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
Which dates do you need?
What size are your dogs (lbs)?

Search Results

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Crystal R.
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Sitter Profile Image: Crystal R.
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1. Crystal R.

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
89 reviews
39 repeat clients
from
$21
per visit

She was very flexible with our schedule and when we asked her if she could extend she had no issue whatsoever with it. She gave us constant updates and communication and when my dog ripped open a bag she let us know and took it out. I would highly recommend Crystal to anyone.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Coretta S.
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Sitter Profile Image: Coretta S.
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2. Coretta S.

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
55 reviews
19 repeat clients
from
$17
per visit

Coretta is great! Appreciated the care she showed my cats, as well as her updates while I was traveling. Felt so much better leaving the country knowing they were being cared for so well.

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

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
114 reviews
36 repeat clients
from
$20
per visit

This past weekend was the first time Emily took care of my two cats and she was amazing. I left her a list of Kitty To Do’s and sticky notes all over the house lol and she knocked it all out at each visit. Unfortunately one of my cats is a super picky eater and you have to try a couple things for him to eat and she tried it all until he ate not once but twice then she would leave. She made my trip less stressful because I knew my boys where in good hands. She also is a great photographer, I received multiple pics of my boys at each visit which made my day!

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Sitter Profile Image: Taylor L.
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Sitter Profile Image: Taylor L.
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4. 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
3 reviews
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!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Juan-Pablo A.
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Sitter Profile Image: Juan-Pablo A.
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5. 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.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Elizabeth D.
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Sitter Profile Image: Elizabeth D.
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6. 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: Katherine B.
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Sitter Profile Image: Katherine B.
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7. Katherine B.

🐶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

KT was the best with our two kitties! They gave great photo/video updates and communicated with me about any questions/issues that arose. They had a calm presence and the cats seemed to like them immediately. Will definitely book KT again in the future!

Sitter Profile Image: Elizabeth H.
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Sitter Profile Image: Elizabeth H.
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8. 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

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Chijioke E.
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Sitter Profile Image: Chijioke E.
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9. Chijioke E.

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

I highly recommend Chijioke for pet sitting. They are so reliable and caring!! I have booked them multiple times to pet sit for me while I've been out of town and they do a fantastic job every time! They cleaned the litter, fed and kept my cat company. Chijioke is a great communicator, they are thorough and easy to talk to! Plus they kept me updated throughout! A superstar pet sitter! Highly recommend 10/10!

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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!!!

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Sitter Profile Image: Abi S.
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Sitter Profile Image: Abi S.
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11. 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
4 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!!

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Sitter Profile Image: Madeleine G.
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Sitter Profile Image: Madeleine G.
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12. 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.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Jabari R.
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Sitter Profile Image: Jabari R.
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13. Jabari R.

Former face to face fundraiser
Chicago, IL, 60615
0.9 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
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.

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Sitter Profile Image: Leah C.
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Sitter Profile Image: Leah C.
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14. Leah C.

Grad Student & Animal Lover
Hyde Park, Chicago, IL, 60637
1.2 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
5 reviews
3 repeat clients
from
$25
per visit

Leah was great! She was showed up for feedings exactly when we requested, and her updates and photos let us know that our fur babies were cared for with attention and love! We were able to relax and enjoy our time away knowing they were in great hands.

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Sitter Profile Image: Mayela E.
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Sitter Profile Image: Mayela E.
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15. Mayela E.

I’d like to be a dog in other lives
Hyde Park, Chicago, IL, 60615
1.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
11 reviews
4 repeat clients
from
$20
per visit

Stellar cat-sitter! Absolutely recommend, even for elderly cats with special needs :)

Sitter Profile Image: Anna K.
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Sitter Profile Image: Anna K.
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16. Anna K.

Cat mom who loves dogs too
Chicago, IL, 60637
1.0 mi. away
Drop-In Visits, Dog Walking
from
$17
per visit

Anna was a very good dog sitter for our black Labrador Dora. I felt safe and comforted knowing she was being well looked after. Anna is very careful at keeping her safe but also made sure she had lots of fun on walks. Would definitely recommend to others, so would Dora!

Sitter Profile Image: Alma G.
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Sitter Profile Image: Alma G.
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17. 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
3 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!

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Sitter Profile Image: Caitlin S.
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Sitter Profile Image: Caitlin S.
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18. Caitlin S.

Here to look after your furbabies!
Hyde Park, Chicago, IL, 60615
0.6 mi. away
House Sitting, Drop-In Visits
5.0 out of 5 stars
8 reviews
3 repeat clients
from
$17
per visit

Caitlin was wonderful with our two cats. They can be standoffish but she won them over immediately. They seemed unbothered that we went out of town. We will use Caitlin again. She's responsive, detail-oriented, and punctual. She kept our cats schedule, critical for alleviating their (our?) anxiety!

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Sitter Profile Image: Danielle B.
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Sitter Profile Image: Danielle B.
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19. 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
from
$25
per visit

Being an animal lover myself, I can wholeheartedly vouch for Danielle as the perfect pet sitter. Her genuine love for furry pets is unparalleled, making her not just the perfect caregiver, but also a trusted companion to your beloved pets. Danielle has an innate understanding of animals' needs and behaviours as she has grown up and lived with pets her whole life. She will ensure that your pets will feel comfortable and loved for in her care. Her responsible and attentive nature means you can rest assured knowing that your furry family members are in the best hands possible. What sets Danielle apart is her unwavering dedication to the well-being of animals. Whether it's going the extra mile to ensure they get enough exercise, providing them with affectionate cuddles, or even just spending quality time with them, Danielle treats every pet as if they were her own. I have seen firsthand the joy and peace of mind Danielle brings to pet owners. With Danielle as your pet sitter, you can enjoy your time away knowing that your pets are not just looked after, but genuinely cared for. Go Danielle! <3

Sitter Profile Image: Charles P.
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Sitter Profile Image: Charles P.
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20. Charles P.

Lover of 4 legged friends
Kenwood, Chicago, IL, 60615
0.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$17
per visit

Charles is one of the most caring people that someone could entrust their pet with. In addition to the dedication that he shows to his own pet, he has the utmost respect for all creatures even down to the smallest insect. He is very attentive and detail-oriented, especially as it relates to the needs or wants of animals. Finally, he is dependable and would be an excellent steward for anyone's pets.

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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