Pet Sitting & Drop Ins in Kenwood, Chicago

Book a pet sitter to stop by your home a few times a day to feed and play with your dog.

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
One Time
Repeat Weekly
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Sitter Profile Image: Coretta S.
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Sitter Profile Image: Coretta S.
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1. Coretta S.

Star Sitter
Loves to accommodate furry friends
South Shore, Chicago, IL, 60649
3.5 mi. away
Boarding, Drop-In Visits, Dog Walking
5.0 out of 5 stars
58 reviews
21 repeat clients
from
$17
per visit

Coretta is awesome!! She dropped in on my fur babies twice a day while I was away. She sent a detailed summary and photos after each visit. She followed all instructions regarding their feeding and medication, as well as instructions regarding opening/closing the blinds and activating the echo dot each day to give them some background noise. I can be a little overprotective of my kitties, but I was able to enjoy my trip because I felt confident that she was taking care of them!!

Sitter Profile Image: Crystal R.
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Sitter Profile Image: Crystal R.
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2. Crystal R.

Star Sitter
My home is where your pet is.
Chicago, IL, 60653
1.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
96 reviews
40 repeat clients
from
$21
per visit

Crystal was timely and very communicative while watching my cats. I’m so glad to have found her and look forward to scheduling with her in the future.

Sitter Profile Image: Emily N.
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Sitter Profile Image: Emily N.
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3. Emily N.

Star Sitter
Experience with multiple sized dogs
Bridgeport, Chicago, IL, 60616
3.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
117 reviews
36 repeat clients
from
$20
per visit

Emily went above and beyond for my cats. One of my cats had a vomiting incident and Emily went so far as to clean/disinfect the rug and drag it into my room to keep the cats away from the disinfectant on the rug while it dried. The cats also loved her as usual!

Sitter Profile Image: Dominique C.
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Sitter Profile Image: Dominique C.
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4. Dominique C.

Lifelong Dog Lover and Caregiver!
Woodlawn, Chicago, IL, 60637
2.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
7 reviews
4 repeat clients
from
$20
per visit

Dominique is excellent with Lily. She is patient, kind, and playful with her. She really goes the extra mile when working with my Lily. She is always on time and reliable. I highly recommend Dominique.

Sitter Profile Image: Elizabeth D.
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Sitter Profile Image: Elizabeth D.
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5. Elizabeth D.

Does your pet need a new friend?
Douglas, Chicago, IL, 60609
1.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
24 reviews
5 repeat clients
from
$23
per visit

levi you were so amazing!! we looked forward to your updates every day - thank you for taking such great care of cal and santi!! we hate to leave them but it was such a comfort knowing you were around

Sitter Profile Image: Haley B.
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Sitter Profile Image: Haley B.
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6. Haley B.

🐈‍⬛ Cat Whisperer in Hyde Park! 🐈
Hyde Park, Chicago, IL, 60637
1.3 mi. away
Drop-In Visits
5.0 out of 5 stars
14 reviews
3 repeat clients
from
$21
per visit

Haley is amazing! I'm so glad that I found her on Rover. I have the utmost confidence that my two cats will be well-cared for while I am away on vacation or business trips. She really is a life saver. I appreciate that she kept me informed while I was away and her attention to detail is keen. I highly recommend Haley. You should have no hesitation about booking her to care for your pets - except on the days when I need her. :-) Cheers, Haley.

Sitter Profile Image: Juan-Pablo A.
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Sitter Profile Image: Juan-Pablo A.
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7. Juan-Pablo A.

College student and animal lover
Chicago, IL, 60615
1.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
11 reviews
5 repeat clients
from
$16
per visit

Juan-Pablo was so good with Frankie! He really took the time to listen to my requests and make sure Frankie was 100% comfortable with him. She had a great time with Juan-Pablo. Would definitely trust her with him again in the future.

Sitter Profile Image: Katherine B.
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Sitter Profile Image: Katherine B.
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8. Katherine B.

