Dog Boarding in Kenwood, Chicago, IL
Drop off your dog at a sitter’s home or dog boarding center in the morning and pick them up in the evening.
Every sitter passes an enhanced background check. Learn about RoverProtect
Top rated Kenwood dog boarders
“Tamara was amazing and graciously sent pics of my puppy when requested. He was happy and well taken care of. She was excellent when the date I entered was incorrect but still agreed to keep my fur baby once it was corrected. I highly recommend Tamara for pet sitting services.”
“loved getting frequent updates and photos of my puppy! Elizabeth and her family were very flexible and accommodating. My pup had a blast! Definitely will have them sit again!!!”
“Bola did such an amazing job with my PawSon, Zuko! She checked in daily during our trip, kept us aware of any behavior that wasn’t typical to his schedule and sent us lots of cute photos. She’s so kind and gave Zuko soooo much love. We will def be using her again.. she’s family now!”
“OMG she was wonderful. Her space was nice and clean she checked in everyday with me I was running late she assured me it was ok my dog went on play dates and much more. I would definitely be using her every time.”
“Kamiah watched Luna and we couldn't be happier. She sent consistent photos and videos, and it was clear they were having a great time. Luna was so happy when we picked her up, and then promptly fell asleep all night, so I know she was getting at it. Highly recommend! Thank you so much!”
“Linde was great with Wrigley! We were really worried because Wrigley is still adjusting to a new city, but she made sure he (and us) were comfortable with everything. She let Wrigley adjust at his own pace, and sent tons of pics. We’ll definitely be booking again!”
“Katrina was the most amazing pup sitter I’ve ever had! She provided thorough feedback daily, and even sent my pup home with printed photos from his stay! I felt so safe having Katrina watch my dog, and I hope she can always be his designated sitter going forward. She truly went above and beyond and I’m so thankful.”
“Ashley was amazing!! She watched our mini dachshund Ellie for a week and did an incredible job. We got adorable photo updates daily and enjoyed our vacation so much more knowing Ellie was in good hands. Definitely recommend!”
“Penelope’s stay was exceptional! Yeju took such amazing care of her while we were away, we didn’t worry one bit while out of town. We received daily photo and progress updates, and she even sent her home with cookies! Will absolutely be booking again when we travel.”
“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!!”
“Lisette was awesome! I always felt confident that my pup was in good hands and she was great with communication & updates. She was also accommodating with pickup & dropoff times, which was a plus. Would definitely love to have Jax stay with her again! Thanks, Lisette 😌”
“My pup Lucy always loves stays with Stacey and her Boxer, Joe. Stacey sends lots of great pics- and cares for Lucy just as I would, if not better! She's always my first choice to watch Lucy.”
“Lan was absolutely amazing with our pup Goose for a last minute 10 day stay! He got lots of attention and we got a lot of pictures and updates! Lan followed all the care instructions perfectly and we couldn’t have asked for more! We highly recommend Lan for any pet care you might need!!”
“Dwight was fantastic. I have a very adorable but very playful puppy and he took great care of her. While I was on vacation he kept me updated at my request and sent pictures. Absolutely would recommend and plan to re-book Dwight in the future! Thank you again for your kindness and hospital with my furry BFF.”
“Toojan was awesome with BMO! She really knows her stuff when it comes to cats and was super attentive to what BMO needed. Loved getting daily pics and little updates on how BMO was settling in. She’s also just really sweet. Would totally book again and definitely recommend!”
“Kyle and Ben were great! Our dog loves them and seems to have had a great time with their dogs and cats. Kyle and Ben board many dogs in our neighborhood and everyone has great things to say about them. It was relief to know our dog was in a home environment with nice, trustworthy people.”
“Simply the BEST! My dog didn’t want to get in the car to leave! Katherine had a nice big yard and a pup Colby who clearly entertained my Tully. I received lots of pictures while I was gone and I was kept updated just enough so I could relax during my time away. I will be booking again!”
“Theo not only loved his playmates but Dani & Kyle were very present putting the dogs’ needs first. Good and frequent walks, lots of family time and continued videos & pics! We will return, Theo is still smiling.”
