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: Easter Weekend
Sitter Profile Image: Coretta S.
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Sitter Profile Image: Coretta S.
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1. 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
46 reviews
16 repeat clients
from
$17
per visit

We highly recommend Coretta! She was very deliberate with each step in getting to know our expectations and in meeting our cat. Our cat is very active and gets lonely when we’re not home, but we had nothing to worry about because Coretta made him so happy:) She gave us updates and sent pictures from every visit. We will definitely seek her services next time we need a cat sitter!

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Sitter Profile Image: Crystal R.
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Sitter Profile Image: Crystal R.
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2. 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
83 reviews
36 repeat clients
from
$21
per visit

Crystal arrived promptly for both the meet'n'greet and drop-in and our dogs took to her right away. She was friendly, professional and easy to communicate with. She sent photos of the dogs while she was here which is always helpful and reassuring! One of our dogs is a blind senior and she handled that well.

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Sitter Profile Image: Nycol H.
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Sitter Profile Image: Nycol H.
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3. Nycol H.

Hi, I’m Nycol!
Hyde Park, Chicago, IL, 60615
0.7 mi. away
House Sitting, Drop-In Visits
from
$25
per visit

Nycol is incredibly responsible and caring towards both animals and humans! Nycol has watched over our dear Sadie and Bernie for the last 2 years and she is still the only one we trust to watch them! I’m immensely grateful for Nycol and the bond she shares with our loving fur babies.

Confirmed availability: Easter Weekend
Sitter Profile Image: Elizabeth D.
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Sitter Profile Image: Elizabeth D.
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4. 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
23 reviews
5 repeat clients
from
$23
per visit

Levi took excellent care of my pups! She's extremely knowledgeable about pet care and very communicative! I'll definitely be utilizing her services again in the near future!

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Sitter Profile Image: Katherine B.
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Sitter Profile Image: Katherine B.
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5. 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
54 reviews
15 repeat clients
from
$20
per visit

Katherine is wonderful! We have a new kitten and an older fella cat, we had to leave town for a week, and weren't sure how the kitten would respond to his first time with us being away, how many things would be broken, and who could be a good fit to keep an eye on things and make sure the boys were well cared for. Katherine is an excellent communicator, provides tons of great information during visits, and gave us peace of mind that our home and kitties were in good hands. If Katherine is available, you'll be lucky to have them!

Confirmed availability: Easter Weekend
Sitter Profile Image: Aolani "Catrina" C.
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Sitter Profile Image: Aolani "Catrina" C.
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6. Aolani "Catrina" C.

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
12 reviews
3 repeat clients
from
$22
per visit

This is my second time booking Catrina, and will continue to book with her! My dog is a little funny with new people, but she has been able to handle her very well and I can tell my pup is comfortable and happy. The communication is always fantastic, and my cat even loves to come out from hiding to get some pets and love. If the cat likes you, that’s a good sign.

Confirmed availability: Easter Weekend
Sitter Profile Image: Leah C.
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Sitter Profile Image: Leah C.
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7. 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.

Confirmed availability: Easter Weekend
Sitter Profile Image: Ashley B.
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Sitter Profile Image: Ashley B.
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8. Ashley B.

Open house for Pets
Hyde Park, Chicago, IL, 60615
0.9 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
67 reviews
38 repeat clients
from
$40
per visit

We are so appreciative of ashley! Very quick responses and lots of updates. Buddy is always happy to see Ashley and her family!

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Sitter Profile Image: Kayla S.
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Sitter Profile Image: Kayla S.
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9. Kayla S.

✨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 fine job taking care of my two cats. She was prompt and consistent following my directions. Taking photos and posting them was a surprise bonus. I'm fully satisfied with Kayla and will book her again when I need help.

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Sitter Profile Image: Olivia A.
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Sitter Profile Image: Olivia A.
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10. Olivia A.

Flexible and reliable pet sitter!
Chicago, IL, 60615
0.8 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
2 reviews
from
$17
per visit

Olivia did a great job checking in on both my cat and my dog. Both the cat and the dog are shy and usually take a while to warm up to new people, but they both seemed to love Olivia. She was also very communicative and sent a great pic of my guys. Highly recommend, ill definitely be rebooking next time I need a drop in.

Confirmed availability: Easter Weekend
Sitter Profile Image: Emily L.
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Sitter Profile Image: Emily L.
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11. Emily L.

Love all pets 🫶
Hyde Park, Chicago, IL, 60637
1.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
3 reviews
from
$20
per visit

Emily was amazing. She was responsive, prompt, and so sweet. We will 100% be hiring her again to come check on our cat!!

Confirmed availability: Easter Weekend
Sitter Profile Image: Dana K.
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Sitter Profile Image: Dana K.
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12. Dana K.

Young professional who loves pets
Hyde Park, Chicago, IL, 60615
0.6 mi. away
Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
3 reviews
3 repeat clients
from
$30
per visit

Dana was fantastic! She took excellent care of my cats and sent photos everyday. Would definitely recommend her!

Confirmed availability: Easter Weekend
Sitter Profile Image: E K.
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Sitter Profile Image: E K.
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13. E K.

Rover 101
Animal Loving Family
Grand Boulevard, Chicago, IL, 60653
1.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
241 reviews
104 repeat clients
from
$45
per visit

She was great! Took great care of our big, energetic dog. Would definitely book again

Confirmed availability: Easter Weekend
Sitter Profile Image: Caitlin S.
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Sitter Profile Image: Caitlin S.
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14. 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 great! She helped me out with a last minute request for my cat, Bailey, and sent lots of photo/video updates. Bailey isn’t a huge fan of new friends but found one in Caitlin only after a couple of days of me being away. I was truly impressed. I couldn’t ask for a better sitter!

Confirmed availability: Easter Weekend
Sitter Profile Image: Joshua M.
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Sitter Profile Image: Joshua M.
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15. Joshua M.

Fun loving animal person
Chicago, IL, 60653
0.9 mi. away
Drop-In Visits, Dog Walking
2 years of experience
from
$17
per visit

About: I have been a dog owner and have had dogs and some cats since the age of 5. I have cared for, paid, and even traveled with a Shih Tzu breed that I currently have, and have had many Doberman Pinschers in the past. I feed, bathe, take them to the park for play and walk, and even watched my neighbor's pets while they were gone. I'm currently working part-time remotely on the days of Monday-Friuay. However, I do have time to take dogs for a walk on weekends after 10 am. I have a fenced yard and a friendly Shih Tzu who is people-friendly and also makes sure she is not exposed to objects in the yard or house. I also have a bed in the living room and her own in my room for comfort. She also takes Heartguard for prevention of fleas, ticks, and ring worm and is rabies vaccinated.

Confirmed availability: Easter Weekend
Sitter Profile Image: Jasmine P.
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Sitter Profile Image: Jasmine P.
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16. Jasmine P.

Rover 101
Beloved dog & cat whisperer, is me!
Chicago, IL, 60615
0.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
58 reviews
21 repeat clients
from
$30
per visit

Jasmine really put me at ease with dropping in on my new doggo, Bingsoo. She was kind and caring and knowledgeable. She was attentive to special needs and a great communicator. Dog whisperer forreal!

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Sitter Profile Image: Abi S.
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Sitter Profile Image: Abi S.
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17. 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
6 reviews
1 repeat client
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: Kahrion M.
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Sitter Profile Image: Kahrion M.
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18. Kahrion M.

Dog lover of all sizes and breeds
Grand Boulevard, Chicago, IL, 60653
1.0 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
3 reviews
from
$30
per visit

Kahrion is very responsible and loving dog parent. He is very attentive to detail and will love your pet as if it is his. His current pets are trained and well behaved.

Confirmed availability: Easter Weekend
Sitter Profile Image: Kayleigh P.
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Sitter Profile Image: Kayleigh P.
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19. Kayleigh P.

Long-time animal lover
Hyde Park, Chicago, IL, 60615
0.5 mi. away
Drop-In Visits
5.0 out of 5 stars
5 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!!!

Confirmed availability: Easter Weekend
Sitter Profile Image: Anahi S.
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Sitter Profile Image: Anahi S.
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20. Anahi S.

Looking to help other pet-owners!
Chicago, IL, 60615
0.5 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
12 reviews
1 repeat client
from
$25
per visit

Anahi is a responsible, dog loving individual who would be a phenomenal dog sitter. Has so much experience with dogs that stems from a true love for them. Has experience living and caring for multiple dogs, and is always in households with them. Can not emphasize more how awesome Anahi is and will be around your dogs as well.

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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