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. Lily

Very active dog lover!

Lincoln Park, Chicago, IL, 60614

House Sitting, Drop-In Visits, Dog Walking

"Lily would be an awesome pet sitter! First of all she loves animals, especially dogs and cats, and loves to play, snuggle, walk, and love them! Lily is ext... (more)"

Available this weekend
2. Megan

Dog Walker Looking for Clients!!

Loop, chicago, IL, 60605

Drop-In Visits, Dog Walking

8 repeat clients

"Megan was amazing! I had to book a few same-week visits, and we weren't able to squeeze in a meet & greet beforehand. I wrote out detailed instructions, and ... (more)"

3. Kim

Dog (& Cats) our 4-Legged Family

Lincoln Park, Chicago, IL, 60614

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

About: I'm an animal lover! Since the day I was born (29 years ago) I've always had at least 2 cats and a dog. Currently I have 4 cats (three are 6 years ... (more)

4. Ashleigh

Dog loving student in Chi

Near South Side, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

6 repeat clients

"Our dog Babs had emergency surgery over the Christmas holiday, and we needed someone last minute to look after her while at work and give her some medicine d... (more)"

5. 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)"

6. 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)"

7. Lena

Loving college student/trainer

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

About: While my main focus is finishing my degree in marketing, I would love to fit in my love for animals as well! You can be assured that your dog will ... (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. Emma

PhD in dog walking & cat cuddling

Hyde Park, Chicago, IL, 60615

House Sitting, Drop-In Visits, Dog Walking

7 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)"

10. Cherise

Furever Friends Pet Sitting

Near North Side, Chicago, IL, 60610

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Very positive experience with chewy (more)"

11. Penelope

Loving dogs more than anything

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

10 repeat clients

"I had Penelope come over a few times a day while I was out of town to make sure my 2 dogs were doing well. She made sure they were fed, loved and taken care ... (more)"

12. 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 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. Jac

Loving and Experienced Pet Sitter

Bridgeport, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Jac looked after my sweet corgi, Oliver, while I went away for a weekend. She took amazing care of him! She even sent little pictures of them having fun toge... (more)"

14. Vanessa

Fun caring dog lover.

Near North Side, Chicago, IL, 60654

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

6 repeat clients

"Vanessa was awesome. We will definitely be using her again. She and my dog got along really well and he seemed very happy when we came back from our trip. (more)"

15. Catherine

Patient & trustworthy animal lover!

Near West Side, Chicago, IL, 60607

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Catherine has been an animal lover since I've known her. She volunteered at a dog rescue shelter while away at college and continues to volunteer with a Chic... (more)"

16. 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)"

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. 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)"

19. Silvia

Vegetarian/Animal lover/Writer

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

About: Hello! My name is silvia. I was an animal caregiver at PAWS Chicago for 2 years. PAWS is a nationally known no-kill shelter with a hospital located... (more)

Available this weekend
20. Collin

Gentle Soul, Love Animals, Reliable

Near South Side, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Collin S. has loved dogs since he was a young boy. I have observed the close bond he has with his dog Joey, for over a decade. Collin also enjoys the neigh... (more)"

Experience exceptional service and a personalized match

From start to finish, we'll handle all the details for you.

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: