Dog Boarding in Kenwood, Chicago, IL
Find a loving dog sitter to watch your dog overnight at your sitter's home.

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Top rated Kenwood dog boarders
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

“Dwight did a really good job making me feel comfortable about Gigis stay. She's a skittish dog and he took the time to let her warm up and get adjusted. The recaps and pics he sent were very detailed. I will definitely be rebooking!”


“Yeju and her sister Enye spoiled our dog more than we do when they look after her for 12 days. They constantly sent pictures and videos of her. They were holding her in their arms like a baby in these pictures and it was extremely sweet to see that bonding, because our dog is very timid and not so good with people other than us. They played catch with Lily, that was also amazing because we don't do that because we don't think that Lily is interested in playing anymore since she is 16.5 Lily came home as a very happy dog. She had a wonderful vacation with her new sisters Yeju and Enye. We will definitely let them dog-sit Lily during our travels in the future. We HIGHLY recommend them.”

“Timothy was a wonderful sitter ! He shared updates and photos regularly and gave my dog extra food because I didn’t pack enough. He was also very gracious to let me extend my booking on short notice due to travel delays. Highly recommend Timothy and hope we can book with him again !”

“Eric and Eunjin took such great care of Cooper for a full week and went above and beyond to make sure Cooper was happy, comfortable and loved. I got regular updates and photos, and it was clear that Cooper was having a great time. They are very reliable, responsive, and genuinely kind. I felt totally at ease being away, and I’d trust them again for future stays!”

“Rina was a great sitter for my little prince, she was very accommodating at the last minute and I really appreciate her help. She sent me pics and kept me updated the whole time.”

“Nate was so accommodating and friendly throughout the entire process. He obviously took great care of my pup. I would absolutely use Nate again and recommend him to anyone!”


“This was Chase's second time with Ashley and it was just as good as the first! She is very attentive and sends plenty of pictures. She put a medicated foam in his itchy spots twice per day. And chase got plenty of play time and attention. Highly recommend booking with Ashley!”


“We love this woman and her family! They always provide excellent communication and our pup is always a happy tired boy! Elizabeth has kept him countless times and we always feel safe leave our son with her.”

“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.”

“Omar and his partner were awesome! They were super quick to respond, and they took amazing care of Eva. Eva had a blast with their dog, so we'll totally book them again.”

“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.”

“"Brandon has watched my dog, Cookie, three times now, and each time has been fantastic. He consistently provides excellent care, ensuring Cookie is happy and well-taken care of. I couldn't ask for a better dog sitter and highly recommend Brandon for his reliable and professional service!"”

“Ann-Marie took great care of my fur baby while I was out of town. She sent pictures throughout the stay, maintained communication, and was flexible when we pushed our return to a later time. I would definitely recommend her and look forward to hiring her again in the future.”

“I can’t say enough great things about Kamiah! She took such amazing care of my dog, Autumn, and made the whole experience stress free for both of us. Autumn absolutely loves her, and it was clear from the start that Kamiah treats her like family. She kept me updated throughout Autumn’s entire stay with plenty of pictures and videos, which gave me so much peace of mind. It was so reassuring to see how happy and comfortable Autumn was in her care. I highly recommend Kamiah to anyone looking for someone reliable, loving, and attentive to care for their fur babies. She’s truly the best!”

“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.”

“Tonisa was great with our puppy, Dante. She kept in constant communication and put us completely at ease. It’s clear that she cares for the pets you leave with her and that makes you comfortable knowing your little one is just fine while you’re away”

“Our big boy Masai loved staying with Ashley and her beautiful family. They took great care of him. And gave of us photo updates which kept us from wondering about his first overnight stay with someone he'd just met. We will definitely be calling on them again... I can't recommend them enough!”

Over 221 pet parents in Kenwood have booked dog boarding
Kenwood dog parents share their Rover experiences
Bola was a great sitter for my dog Pep. She was flexible, considerate, and communicative with dropoff and pickup, even working with me so my friend could handle pickup logistics. I also appreciate Bola being available over a holiday and sending cute pics of Pep while I was traveling. Thank you!

Elizabeth is great! Bleu clearly had a wonderful time. She can struggle with anxiety and want feeling great but Elizabeth managed all of that and helped make bleu comfortable. I especially appreciated Elizabeth’s love and knowledge of pits which helped me to know she was with someone who understood her and would take great care of her.

Brandon took care of our dog for over a week while our family took a very last minute vacation. He was very responsive and sent videos and pictures. We extended our trip and he was super flexible with that. He also makes sure the Dogs get regular walks outside every day. Really great person to leave your animals with.
We were so lucky to find Ebonee for an extended stay for our dog London. She was incredibly thorough and flexible - we had an intro zoom call (which I LOVED), and she kept us updated with pictures and videos and was understanding of our flight issues returning home. London had a blast and came back to us in great spirits. Thanks for your care, Ebonee!

Stephanie was such a pleasure to work with. She so graciously accepted my last minute request to watch him for 8 days. She was extremely communicative and reassuring that she would give the best care for my senior boy. She went above and beyond for Walle and me. Sent me a ton of pictures and gave him the one on one care that I appreciate. I know my dog fell in love with her. Will definitely be rebooking. ❤️

Danielle was wonderful! I had a last-minute cancelation and needed to find someone to watch my girl for week with only a day and a half notice. Danielle responded very quickly to my inquiry, was understanding and kind, and walked me through my first experience with a dog sitter on Rover. While I was away, she kept me updated with photos and messages frequently enough to put my mind at ease but not so often that it at all interrupted my time away. My girl was happy and healthy when I got back. Would definitely use her again and recommend her to anyone looking!

Phoeying was the best! She was able to accommodate me last minute and took the best care of my girl Luna. She was kind and cared for Luna like it was her own dog. She sent me pictures and updates everyday she was caring for my dog. 100% would book with her again and recommend her services!

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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.
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Dog Boarding FAQs
Frequently asked questions about Rover
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.
















