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

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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
House Sitting, Drop-In Visits, Dog Walking
5.0
37 reviews
12 repeat clients
from
$20
per visit

Crystal was amazing with my reactive border collie! She took her time introducing herself and helped Zuri be super comfortable on a walk when she’s not used to being taking out by others!

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
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0
11 reviews
7 repeat clients
from
$17
per visit

Coretta is amazing! She showed so much attention and care to our pets. I’m so grateful to have found her on Rover. She asked great questions and was very kind and accommodating. Highly recommend!

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Sitter Profile Image: David K.
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Sitter Profile Image: David K.
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3.

David K.

Excellent dog/house/cat sitter
Near South Side, Chicago, IL, 60616
House Sitting, Drop-In Visits, Dog Walking
5.0
48 reviews
19 repeat clients
from
$20
per visit

Hired David last second to come take my dog out. He was super accommodating. David was so kind and good with my German shepherd puppy. Sent lots of photos and let me know what was going on. Great communication. Would definitely hire him again! Very genuine, nice guy!

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Sitter Profile Image: Dalila E.
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Sitter Profile Image: Dalila E.
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4.

Dalila E.

Rover 101
PET SPECIALIST
Chicago, IL, 60608
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0
161 reviews
72 repeat clients
from
$24
per visit

We enlist Dalila’s services regularly now that our work schedules have picked up considerably. She’s reliable and been able to come last minute when work threw us a curve ball. She’s been a lifesaver a few times over now and we’re happy to have her as our regular sitter :)

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Sitter Profile Image: Taiyo N.
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Sitter Profile Image: Taiyo N.
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5.

Taiyo N.

Ready to Care for Your Beloved Pet!
Near West Side, Chicago, IL, 60607
House Sitting, Drop-In Visits, Dog Walking
5.0
2 reviews
from
$22
per visit

Taiyo is a very polite, punctual and helpful young man. He looked after our dog very well and I would highly recommend him!

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Sitter Profile Image: Kayla S.
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Sitter Profile Image: Kayla S.
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6.

Kayla S.

✨Pawsome Walks Await✨
Kenwood, Chicago, IL, 60615
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
18 reviews
11 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: Janette V.
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Sitter Profile Image: Janette V.
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7.

Janette V.

People call me Snow White lol
Chicago, IL, 60609
House Sitting, Drop-In Visits, Dog Walking
5.0
6 reviews
3 repeat clients
from
$50
per visit

Janette was amazing, 10/10 recommend her! She accepted my last minute booking on a very busy weekend, communicating quickly and kindly to coordinate the drop-in. She did an amazing job of communicating before, during, & after the drop-in even when I wasn't able to promptly answer her. Janette even went above & beyond - going out on a limb to greet my very scared cats with treats!

Sitter Profile Image: Emily N.
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Sitter Profile Image: Emily N.
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8.

Emily N.

Experience with multiple sized dogs
Bridgeport, Chicago, IL, 60616
House Sitting, Drop-In Visits, Dog Walking
5.0
81 reviews
25 repeat clients
from
$20
per visit

Emily did a great job with my cats! She was very attentive to their needs and spent a lot of time with them, and all of her communication was prompt and thorough. Highly recommend!

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Sitter Profile Image: Quiana L.
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Sitter Profile Image: Quiana L.
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9.

Quiana L.

loves animals more than people lol
Kenwood, CHICAGO, IL, 60615
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
1 review
from
$17
per visit

Quiana has dog sat for me numerous times. She treats my dog as if it’s her own. Always takes him for long walks. Plays endless fetch and even lets my dog sleep in bed with her. Her home is clean and welcoming. She keeps treats on hand even though she doesn’t have a dog. She’s a true dog lover and would be an amazing choice to keep any dog.

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Sitter Profile Image: Madeleine G.
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Sitter Profile Image: Madeleine G.
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10.

Madeleine G.

Dog lover/babysitter for your pup!
Hyde Park, Chicago, IL, 60615
Boarding, Drop-In Visits, Dog Walking
5.0
25 reviews
8 repeat clients
from
$16
per visit

Madeleine has come to look after our fur baby a few times now and has been amazing each time. She’s been punctual, stayed extra if asked, and keeps us updated on the status of our pup. Highly recommend!

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Sitter Profile Image: Taylor C.
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Sitter Profile Image: Taylor C.
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11.

Taylor C.

Energetic dog lover looking to help
Hyde Park, Chicago, IL, 60615
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
10 reviews
3 repeat clients
from
$15
per visit

Taylor was very attentive to my dog because when he came home to me he was very happy and showed no evidence of mistreatment. She was able to take him on a small walk throughout the day and give him ample potty breaks. She was very nice and responsive with her messaging and I would definitely use her as a sitter again.

Sitter Profile Image: Susan C.
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Sitter Profile Image: Susan C.
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12.

Susan C.

You're Dog is My Dog!
Hyde Park, Chicago, IL, 60615
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
126 reviews
56 repeat clients
from
$20
per visit

Susan took excellent care of my two kittens on our week long trip out of state. It was our first time being away from the kittens for more than a day, but I felt reassured after our meet and greet. Susan really does go above and beyond for her clients and their fur babies. 10/10 recommended her :)

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Sitter Profile Image: Zareena M.
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Sitter Profile Image: Zareena M.
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13.

Zareena M.

Chill spot for dogs
Hyde Park, Chicago, IL, 60615
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0
4 reviews
2 repeat clients
from
$15
per visit

Very kind & efficient! Will be booking again! :)

Sitter Profile Image: Amelia H.
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Sitter Profile Image: Amelia H.
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14.

Amelia H.

Long, scenic, fun sniff walks :)
Hyde Park, Chicago, IL, 60615
House Sitting, Drop-In Visits, Dog Walking
5.0
6 reviews
4 repeat clients
from
$30
per visit

Amelia used to watch my black lab Jasmine when I went out of town or on trips. She used to take really good care of Jasmine, and on top of that she would send me Snapchats of what she and Jasmine were doing, which was really nice.

Sitter Profile Image: Elizabeth D.
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Sitter Profile Image: Elizabeth D.
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15.

Elizabeth D.

Does your pet need a new friend?
Douglas, Chicago, IL, 60609
House Sitting, Drop-In Visits, Dog Walking
5.0
16 reviews
4 repeat clients
from
$23
per visit

Elizabeth watched our cat Chachi and she did an amazing job! He’s typically very shy but Elizabeth was so gentle and patient that he immediately warmed up to her. Having Elizabeth watch him gave us a really big sense of relief and made us feel safe leaving him knowing he was in such good hands. I can tell she really cared for him and enjoyed his company. I hope to always use Elizabeth when we’re out of town.

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Sitter Profile Image: Lucy G.
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Sitter Profile Image: Lucy G.
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16.

Lucy G.

Always looking for new paw-friends!
Chicago, IL, 60615
Drop-In Visits, Dog Walking
5.0
16 reviews
2 repeat clients
from
$18
per visit

Lucy did a phenomenal job taking care of our kitties while we were gone! She was consistent, professional, and caring. She sent pictures and a little update every day. I knew my cats were in good hands with her!

Sitter Profile Image: Katherine B.
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Sitter Profile Image: Katherine B.
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17.

Katherine B.

🐶Who's a good dog? Trick question!
Grand Boulevard, Chicago, IL, 60615
House Sitting, Drop-In Visits, Dog Walking
5.0
40 reviews
11 repeat clients
from
$20
per visit

KT was fantastic with our 13 year old cat, Minnow. They immediately connected and it was clear that they have a real love and care for animals. Was also able to schedule with them in rather short notice, which definitely relieved quite a bit of anxiety on our end. Highly recommended.

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Sitter Profile Image: Chi O.
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Sitter Profile Image: Chi O.
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18.

Chi O.

Fun Loving Dog Enthusiast
Grand Boulevard, Chicago, IL, 60653
Drop-In Visits
6 years of experience
from
$18
per visit

About: I love dogs! I always have, and have my own puppy best friend at home with me. I’m so excited to love on your furry friends just as much as I do mine. I love long walks with lots of pauses for sniffing and exploring, and plenty of indoor playtime with my dog Mini. I’m also big on healthy treats and snacks. Aside from my dog, I’ve also had plenty of fun dog-sitting for other dogs of small to medium size. Choose me to give your pup an exciting, dynamic vacation while you’re gone! I’m currently a student at Booth which means that most of my time is free (class on average only 3 hours a day) and I’m close by to check on pups! I am big on walks, pets, and enrichment interactions to keep pups mind as occupied as their body. That being said, I know you know best and I’ll follow your instructions on treats and playtime to disrupt your dogs routine as little as possible.

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Sitter Profile Image: Raeanna H.
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Sitter Profile Image: Raeanna H.
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19.

Raeanna H.

Pawsitively Caring Pet Sitter
Chicago, IL, 60615
House Sitting, Drop-In Visits, Dog Walking
3 reviews
from
$25
per visit

Raeanna is reliable, responsible, and an all-around awesome person! She truly loves animals, and I can always count on her to keep my pets safe and happy while I am away. She also goes above and beyond to keep my home in pristine condition. I will continue to use Raeanna for pet care when the need arises!

Sitter Profile Image: Brian D.
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Sitter Profile Image: Brian D.
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20.

Brian D.

Rover 101
Caring, energetic, and trustworthy!
Hyde Park, Chicago, IL, 60615
Drop-In Visits, Dog Walking
5.0
19 reviews
4 repeat clients
from
$20
per visit

Brian did a drop-in visit to meet our dog Zoey, who has a really hard time with strangers! Zoey was adopted so we don't know her full history, except that she distrusts new people and dogs. Therefore, it's important for us to set up meet and greets that help everyone acclimate to each other, and Brian was a fantastic fit. Brian is detail oriented and inquisitive — he really takes the time to ask questions and learn as much as possible about your fur baby and what has worked - and he is extremely communicative. It was clear that Brian has experience with reactive dogs - and his belief that Zoey was just like any other dog underneath all the reactivity - made us confident that he could succeed in gaining her trust over time. Brian did a great job with Zoey during his meet and greet and we are grateful for his patience and skills!

Search Map

Pet parents turn to sitters on Rover.com when they're looking for pet-sitting. 7,915 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.

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 Kenwood, 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:

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