Pet Setting & Drop Ins In Near South Side 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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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. 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)

Confirmed Holiday Availability
3. MP

Cat and dog lover with experience!

Near North Side, Chicago, IL, 60610

House Sitting, Drop-In Visits, Dog Walking

9 repeat clients

"I cannot thank you enough for taking such great care of my furbabies while I was out of town. All of your check-ins and photos eased my mind with being away.... (more)"

4. Megan

Dog Walker Looking for Clients!!

Loop, chicago, IL, 60605

Drop-In Visits, Dog Walking

5 repeat clients

"Megan did a great job with my cat Helice when I was out of town for one week. She checked in every day by texting me and sending me photos. When I came back ... (more)"

5. 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)"

6. 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 New Years Availability
7. Cherise

Furever Friends Pet Sitting

Near North Side, Chicago, IL, 60610

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Perfect pet-sitter! We highly recommend her. (more)"

8. Philip

Loving and Reliable

Near North Side, Chicago, IL, 60610

House Sitting, Drop-In Visits, Dog Walking

"I am happy to recommend Philip M. as a responsible, caring and conscientious dog sitter. My husband and I are Standard Poodle breeders and give great consid... (more)"

9. 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
10. 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)"

11. 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)"

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 is an amazing dog momma to her boyfriend's dog, Shank. By the way I have witnessed her around Shank and other pups I can say that your dog will be i... (more)"

13. 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
14. Netiya

Caring for others is my passion.

Bridgeport, Chicago, IL, 60609

House Sitting, 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)"

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)"

16. Bernadine

Professional & Caring Dog Sitter

Near North Side, Chicago , IL, 60611

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

About: Hello! My name is Bernadine and I love dogs!! I have always loved animals and grew up with both cats and dogs. I have over 15 years of caring for a... (more)

17. Kellin

Responsible, caring, lover of dogs!

Near North Side, Chicago, IL, 60654

House Sitting, Drop-In Visits, Dog Walking

"Kellin did a great job taking care of our pup for the night and sent us picture updates on his walk. Thanks again! (more)"

Confirmed Holiday Availability
18. Alexis

Law Student and Dog Lover

Loop, Chicago, IL, 60605

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

2 repeat clients

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

19. Rory

I love and appreciate all pups

Loop, CHICAGO, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Rory was great! She was able to stop in at 3am on two nights. (more)"

20. 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)"

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Learn About Premier

Dog owners in Near South Side, Chicago, IL love booking pet sitting with sitters on Rover.com. Over 7,915 pet owners have reviewed pet sitters in Chicago, giving them an average rating of 4.9/5 stars. Booking pet sitting can be super affordable, no matter where you live. Trust us, we think you'll be pleasantly surprised. Curious what it might cost to book pet sitting with Rover? Check out our average pet sitting rates to get an idea before reaching out and starting a conversation with a pet sitter near you in Near South Side, Chicago.

Rover.com is the simple, savvy way to find and book Near South Side, Chicago drop in pet sitting. It's easy to find the perfect pet sitter. Many sitters have offered pet sitting on Rover for years, and 95% of reviewed stays have received a perfect five-star rating. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Pet sitters on Rover have the option to complete a free background check, which you can see from their background check badge. Pet sitters are booked on Rover every minute of every day, and 92% of the population lives within a short drive of one of the more than 65,000 sitters who've listed their services on Rover, so you're sure to find the perfect pet sitter in Near South Side, Chicago . When you book with one of our trusted pet sitters on Rover you get peace of mind that your home and pets are in loving hands.

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 Near South Side, Chicago, 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: