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. Cindy

South Loop doggie disneyland

Near South Side, Chicago, IL, 60605

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

"Cindy did a wonderful job taking care of my Jack Russell Terrier! She listened cautiously to my concerns of leaving my dog, Buster, with a stranger. I defin... (more)"

2. Margarita

I love pups of all ages and sizes!

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

"Margarita is one of the most responsible people I know. She is very patient, reliable, and is one of the nicest people you will have the pleasure of working ... (more)"

3. Karolina

Karo the Dog Whisperer™

South Loop, CHICAGO, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

13 repeat clients

"Karolina has sat and done walks for me 3 times. She is very responsive and sends followup messages to let me know how things are going. Will definitely wor... (more)"

4. Enoch

Dogs/cats/other pets welcomed!

Bridgeport, Chicago, IL, 60608

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

17 repeat clients

"Enoch is a very professional cat sitter. He knows a lot about how to communicate and play with cats. I feel very comfortable to leave my cats with him. He fe... (more)"

5. Somer

Home full-time - live next to a par

Loop, Chicago, IL, 60605

Dog Boarding, Drop-In Visits, Doggy Day Care

About: I am happily married to my best friend. We recently moved to Chicago from Southern California since my husband was transfered for work. We currentl... (more)

6. Megan

Petsitter looking for new clients!

Loop, chicago, IL, 60605

Drop-In Visits, Dog Walking

29 repeat clients

"Megan did a great job and really gave us peace of mind for going out of town. We loved the photos we received from her visits and the cats seemed to really l... (more)"

7. Alexandra

Reliable & Loving Sitter

Near South Side, Chicago, IL, 60616

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

2 repeat clients

"Alex took great care of my cat when I was traveling! She sent pics and kept me updated during my trip. I would recommend Alex to anyone who needs a responsib... (more)"

8. Jory

Dog lover on the go!

Near North Side, Chicago, IL, 60654

House Sitting, Drop-In Visits

5 repeat clients

"Jory is a caring and wonderful friend to our beloved pet. He takes the time to know our dog and care for her while we are away. I would recommend Jory for ... (more)"

9. Jess

College student. Major dog lover!!

Loop, Chicago, IL, 60604

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

"Jess is one of the best people anyone could have take care of their dog. She loves dogs so much and treats them better than she would herself!! Her fun and... (more)"

10. Elizabeth

Owned & worked w/ dogs all my life!

Bridgeport, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

"Very pleased with the compassion, care and attentiveness that Liz has shown for my Bella. Liz was recommended by another great Rover walker. Due to my hectic... (more)"

11. Kalli

I'll love your dog like my own!

Lower West Side, Chicago, IL, 60608

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

About: I have had dogs since I was little. My family has always had two German Shepherds at a time. I love the joy a dog brings to a household! After movi... (more)

Confirmed President's Day Availability
12. Andrew

Can't wait to meet your Pup!

Lower West Side, Chicago, IL, 60608

House Sitting, Drop-In Visits, Dog Walking

"Andrew has been watching and walking my dog for the past year. My dog requires a lot of one on one attention and Andrew always provides that to her. She also... (more)"

13. Tina

Loving Personal Care Assistant

Bridgeport, Chicago, IL, 60616

House Sitting, Drop-In Visits, Dog Walking

8 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)"

14. Collin

Gentle Soul, Love Animals, Reliable

Near South Side, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

7 repeat clients

"Collin is always so wonderful with Scrappy and gives him tons of attention and affection. He always looks so happy in his pictures on the Rover Card. (more)"

Confirmed President's Day Availability
15. Ivana

College student who loves dogs!

Loop, Chicago, IL, 60601

House Sitting, Drop-In Visits, Dog Walking

"Ivana is a super awesome human being and as nice as she is to other human beings, she’s even nicer to dogs! I would definitely recommend hiring her as a dog ... (more)"

Confirmed President's Day Availability
16. Amber

MBA student loves dogs!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients
No Reviews Yet

About: I am a dog-loving current MBA student at the University of Chicago with free time between classes. I grew up with medium sized (35-50 pounds) dogs ... (more)

17. Josh

Any dog out there is family to me.

Douglas, Chicago, IL, 60653

House Sitting, Drop-In Visits, Dog Walking

"He has taken great care for our princess and even had time to walk her more when she needed to! Knows how to love a pet and was very patient with her. Couldn... (more)"

18. Anthony

Dogs deserve the best... that's me!

Loop, Chicago, IL, 60605

Drop-In Visits, Dog Walking

"Anthony has always been a dog lover. He cared for his dog Santana until the day he died. Santana was prone to ear infections and Anthony learned how to lovin... (more)"

Confirmed President's Day Availability
19. Jameel

Your pup's pal, no matter the size!

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

"Jameel loves every dog, whether it is his two dogs at home, or any dog on the street. His gentle and loving nature, combined with his commitment and resolute... (more)"

20. Emily

~ Prices Vary, Name your Price ~

Loop, Chicago, IL, 60605

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Emily watched my dogs many times while I was away on business trips and I always feel bad leaving them but she always cheers them up. She also has really aff... (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: