Dog Boarding in Kenwood, Chicago, IL

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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.

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Sitter Profile Image: Dwight C.
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Dwight C.
Star Sitter
from
$30
per night
5.0 out of 5 stars
210 reviews
85 repeat clients
10 years of experience
Woodlawn, Chicago, IL, 60637

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!

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Lisa G.
Sitter Profile Image: Bola A.
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Bola A.
from
$40
per night
4.9 out of 5 stars
161 reviews
54 repeat clients
15 years of experience
Hyde Park, Chicago, IL, 60615

Bola was awesome! She was attentive to my dog the entire time she had her and was in constant communication with with me! Thank you Bola, you're great!

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David O.
Sitter Profile Image: Yeju K.
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Yeju K.
Star Sitter
from
$50
per night
5.0 out of 5 stars
21 reviews
3 repeat clients
15 years of experience
Loop, Chicago, IL, 60601

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.

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Yvonne Y.
Sitter Profile Image: Timothy B.
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Timothy B.
Star Sitter
from
$39
per night
5.0 out of 5 stars
13 reviews
3 repeat clients
10 years of experience
Lower West Side, Chicago, IL, 60616

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 !

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Michelle C.
Sitter Profile Image: Eric & Eunjin K.
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Eric & Eunjin K.
Star Sitter
from
$55
per night
5.0 out of 5 stars
32 reviews
6 repeat clients
20 years of experience
Near North Side, Chicago, IL, 60611

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!

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Melissa H.
Sitter Profile Image: Rina S.
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Rina S.
from
$35
per night
4.8 out of 5 stars
32 reviews
11 repeat clients
10 years of experience
Woodlawn, Chicago, IL, 60637

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.

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Taylor P.
Sitter Profile Image: Ann V.
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Ann V.
Star Sitter
from
$65
per night
5.0 out of 5 stars
116 reviews
20 repeat clients
2 years of experience
Near South Side, Chicago, IL, 60605

Ann is amazing. She has watched my doggie twice and has been very communicative with us and loving towards him each time. Highly recommend!!!

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Janice J.
Sitter Profile Image: Nathan D.
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Nathan D.
Star Sitter
from
$57
per night
5.0 out of 5 stars
104 reviews
32 repeat clients
22 years of experience
Near North Side, Chicago, IL, 60654

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!

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Shelby H.
Sitter Profile Image: Ashley M.
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Ashley M.
Star Sitter
from
$52
per night
5.0 out of 5 stars
157 reviews
58 repeat clients
10 years of experience
Lower West Side, Chicago, IL, 60608

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!

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Peter W.
Sitter Profile Image: E K.
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E K.
from
$45
per night
5.0 out of 5 stars
345 reviews
165 repeat clients
15 years of experience
Grand Boulevard, Chicago, IL, 60653

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.

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Mya S.
Sitter Profile Image: Tamara J.
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Tamara J.
Star Sitter
from
$55
per night
4.9 out of 5 stars
215 reviews
72 repeat clients
15 years of experience
Grand Boulevard, Chicago, IL, 60653

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.

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Servetta M.
Sitter Profile Image: Omar C.
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Omar C.
Star Sitter
from
$49
per night
4.9 out of 5 stars
40 reviews
17 repeat clients
16 years of experience
Near West Side, Chicago, IL, 60661

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.

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SanziL M.
Sitter Profile Image: Katie M.
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Katie M.
Star Sitter
from
$50
per night
5.0 out of 5 stars
335 reviews
94 repeat clients
15 years of experience
Near North Side, Chicago, IL, 60610

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.

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Daniel G.
Sitter Profile Image: Brandon E.
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Brandon E.
from
$35
per night
5.0 out of 5 stars
16 reviews
10 repeat clients
35 years of experience
South Shore, Chicago, IL, 60649

"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!"

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Donnie S.
Sitter Profile Image: Andre S.
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Andre S.
from
$50
per night
5.0 out of 5 stars
7 reviews
8 years of experience
Loop, Chicago, IL, 60605

Andre took amazing care of Howie during his stay!! Andre and his partner sent me updates and made me feel at ease while I was away! I will definitely recommend Andre to anyone!!

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Nadia S.
Sitter Profile Image: Ann-Marie H.
Verified Enhanced Background Check
Ann-Marie H.
Star Sitter
from
$45
per night
5.0 out of 5 stars
23 reviews
9 repeat clients
4 years of experience
Near South Side, Chicago, IL, 60605

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.