Star Sitter
🐶Who's a good dog? Trick question!
Grand Boulevard, Chicago, IL, 60615
0.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
56 reviews
16 repeat clients
from
$20
per visit

Katherine was great! Came in clutch for a last minute cat sitting request and provided really detailed updates and lots of photos/videos while I was away. I came home to a happy kitty and watered plants.

Sitter Profile Image: Elizabeth H.
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Sitter Profile Image: Elizabeth H.
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9. Elizabeth H.

I already love your dog!
Woodlawn, Chicago, IL, 60637
1.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
12 reviews
5 repeat clients
from
$17
per visit

Elizabeth is the best super responsive and very helpful she took great care of cat and sent me a picture everyday I definitely would recommend her! She even dropped my keys off for me 10/10

Sitter Profile Image: Kayleigh P.
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Sitter Profile Image: Kayleigh P.
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10. Kayleigh P.

Long-time animal lover
Hyde Park, Chicago, IL, 60615
0.5 mi. away
Drop-In Visits
5.0 out of 5 stars
6 reviews
1 repeat client
from
$20
per visit

Kayleigh was very kind and was amazing with our cat! Our cat has accidents sometimes, but she was able to clean them while we were away. We appreciated her playing with our cat and making sure that she was well taken care of! Thank you!!!

Sitter Profile Image: Taylor L.
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Sitter Profile Image: Taylor L.
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11. Taylor L.

Loving Pet Sitter, Cats & Dogs
Kenwood, Chicago, IL, 60615
0.7 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
4 reviews
1 repeat client
from
$12
per visit

Taylor went above and beyond, she was super kind and understanding of our dogs needs. She provided lots of updates and we felt assured that our pets were in safe hands!

Sitter Profile Image: Abi S.
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Sitter Profile Image: Abi S.
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12. Abi S.

I’ll keep up with your pup!
Chicago, IL, 60653
0.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
7 reviews
5 repeat clients
from
$17
per visit

Abi was the best! She is so caring and went above and beyond. When I asked her to check in with me a couple times while I was gone (8 days) she certainly did, and even sent photos which gave me peace of mind! I came home to very happy cats! I cannot recommend her enough. Thank you Abi!!

Sitter Profile Image: Aolani "Catrina" C.
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Sitter Profile Image: Aolani "Catrina" C.
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13. Aolani "Catrina" C.

Star Sitter
Unmatched Care for Your Pets
Hyde Park, Chicago, IL, 60637
1.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
13 reviews
3 repeat clients
from
$22
per visit

Wonderful communication and reports, my cat and dog were both well taken care of! My little dog is a bit of an odd case so it was very nice having someone my dog warmed up to.

Sitter Profile Image: Danielle B.
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Sitter Profile Image: Danielle B.
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14. Danielle B.

I'll care for them all big or small
Hyde Park, Chicago, IL, 60615
0.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
4 reviews
from
$25
per visit

I've known Danielle now for a few years, and I can confidently recommend her as a responsible pet caregiver! Growing up in a home full of dogs, she is no stranger to the hard work and dedication it takes to lovingly care for any pet! And it clearly shows with how happy those dogs are!

Sitter Profile Image: Jabari R.
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Sitter Profile Image: Jabari R.
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15. Jabari R.

Former face to face fundraiser
Chicago, IL, 60615
0.9 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
1 review
from
$16
per visit

Jabari is currently a co-owner of a 8-12 month old Yorkshire Terrier mix currently alongside me whom he frequently feeds, grooms and bonds with on a daily basis. Jabari has experience with both large and small breeds of dogs, he has worked with 1+ year old male Pure breed Cane Corso and 1+ year old female German Shepherd Mix who he has cared for and watched over several times over their life. As well as, already pet-sitting a variety of dogs for many owners within his own family. I would highly recommend Jabari for care for other's pets as he is responsible, caring and diligent about the well-being of all pets and properly caring for them according to their breeds, sizes and ages.

Sitter Profile Image: Alma G.
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Sitter Profile Image: Alma G.
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16. Alma G.

