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.

1. Theresa

Dog trainer in training

Bridgeport, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

About: I have been around dogs my entire life so I know all of the tricks that they love to pull. Not only have I had dogs my whole life, I am currently p... (more)

2. Laura

Reliable, Caring, and Fun Sitter!

West Town, Chicago, IL, 60642

House Sitting, Drop-In Visits, Dog Walking

"Laura has done such a wonderful job at taking care of my dog, Blue. When Blue had a painful UTI she voluntarily took Blue out for a walk every few hours to h... (more)"

3. Megan

Dog Walker Looking for Clients!!

Loop, chicago, IL, 60605

Drop-In Visits, Dog Walking

7 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)"

4. 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)

5. 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)"

6. 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)

7. 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)"

8. 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)"

9. 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)"

10. 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)"

11. 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)"

12. Cherise

Furever Friends Pet Sitting

Near North Side, Chicago, IL, 60610

Drop-In Visits, House Sitting, Dog Walking

2 repeat clients

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

13. 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)"

14. 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)"

15. 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)"

16. 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)"

17. 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)

18. Alexis

Law Student and Dog Lover

Loop, Chicago, IL, 60605

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

9 repeat clients

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

19. 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)"

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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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: