Pet Sitting & 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.

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1. Nautica Verified Background Check

Extra caring pet lover!

Lower West Side, Chicago, IL, 60616

Drop-In Visits, Doggy Day Care, Dog Walking

"Nautica is the best! Very communicative and great with our two cats. (more)"

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2. Rachel Verified Enhanced Background Check

all dogs are good dogs

Near West Side, Chicago, IL, 60607

House Sitting, Drop-In Visits, Dog Walking

"Rachel was very thorough with her updates and went above and beyond! She did drop in visits for our cat and was the best sitter we’ve had on Rover! (more)"

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3. Ana Carolina Verified Enhanced Background CheckRover 101

I take care of your buddy as my own

Near North Side, Chicago, IL, 60654

Drop-In Visits, Dog Walking

"Ana is a real pet lover and animal safety supporter. She cares a lot of properly caring about cats and dogs, creating real bonds with pets and treating them ... (more)"

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4. Larkin Verified Background Check

Flexible Furbaby Walker

Loop, Chicago, IL, 60603

Drop-In Visits, Dog Walking

"Imagine, full party of 150 people, drinks are flying, conversation is flowing, and where is Larkin? In the corner trynna pet that dawg! Hire her. Solid 10/10... (more)"

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5. Darcy Verified Enhanced Background Check

Ace Ventura for pets 🐶😻

Loop, Chicago, IL, 60605

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

"Darcy was great! She was very communicative, shared many pictures and details of her check on my kitty. She even cleaned up an accident she had - really went... (more)"

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6. Victoria Verified Enhanced Background Check

Run 10 miles? Check. Cuddling?Check

Loop, Chicago, IL, 60601

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

"Victoria did a wonderful job with my cat! Kept me up to date on her plans the day of and well informed once she got there. Will book her again! (more)"

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7. Annie Verified Enhanced Background CheckRover 101

Your 1st kitty/doggy visit FREE ✔

Near South Side, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

"This was my first time using Rover to take care of my cat. I was going to be going out of town for 11 days and with that, I was hesitant with someone I didn... (more)"

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8. Vanessa Verified Enhanced Background Check

Walking with love

Loop, Chicago, IL, 60605

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

About: I just moved to Chicago in December so I figured this would be a great way to get out and explore the city. I've had dogs my whole life when I live... (more)

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9. Michael Verified Enhanced Background CheckRover 101

Always at Home & Right by Dog Park!

Near South Side, Chicago, IL, 60616

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

"Michael is an honest, responsible, and trustworthy person. Anytime I need someone to watch my two dogs, I always check to see if Michael is available. He is ... (more)"

10. TIANJIAO Verified Background Check

Furry Fun with Ariel

Loop, CHICAGO, IL, 60605

House Sitting, Drop-In Visits

"This is the 2nd time I have Tianjiao take care of my kitten. The kitten got an ear infection right before I left. Tianjiao took good care of her in my absenc... (more)"

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11. Tricia Verified Background Check

medical student who loves animals!

Near South Side, Chicago, IL, 60605

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

About: Hi! I'm a medical student at Feinberg School of Medicine in Chicago. I am currently in my pre-clinical years, which means I have a lot of flexibili... (more)

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12. Michael Verified Enhanced Background Check

I treat your pet like it’s mine.

Near South Side, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Very impressed with the walk/drop in visit. Updated me with photos throughout the visit. Michael really cares for your puppies overall being. (more)"

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13. Megan Verified Background Check

I am very passionate about animals!

Loop, Chicago, IL, 60605

Drop-In Visits, Dog Walking

"Megan watched our golden doodle puppy for two weeks and did an amazing job. She is a gem! She followed feeding and potty training instructions to a tee. I de... (more)"

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14. Nikki Verified Enhanced Background Check

Pet LOVER; making your day easier!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

"Nikki is such a find! She is very likable person, very smily, very pleasant, good with dogs 🐕 She visited our fur baby a few times already and the first time... (more)"

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15. Anna Verified Background Check

Loving & Caring Professional

Near South Side, Chicago, IL, 60605

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

About: I love long walks, I think it’s necessary for a dog to exercise a little bit and enjoy some fresh air. Due to my flexible schedule, I can spend mor... (more)

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16. Rachael Verified Background CheckRover 101

Dog lover w/ fenced yard

Loop, Chicago, IL, 60605

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

"Rachael has a gift for connecting with our canine friends. She has a way of understanding and caring for them that is truly remarkable. I've known Rachael fo... (more)"

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17. Lisa Verified Enhanced Background CheckRover 101

Home full-time - lives by dog park

Near South Side, Chicago, IL, 60616

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

"It is a real pleasure that I recommend Ms. Hui for a position as a dog caregiver. she is enormously responsible, hardworking and caring dog sitter. Our dog h... (more)"

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18. Lily Verified Background Check

Eager to watch new furry friends!

Near South Side, Chicago, IL, 60616

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

About: I get to work from home so I have a lot of flexibility and can give lots of attention! I live in a quiet neighborhood with one of the most popular ... (more)

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19. Monica & Calvin Verified Enhanced Background Check

Dog loving couple in the South Loop

Near South Side, Chicago, IL, 60616

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

"Calvin was fantastic - really helped me out last minute, very accommodating, communication was speedy, and the best part was that he sent videos and tons of ... (more)"

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20. Chloe Verified Background Check

I'm an animal person all around!

Near South Side, Chicago, IL, 60616

Drop-In Visits, Doggy Day Care, Dog Walking

About: I often would pet sit for my friends, their dogs, cats and even hamsters sometimes, however my parents never allowed me to have a pet other than a ... (more)

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: