Dog Boarding in Kenwood, Chicago

Find a loving dog sitter to watch your dog overnight at your sitter's home.

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House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
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Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Makeba L.
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Sitter Profile Image: Makeba L.
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1. Makeba L.

Star Sitter
WFH, Tiny Tail Friends
Kenwood, Chicago, IL, 60615
0.2 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
15 reviews
11 repeat clients
from
$47
per night

Ms. Makeba was great with my fur baby, she sent pictures everyday and gave me updates while my senior baby was in her care. Thank you so much for taking care of my Chole. I will definitely be calling on you again Ms Makeba.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Kyle H.
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Sitter Profile Image: Kyle H.
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2. Kyle H.

Rover 101
Over a decade of experience!
Hyde Park, Chicago, IL, 60615
0.8 mi. away
Boarding
5.0 out of 5 stars
16 reviews
4 repeat clients
from
$55
per night

My dog has boarded with Kyle a few times and is always sooo happy to see her. She clearly has a way with dogs. I would recommend her and definitely use her again.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: E K.
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Sitter Profile Image: E K.
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3. E K.

Rover 101
Star Sitter
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
247 reviews
107 repeat clients
from
$45
per night

It was our first time using Rover and having Elizabeth watch our very energetic 8 month old Lab/Hound Pup. I cannot recommend highly enough the care that our dog Oliver received while we were gone. Elizabeth and her family took such loving care of our dog while we were away with lots of walks, snuggles, and a few treats too :) Thank you for watching our pup while we were gone and I know next time we are away Oliver will be so happy to spend time with his new friends!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Ebonee A.
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Sitter Profile Image: Ebonee A.
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4. Ebonee A.

Star Sitter
12 + years of Vet-Tech experience!
Hyde Park, Chicago, IL, 60615
1.1 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
30 reviews
15 repeat clients
from
$50
per night

This is the second time we've used Ebonee. She's a great communicator, friendly, and prompt. She always sends plenty of updates and photos. When you first meet with her, she asks great questions and wants to get to know your pup. I definitely recommend Ebonee with your dog and we'll be sure to think of her in the future for ours.

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Sitter Profile Image: Tania B.
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Sitter Profile Image: Tania B.
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5. Tania B.

Rover 101
Star Sitter
Home of The Kikster Scissorpaws.
McKinley Park, Chicago, IL, 60609
4.7 mi. away
Boarding
5.0 out of 5 stars
34 reviews
9 repeat clients
from
$50
per night

Tania was great with my little guy! He is an anxious pup and he seemed to do really well with her. She communicated throughout his stay, sent lots of pics, and was very accommodating. I will definitely be using her again!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: MariaJose R.
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Sitter Profile Image: MariaJose R.
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6. MariaJose R.

Law student who loves all pups!
Washington Park, Chicago, IL, 60623
1.4 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
14 reviews
2 repeat clients
from
$40
per night

My dog was taken care off even though she is particular with her habits. María José always keep me updated and made me feel good and at easy while I was out of town. Thank you!

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Sitter Profile Image: Ashley M.
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Sitter Profile Image: Ashley M.
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7. Ashley M.

Rover 101
Star Sitter
WFH, pet loving, porch, parks!
Lower West Side, Chicago, IL, 60608
4.7 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
44 reviews
19 repeat clients
from
$52
per night

Ashley was great and took great care of our dog. She was communicative and sent a bunch of photos to make sure we were updated on how he was doing. Took him to the dog park, on walks, etc. Made us feel completely at ease while we were on a trip.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Willy J.
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Sitter Profile Image: Willy J.
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8. Willy J.

Reliable Dog Lover at your Service
Douglas, Chicago, IL, 60653
1.9 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
16 reviews
4 repeat clients
from
$45
per night

Very accommodating, even for a last minute request. Kept me updated on things that could be of concern (my girl refused to eat because she’s dramatic) and sent pics/videos throughout the stay! Would recommend. Thank you again

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Sitter Profile Image: Ann-Marie H.
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Sitter Profile Image: Ann-Marie H.
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9. Ann-Marie H.

Pet Auntie Extraordinaire
Near South Side, Chicago, IL, 60605
3.9 mi. away
Boarding, Drop-In Visits, Dog Walking
5.0 out of 5 stars
13 reviews
3 repeat clients
from
$55
per night

Ann-Marie was great with our dog! He has warmed up to her so well and she is so caring with him. We appreciate the occasional update from Ann-Marie, and whenever we ask questions, she replies. She is so amenable to the pick-up and drop-off schedule, especially if our flights get delayed. She has been a great caretaker for him for both weekend getaways and week-long trips, highly recommend to other owners!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Ashley B.
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Sitter Profile Image: Ashley B.
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10. Ashley B.

Star Sitter
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
79 reviews
38 repeat clients
from
$75
per night

Ashley B. was phenomenal with our dogs. They came back home happy and well rested. Our tiny dog is very anxious and can be hard to deal with so we truly appreciate her!! She sent photo and video updates and was great with communication leading up to booking and during the stay. Will definitely book with her and her family again! Book with Ashley B - you and your pups will not be disappointed!!

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Sitter Profile Image: Rachel W.
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Sitter Profile Image: Rachel W.
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11. Rachel W.

Star Sitter
Dog Walker for 5 Years
Near South Side, Chicago, IL, 60616
3.4 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
42 reviews
17 repeat clients
from
$60
per night

Rachel was an excellent sitter. She sent many pictures of my dog & took him to the dog park to socialize. Great communication skills & was available for drop off and pickup time when needed. I recommend Rachel to others looking for a reliable sitter.

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Sitter Profile Image: Gillian K.
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Sitter Profile Image: Gillian K.
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12. Gillian K.

Star Sitter
Loves long walks and fluffy friends
Bridgeport, Chicago, IL, 60608
4.1 mi. away
Boarding
5.0 out of 5 stars
18 reviews
7 repeat clients
from
$40
per night

Walter LOVED being with Gillian and Dillon. They took amazing care of him and were amazing updates though out the whole time I was gone. Walter came back happy, healthy and tired!!! We can’t wait to go back!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Jason M.
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Sitter Profile Image: Jason M.
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13. Jason M.

Experienced Professional
Lower West Side, Chicago, IL, 60608
4.5 mi. away
Boarding, Dog Walking
12 reviews
from
$50
per night

I would recommend Jason for any pet owner. Simply because he genuinely loves pets and cares for their well being. I have been a client of his for years and whenever I drop off Zeus it’s like I’m leaving him at his second home. He’s an excellent trainer but most Importantly he makes sure the animals in his care are comfortable and having fun! Call Jason!

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Sitter Profile Image: Briana V.
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Sitter Profile Image: Briana V.
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14. Briana V.

Star Sitter
Always home, 24/7 attention & care!
South Lawndale, Chicago, IL, 60623
6.5 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
47 reviews
13 repeat clients
from
$48
per night

Thank you Briana for making Blanca feel at home away from home. She made sure I knew my girl was ok and happy. I highly recommend her and I’ll be using her fing forward.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Holly R.
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Sitter Profile Image: Holly R.
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15. Holly R.

Your Pet's Extended (WFH) Family
Woodlawn, Chicago, IL, 60637
2.6 mi. away
Boarding, Drop-In Visits, Doggy Day Care
5.0 out of 5 stars
78 reviews
35 repeat clients
from
$60
per night

It feels good to not only know Iggy is well taken care of at Holly’s place, but also enjoys his time while staying there. Thank you for taking good care of our good boy as you always do.

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Sitter Profile Image: Katie M.
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Sitter Profile Image: Katie M.
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16. Katie M.

Star Sitter
Long time animal lover
Near North Side, Chicago, IL, 60610
7.0 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
164 reviews
56 repeat clients
from
$45
per night

I felt super comfortable leaving Kira with Katie and Java for a weekend trip. She was really responsive and sent pictures of the doggos having a great time together. Kira came back to me relaxed and tired from a great weekend. I'll definitely book her again for future trips.

Sitter Profile Image: Kayla S.
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Sitter Profile Image: Kayla S.
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17. 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
$55
per night

This was our second time staying with Kayla and it was just as great as the first! Highly recommend! She is very caring and goes above and beyond!

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Sitter Profile Image: Melanie S.
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Sitter Profile Image: Melanie S.
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18. Melanie S.

Experienced Dog Owner and Dog Lover
Near North Side, Chicago, IL, 60654
6.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
158 reviews
62 repeat clients
from
$55
per night

Melanie was great and very friendly with Wally. We got regular updates and pictures. It was only for a weekend but will definitely use her services again in the future.

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Sitter Profile Image: Bola A.
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Sitter Profile Image: Bola A.
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19. Bola A.

Star Sitter
Big time dog lover 😄
Hyde Park, Chicago, IL, 60615
1.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
24 reviews
6 repeat clients
from
$40
per night

Bola have given me such peace of mind when we have to leave our dog for 9 days. Always give the best updates and pictures, and I can rest easy knowing my little buddy is taken care of. Couldn’t recommend enough and would definitely use her again. ❤️❤️❤️

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Sitter Profile Image: Regan D.
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Sitter Profile Image: Regan D.
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20. Regan D.

Star Sitter
Your friendly neighborhood pet girl
Near North Side, Chicago, IL, 60654
6.0 mi. away
Boarding, Dog Walking
5.0 out of 5 stars
34 reviews
14 repeat clients
from
$45
per night

Regan and her boyfriend were great with Penny! They sent me lots of photo updates and Penny got plenty of time with them at home / watching Sunday football. Penny enjoyed her stay and I felt very comfortable that she was in good hands.

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Dog lovers in Kenwood, Chicago, IL love dog sitters on Rover.com. Over 7915 pet owners have reviewed dog sitters on Rover in Chicago, giving them an average rating of 4.9/5 stars. No matter what your price range is, you might be surprised to learn how affordable dog boarding in Chicago can be when you book with Rover. Wondering how much it might cost to book dog boarding? Check out our average dog boarding rates to get an idea before contacting a dog sitter near you.

Rover.com is the simple, savvy way to find and book Kenwood dog boarding. It's easy to find the perfect dog sitter. Many sitters on Rover have a long history of dog sitting, and 95% of reviewed stays have received a perfect five-star rating. When you book dog boarding on Rover, your dog will enjoy a loving staycation in their sitter's home. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Every dog sitter in Kenwood, Chicago, IL has the option to complete a free background check. Stays are booked on Rover every minute of every day, and more than 92% of the population lives within a short drive of one of the more than 75,000 sitters who've listed their services on Rover. When you book Kenwood dog boarding on Rover, your dog gets the loving care they deserve, and you get peace of mind.

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