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.

1. Hillary

Experienced Dogsitter in West Town

West Town, Chicago, IL, 60622

Dog Boarding, House Sitting, Drop-In Visits

About: Hello! My name is Hillary and I've been dogsitting for about three years. I have experience dogsitting in a city environment, from when I lived in ... (more)

2. Annina

* Outdoor Loving and Active *

North Lawndale, Chicago, IL, 60623

Drop-In Visits, Dog Walking

8 repeat clients

"Annina took very good care of our cats while we were away for a week. From the moment of our meet and greet, we were delighted to have her as our sitter. S... (more)"

Available this weekend
3. Kendra

Dog lover trapped as Consultant

Lincoln Park, CHICAGO, IL, 60614

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

About: I am a management consultant who has a flexible travel schedule for now and am available 7 days a week through the 29th of January. If you are ... (more)

4. Ashleigh

Dog loving student in Chi

Near South Side, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Ashleigh was great! She came by to meet Boba and get the leys to our apartment before hand and checked on Boba at the times she said. She also sent a bunch o... (more)"

5. Serena

Loving Student in Loop

Loop, Chicago, IL, 60604

House Sitting, Drop-In Visits, Dog Walking

"Serena is an amazing person and a huge dog lover. If our looking for a loving and caring dog walk or sitter, Serena is the perfect match for you. So much ene... (more)"

6. Dominique

Let me be your Fairy Dog Mother!

Near West Side, Chicago, IL, 60612

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

"Dominique is one of my best friends and the greatest Aunt Tommy golden retriever, Bomber. She came with me to meet him and take him home on day one, and ... (more)"

7. Dalit

I already love your dog :)

Near North Side, Chicago, IL, 60610

Drop-In Visits, Dog Walking

1 repeat client

"My dog Doodles had a great time with Dalit, think they explored more of Chicago than I have yet! Very friendly and quick to respond, plus received plenty of ... (more)"

8. 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)"

9. Hailey

I catch the eyes of your dogs!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

3 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)"

10. 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)"

11. Rebekah

Dependable, Prompt, & Caring.

Near North Side, Chicago, IL, 60610

House Sitting, Drop-In Visits, Dog Walking

"Rebekah's love for dogs show in the way she handles & interacts with them. Entrust your pets care to Rebekah & you won't be disappointed! (more)"

12. 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)"

13. Maddie

I absolutely love all animals!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"Maddie was great! She sent me Rover cards with pictures of Coco. When we returned home Coco was very happy! We definitely recommend Maddie and we'll be using... (more)"

14. Moesha

College student that loves Dogs!

Douglas, chicago, IL, 60616

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

15. Sarah

Will show your pup so much love!!!!

Bridgeport, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Sarah is a loving, enthusiastic dog caregiver who I have trusted with my beloved French Bulldog, Pablo several times in the past. She is very responsible an... (more)"

16. 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)

17. Alexis

Law Student and Dog Lover

Loop, Chicago, IL, 60605

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

7 repeat clients

"Alexis was great and she always kept us updated! (more)"

18. Madison

Pup Loving Student

Loop, Mount Pleasant, SC, 29466

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Madison was great! Very communicative and sent me photo updates of my cat each day which I appreciated immensely. I would use her services again! (more)"

19. Josh

NCAA STUDENT ATHLETE. 3.5 student.

Lower West Side, Chicago, IL, 60608

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

"This was my first time using Rover, and Josh was very accommodating throughout the whole process. I highly recommend him to anyone looking for a sitter. (more)"

20. Sam

Improving lives, one dog at a time

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

3 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)"

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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.

Want to be added to this list of sitters in Chicago? Become a pet sitter or dog walker on Rover.

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.