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Era L.
Sitter Profile Image: Kamiah & Casius D.
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Kamiah & Casius D.
Star Sitter
from
$45
per night
5.0 out of 5 stars
26 reviews
15 repeat clients
3 years of experience
Woodlawn, Chicago, IL, 60637

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!

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Tanesha G.
Sitter Profile Image: Daphnay S.
Verified Enhanced Background Check
Daphnay S.
Star Sitter
from
$45
per night
5.0 out of 5 stars
18 reviews
7 repeat clients
14 years of experience
Douglas, Chicago, IL, 60653

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.

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Tiffany S.
Sitter Profile Image: Tonisa J.
Verified Background Check
Tonisa J.
Star Sitter
from
$50
per night
5.0 out of 5 stars
79 reviews
37 repeat clients
15 years of experience
Calumet Heights, chicago, IL, 60617

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

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Avis Lavelle S.
Sitter Profile Image: Ashley B.
Verified Background Check
Ashley B.
Star Sitter
from
$65
per night
5.0 out of 5 stars
124 reviews
56 repeat clients
23 years of experience
Hyde Park, Chicago, IL, 60615

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!

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Lawrence & Simone L.
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Over 221
pet parents in Kenwood have booked dog boarding

Kenwood dog parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Love this sitter!!! Boba comes back better behaved than when he left! He is always so excited to see her, I never have any worries. She is ALWAYS on time and accommodates us when we are early.

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Michelle F.
Boarding
5.0 out of 5 stars

She took great care of my baby during an emergency and sent daily update photos 💕 I felt very comfortable because I was able to tour her home and meet her family beforehand. I definitely recommend!

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Nadia W.
Boarding
5.0 out of 5 stars

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!

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Luella A.
Boarding
5.0 out of 5 stars

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.

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Cyndee L.
Boarding
5.0 out of 5 stars

Kyle did an amazing job taking care of Rika! She kept me updated throughout with photos and messages.

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Ruochen W.
Boarding
5.0 out of 5 stars

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.

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Jennifer P.
Boarding
5.0 out of 5 stars

The best sitter. They provided pictures of my dog during his stay. Took good care of him. I will continue to use their service.

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Marjorie L.
Boarding
5.0 out of 5 stars

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!

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Lauren A.
Boarding
5.0 out of 5 stars

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. ❤️

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Leah F.
Boarding
5.0 out of 5 stars

Moses hooked us up with a last minute Christmas board! He took such good care of our Pete over the holiday, we are so very thankful for him and his family. Would absolutely board with him again :)

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Kelly C.
Boarding
5.0 out of 5 stars

Ashley is excellent! Don’t hesitate to book. We are a repeat customer and highly recommend her. She communicates quickly and takes great care of her dog guests.

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Melissa A.
Boarding
5.0 out of 5 stars

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!

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Margaret M.
Boarding
5.0 out of 5 stars

Cheyanne is wonderful with Woody and has been a huge help, especially with last minute needs. Very communicative and easy to work with!

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James K.
Boarding
5.0 out of 5 stars

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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Karoline A.
Boarding
5.0 out of 5 stars

Dwight is the best. I and my pups actually look forward to their stays. They seem better behaved and sweeter when they return home. If possible, I hope to only book w Dwight in the future.

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Renee H.
Boarding
5.0 out of 5 stars

Pamela was so nice and caring to Mia. She was a life saver on such a short notice. . I know Mia miss here.

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Keisha L.
Boarding
5.0 out of 5 stars

Philip was awesome! It was my first time boarding and I was nervous. He sent videos and pics. Great experience. Already booked again.

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Z H.
Boarding
5.0 out of 5 stars

Agustina was very personable and understood how much Bailey means to me. She updated me with activities and pictures and gave Bailey a home away from home. I am appreciative to her and all she did! I would definitely book with her again!

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Stephen S.
Boarding
5.0 out of 5 stars

Keianna was sooo attentive to my fur baby. She sent photos almost every day and kept me updated on my pup’s health when she had some spotting. Definitely will be booking again!!

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Kamaria P.
Boarding
5.0 out of 5 stars

Tiffany is amazing! Professional, patient, and provide timely updates in reference to your fur babies.

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Shanavia D.
Boarding
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How Rover works

  1. 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. 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. 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

If you’re searching for a Kenwood dog boarding sitter for the first time, visit the sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a sitter before, learn more about how to do this in the Rover app or on your computer.

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.