Caring, loving and responsible!
Chicago, IL, 60615
0.7 mi. away
Boarding, Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 reviews
from
$17
per visit

About: My friends, family and neighbors have all counted on me to look after their pets since I was 15 years old. I grew up volunteering in dog shelters and caring for my own pet growing up. I treat all pets as if they were my own! I work full time at a fitness center, but my hours are flexible and I have Fridays and Saturdays off. I typically work later in the mornings and get off in the evenings, but I am able to adjust hours accordingly. I have a cozy apartment with a huge park and dog park 3 minutes away. I make my space work for them and really spend time with them outside and playing as much as they need. My neighborhood is great for those much needed walks!

Sitter Profile Image: Madeleine G.
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Sitter Profile Image: Madeleine G.
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17. Madeleine G.

Dog lover/babysitter for your pup!
Hyde Park, Chicago, IL, 60615
0.5 mi. away
Boarding, Drop-In Visits, Dog Walking
5.0 out of 5 stars
28 reviews
10 repeat clients
from
$16
per visit

Madeleine was great with our dog and was flexible enough to work with our changing schedules. Our dog is used to having someone around all day, so she greatly appreciated the time Madeleine spent with her.

Sitter Profile Image: Chijioke E.
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Sitter Profile Image: Chijioke E.
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18. Chijioke E.

Convenient, Empathetic Care!
Hyde Park, Chicago, IL, 60615
0.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
2 reviews
1 repeat client
from
$18
per visit

Chijioke is one of the most caring and empathetic caregivers I have ever met. My cat easily fell in love and felt safe around them for cuddles and play times. They took extra care to make sure she and her litter space were clean. As well as training her on what are her dedicated spaces versus where she's not allowed like in the bathroom tub lol They have been super helpful in guiding me on how to be a better pet parent every time we meet. Very grateful to have them as my and my cat's best friend!

Sitter Profile Image: Kayla S.
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Sitter Profile Image: Kayla S.
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19. Kayla S.

Star Sitter
✨Pawsome Walks Await✨
Kenwood, Chicago, IL, 60615
0.2 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
30 reviews
15 repeat clients
from
$25
per visit

Kayla did a good job checking in on my cats while I was away. She refilled their water, changed their litter, cleaned up vomit, and played with them.

Sitter Profile Image: Raeanna H.
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Sitter Profile Image: Raeanna H.
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20. Raeanna H.

Pawsitively Caring Pet Sitter
Chicago, IL, 60615
0.1 mi. away
Drop-In Visits, Dog Walking
4.5 out of 5 stars
5 reviews
from
$25
per visit

Raeanna was a great pet sitter. She did all the things I asked of her for my pet. I appreciate that she always gave picture updates of Bagheera and was gentle with him; letting him take his time to get used to her. We had a trouble on the first scheduled day with time, but it was quickly solved. Great work!

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Rover also offers Pet Sitting & Drop Ins in these neighborhoods:

Rover also offers other services in Kenwood:

Pet parents turn to sitters on Rover.com when they're looking for pet-sitting. 7915 owners have reviewed sitters in Kenwood, Chicago, IL, giving them an average rating of 4.9/5. Since 92% of pet owners live within a short drive of a sitter on Rover, it's easy to find the perfect pet sitter near you. 95% of reviewed stays have received a perfect 5-star rating. Wondering how much you can expect to pay on Rover.com? Check out our average pet sitting rates to get an idea before you start a conversation with a pet sitter. Exchange messages from your sitter's profile, ask to schedule a free in-person Meet & Greet, and book and pay on Rover. You'll receive adorable photo updates, premium insurance, and world-class support.

The next time you head out of town and need someone to take care of your pets and check in on you home, turn to Rover. It's easy to find a loving Kenwood pet sitter on Rover who'll give your pet one-on-one attention while you're away, and take care of your home. Search from hundreds of trusted pet sitters in Kenwood, Chicago, read sitter profiles, and reach out to sitters who seem like a good fit for you and your pet(s). We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. Then, when you're ready, book and pay for your house and pet sitter all through Rover: it's easy, safe, and cashless. You'll have the peace of mind knowing that your sitter has free premium insurance, a team of safety experts available 24/7, and will send you cute photo updates throughout the stay. Rover is the easiest way to find trustworthy Kenwood pet sitters and avoid the kennel.

Drop-In Visits