work, and ... (more)

7. 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)"

8. 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 Holiday Availability
9. MP

?? walking and drop in visits!

Near North Side, Chicago, IL, 60610

House Sitting, Drop-In Visits, Dog Walking

8 repeat clients

"MP was wonderful and very cooperative. Two of my dogs are elderly and one somewhat neurotic but they were all in great health and happy spirits when I retur... (more)"

Confirmed New Years Availability
10. 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)"

11. Shana

Loving. Active. Responsible.

Loop, Chicago, IL, 60605

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

1 repeat client

"Shana was great! Very communicative and responsible in taking care of my elder cat, Phoebe. I would definitely recommend her! (more)"

Confirmed Holiday Availability
12. Moesha

College student that loves Dogs!

Douglas, chicago, IL, 60616

Dog Boarding, House Sitting, Drop-In Visits, 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)"

13. 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)"

14. Tatiana

Graduate student who loves dogs!

Near South Side, Chicago, IL, 60605

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

2 repeat clients

"Tatiana did an excellent job of caring for my dog while I was on vacation. Before I left I wanted to see how she and my pup interacted and she was just fanta... (more)"

15. 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)"

Confirmed Holiday Availability
16. Netiya

Caring for others is my passion.

Bridgeport, Chicago, IL, 60609

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)"

17. 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)"

Confirmed Holiday Availability
18. 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)

19. 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)"

20. Sabrina

Loving life, but loving dogs more!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Sabrina is a very loving, caring, responsible dog caregiver. She took care of our Doberman Max from puppy-hood until his last day on Earth. She also took c... (more)"

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Pet owners love Chicago pet sitters on Rover. 9,532 owners have reviewed sitters in the Chicago, IL metro area, giving them an average rating of 4.9/5.

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Never beg a friend to drop in on your pets while you're on vacation again. With Rover, you can find the perfect pet sitter in seconds. Rover sitters 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 who can provide the care your pet needs, when they need it.