“Tiffany is a great sitter and we won't even plan anything unless she can watch our dog now. She sends the cutest pictures and videos and you can tell she treats Simba as her own.”
Loving dog boarding in your neighborhood
Search Results
Tamara J.Star Sitter
“Tamara was amazing and graciously sent pics of my puppy when requested. He was happy and well taken care of. She was excellent when the date I entered was incorrect but still agreed to keep my fur baby once it was corrected. I highly recommend Tamara for pet sitting services.”
E K.
“loved getting frequent updates and photos of my puppy! Elizabeth and her family were very flexible and accommodating. My pup had a blast! Definitely will have them sit again!!!”
Bola A.Star Sitter
“Bola did such an amazing job with my PawSon, Zuko! She checked in daily during our trip, kept us aware of any behavior that wasn’t typical to his schedule and sent us lots of cute photos. She’s so kind and gave Zuko soooo much love. We will def be using her again.. she’s family now!”
Emily S.Star Sitter
“Emily was amazing - accommodating, on time, and so sweet to send photos throughout the day while I was at work. Would 100% book again - thank you Emily!”
Daphnay S.Star Sitter
“OMG she was wonderful. Her space was nice and clean she checked in everyday with me I was running late she assured me it was ok my dog went on play dates and much more. I would definitely be using her every time.”
Kamiah & Casius D.Star Sitter
“Kamiah watched Luna and we couldn't be happier. She sent consistent photos and videos, and it was clear they were having a great time. Luna was so happy when we picked her up, and then promptly fell asleep all night, so I know she was getting at it. Highly recommend! Thank you so much!”
Linde L.Star Sitter
“Linde was great with Wrigley! We were really worried because Wrigley is still adjusting to a new city, but she made sure he (and us) were comfortable with everything. She let Wrigley adjust at his own pace, and sent tons of pics. We’ll definitely be booking again!”
Hua “Katrina” F.Star Sitter
“Katrina was the most amazing pup sitter I’ve ever had! She provided thorough feedback daily, and even sent my pup home with printed photos from his stay! I felt so safe having Katrina watch my dog, and I hope she can always be his designated sitter going forward. She truly went above and beyond and I’m so thankful.”
Ashley M.Star Sitter
“Ashley was amazing!! She watched our mini dachshund Ellie for a week and did an incredible job. We got adorable photo updates daily and enjoyed our vacation so much more knowing Ellie was in good hands. Definitely recommend!”
Yeju K.
“Penelope’s stay was exceptional! Yeju took such amazing care of her while we were away, we didn’t worry one bit while out of town. We received daily photo and progress updates, and she even sent her home with cookies! Will absolutely be booking again when we travel.”
Ashley B.Star Sitter
“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!!”
Lisette S.Star Sitter
“Lisette was awesome! I always felt confident that my pup was in good hands and she was great with communication & updates. She was also accommodating with pickup & dropoff times, which was a plus. Would definitely love to have Jax stay with her again! Thanks, Lisette 😌”
Stacey R.
“My pup Lucy always loves stays with Stacey and her Boxer, Joe. Stacey sends lots of great pics- and cares for Lucy just as I would, if not better! She's always my first choice to watch Lucy.”
Lan P.Star Sitter
“Lan was absolutely amazing with our pup Goose for a last minute 10 day stay! He got lots of attention and we got a lot of pictures and updates! Lan followed all the care instructions perfectly and we couldn’t have asked for more! We highly recommend Lan for any pet care you might need!!”
Dwight C.Star Sitter
“Dwight was fantastic. I have a very adorable but very playful puppy and he took great care of her. While I was on vacation he kept me updated at my request and sent pictures. Absolutely would recommend and plan to re-book Dwight in the future! Thank you again for your kindness and hospital with my furry BFF.”
Toojan A.Star Sitter
“Toojan was awesome with BMO! She really knows her stuff when it comes to cats and was super attentive to what BMO needed. Loved getting daily pics and little updates on how BMO was settling in. She’s also just really sweet. Would totally book again and definitely recommend!”
Kyle H.
“Kyle and Ben were great! Our dog loves them and seems to have had a great time with their dogs and cats. Kyle and Ben board many dogs in our neighborhood and everyone has great things to say about them. It was relief to know our dog was in a home environment with nice, trustworthy people.”
Katherine C.Star Sitter
“Simply the BEST! My dog didn’t want to get in the car to leave! Katherine had a nice big yard and a pup Colby who clearly entertained my Tully. I received lots of pictures while I was gone and I was kept updated just enough so I could relax during my time away. I will be booking again!”
Dani B.Star Sitter
“Theo not only loved his playmates but Dani & Kyle were very present putting the dogs’ needs first. Good and frequent walks, lots of family time and continued videos & pics! We will return, Theo is still smiling.”
Tiffany O.
“Tiffany is a great sitter and we won't even plan anything unless she can watch our dog now. She sends the cutest pictures and videos and you can tell she treats Simba as her own.”
Kenwood dog parents share their Rover experiences
I chose Willy because of his proximity to me, his reviews, and his rates. He is kind and accommodating. I actually confirmed with him a bit later than I said I would but he still graciously accepted our two pups. It’s true what others say that he sends lots of pics. In just a 24 hour period we got pictures in the afternoon, the evening and the next morning. And from the looks of things, Willy actively engaged with the pups the whole time; they’re not just left out in the yard. I think the most important thing for me is that my dogs will have the same kind of experience that they enjoy at home, including plenty of human contact. I think that’s why we all choose in-home boarders, right? And that’s exactly what they got. Anybody who can engage and stimulate a loud, demanding, beagle bark machine gets 5 stars from me every time. I would book with again.
Kamiah & Casius were great with my fur baby. It was my first time using a service like this and I was so nervous. Kamiah was understanding of my nerves answered all my questions. She sent daily photos and videos. She was understandable with my travel delays and when I picked my dog up she was smiling and continued to do so for the rest of the evening. There were no stress signals or behaviors from my dog and she was right back into her routine at home. Thank you for taking such great care of Macci!! Will definitely use again
Tiffany was amazing! My first time boarding and she did an amazing job all while easing my fears. Tiffany provided up to date pictures and took care of my baby as if he was her own. Book with Tiffany you will not be disappointed. For the price and care! I will always boom with Tiffany! Thank you!!!
Dwight was great! He looked after my two pups while I was away on a family vacation. I could tell that he took the time to get to know both of them and treated them like extended family. He sent picture updates and was flexible with the drop off time. Next time I have to go out of town, I’m def booking with Dwight!
If you are seeking a great sitter or dog walker, look no further! Dashawn is an amazing sitter and genuinely like animals. He is very communicative, would send me updates and was more than happy to accommodate my special requests. It was my first time leaving my pooch with a non family member and I wouldn't hesitate to use Shawn again!
Popular requests near you
Select a filter and find qualifying Kenwood sitters!How Rover works
1. Search
Read verified reviews by dog parents like you and choose a boarder who’s a great match for you and your dogs
2. Meet & Greet
Meet either virtually or in-person with a boarder to discuss the level of care needed for your dogs while you’re away
3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
Why Choose Rover?
Cashless payments
Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn’t happen often, but if your dog boarding sitter has to cancel, we’ll work with you to find a new dog boarding sitter.
World-class support
We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Dog Boarding FAQs
Frequently asked questions about Rover
Only Rover provides comprehensive Kenwood dog boarding options that meet your dog's unique needs. Anxious or special needs dogs who prefer a 1:1 environment are a good fit for in-home dog boarding, while energetic pups who benefit from socialization and activity are a good fit for dog boarding facilities.
Typically, dog boarding sitters on Rover respond in under an hour, so you should be matched with the perfect sitter for you and your dog in no time!
Experience can vary widely from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when comparing sitters available in Kenwood.
Rover makes it easy to find Kenwood dog boarding sitters to provide loving care from their own home. The background-checked, 5-star sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog boarding is great for:
- Dogs of all ages and abilities, including puppies
- Pet parents looking for a safe, loving alternative to a kennel
- Dogs who’d love to socialize with their sitter’s pets
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog boarding sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your dog boarding sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your dog boarding service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.
Connect anywhere with the Rover app
