Dog Boarding in Woodlawn, 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.
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Top rated Woodlawn dog boarders
“Bola took great care of my pup child. Rhea received lots of love and was definitely spoiled. (I can tell) lol Bola was responsive and sent updates and videos of Rhea. Rhea really likes Bryce and I hope they become long-term pup friends. I would definitely book again without giving it a second thought.”
“Kamiah and Casius were great sitters for Bailey. For me, it was a very last minute booking and Kamiah was incredibly accommodating to make it work. She was also very quick to contact us on the first day when Bailey wasn't eating (but everything was fine, as this is how Bailey always is at a new place), and Bailey looked very happy in the photos and videos we got each day. Also, Kamiah's pick-up and drop-off were prompt and efficient. I definitely plan to use them again!”
“Definitely would recommend Liz and her family!!!! My last minute sitter to my week long sitter. Always sending updates and taking extra care of my 8 yr old Pittie Maxwell. Maxwell also gives a 5+ review!!!!”
“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!”
“I recently boarded my Pomeranian named Chloe with Linde. Chloe had a wonderful time. I was sent daily pictures and messages. Chloe was well taken care of and Linde is a very nice lady. I will board with her again if the need arises.”
“Emily watched my senior dog, Chloe for 4 days while I was out of town. Chloe is on a ton of meds and is a very anxious girl so I get nervous when I have to leave her. Emily was super communicative and sent lots of pics. She followed directions very well and Chloe seemed to really like her! I highly recommend booking Emily.”
“Katherine did such an amazing job with my pups! They were absolutely loved and cared for. They had such a blast. I almost don’t want to leave this review because I wanna keep her services a hidden gem. She’s the best sitter we’ve had so far!”
“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!! We did a meet and greet first. She was accommodating of any special needs and took care of Rocky like her own! Great with pictures and videos too! Rocky will be back to see Ava, his new friend.”
“My dog is very picky about people, and has no problem being physically or verbally upset when she doesn’t like someone. Therefore, it was very telling that Nas went easily with Beverly upon handing her the leash on her second visit. Beverly is very professional and caring with my dog. She comes highly recommended from a very, very.... very picky puppy and (more reasonable) owner.”
“Katrina is seriously the best!!! Truffles boarded with her over the weekend and she had the best time, cuddling and walking and playing. Katrina sent over multiple (adorably edited and captioned) pictures and videos throughout the day, complete with an end of day report card. I was totally at ease knowing Truffles was getting the best care :)”
“Very happy with Lisette. She responded very quickly and always sent an update everyday with a picture. I will definitely use her in the future! Thanks Lisette for taking good care of my Chewie!”
“Ashley goes above and beyond for pets & their owners- dog parks, long walks, frequent updates, pictures & more! My dog can be a little anxious and he feels so comfortable with Ashley, which is a real testament to her care. Ashley has watched my dog for up to two weeks and it’s a relief to have him in such good hands. We’re so grateful for her services!”
“Yeju was great!! She gave an update each day with pictures and took my pup on plenty of walks. She even baked some dog treats to share when picking up. 10/10 would book again!”
“Tiffany was a fantastic sitter for our dog, Simba. From the initial meet and greet, I felt completely comfortable leaving Simba in her care alongside her sweet dog, Mackenzie. During his two-night stay, Tiffany provided a photo update the first night and a morning check-in, which reassured me that Simba was happy and well cared for. She was always accessible via the app and phone, making communication easy. Tiffany also had no problem with tending to Simba’s eye issue, administering his ointment as needed. I truly appreciate her attentiveness and care, and I would absolutely book with her again.”
“Stacey is simply the best! She took great care of my Golden girl Lucy. Lucy had a ton of fun playing with Stacey's boxer, Joe. I appreciated Stacey's attention to detail, as I don't leave Lucy with just anyone. She also sent super cute videos and pictures while I was away. I look forward to booking future vacays with Stacey, and 10/10 recommend her for watching your pups if you want someone who truly cares for your fur kids!”
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Bola A.Star Sitter
“Bola took great care of my pup child. Rhea received lots of love and was definitely spoiled. (I can tell) lol Bola was responsive and sent updates and videos of Rhea. Rhea really likes Bryce and I hope they become long-term pup friends. I would definitely book again without giving it a second thought.”
Kamiah & Casius D.Star Sitter
“Kamiah and Casius were great sitters for Bailey. For me, it was a very last minute booking and Kamiah was incredibly accommodating to make it work. She was also very quick to contact us on the first day when Bailey wasn't eating (but everything was fine, as this is how Bailey always is at a new place), and Bailey looked very happy in the photos and videos we got each day. Also, Kamiah's pick-up and drop-off were prompt and efficient. I definitely plan to use them again!”
E K.
“Definitely would recommend Liz and her family!!!! My last minute sitter to my week long sitter. Always sending updates and taking extra care of my 8 yr old Pittie Maxwell. Maxwell also gives a 5+ review!!!!”
Dwight C.Star Sitter
“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!”
Tamara J.Star Sitter
“I've left my dog with Tamara 3 times, including an overnight. She's wonderful. She knows how to make my dog comfortable & my dog comes home happy.”
Linde L.Star Sitter
“I recently boarded my Pomeranian named Chloe with Linde. Chloe had a wonderful time. I was sent daily pictures and messages. Chloe was well taken care of and Linde is a very nice lady. I will board with her again if the need arises.”
Emily S.Star Sitter
“Emily watched my senior dog, Chloe for 4 days while I was out of town. Chloe is on a ton of meds and is a very anxious girl so I get nervous when I have to leave her. Emily was super communicative and sent lots of pics. She followed directions very well and Chloe seemed to really like her! I highly recommend booking Emily.”
Katherine C.Star Sitter
“Katherine did such an amazing job with my pups! They were absolutely loved and cared for. They had such a blast. I almost don’t want to leave this review because I wanna keep her services a hidden gem. She’s the best sitter we’ve had so far!”
Ashley B.Star Sitter
“Ashley is very professional, gives great updates about your pup, and takes the job of caring for your pet seriously! 10/10, would strongly recommend.”
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.”
Tonisa J.
“Tonisa was great!! We did a meet and greet first. She was accommodating of any special needs and took care of Rocky like her own! Great with pictures and videos too! Rocky will be back to see Ava, his new friend.”
Beverly B.Star Sitter
“My dog is very picky about people, and has no problem being physically or verbally upset when she doesn’t like someone. Therefore, it was very telling that Nas went easily with Beverly upon handing her the leash on her second visit. Beverly is very professional and caring with my dog. She comes highly recommended from a very, very.... very picky puppy and (more reasonable) owner.”
Hua “Katrina” F.Star Sitter
“Katrina is seriously the best!!! Truffles boarded with her over the weekend and she had the best time, cuddling and walking and playing. Katrina sent over multiple (adorably edited and captioned) pictures and videos throughout the day, complete with an end of day report card. I was totally at ease knowing Truffles was getting the best care :)”
Brandon E.
“Appreciated Brandon taking a last minute request. Philos was well cared for and was very confident when I picked him up. Will definitely be using Brandon again”
Lisette S.Star Sitter
“Very happy with Lisette. She responded very quickly and always sent an update everyday with a picture. I will definitely use her in the future! Thanks Lisette for taking good care of my Chewie!”
Ashley M.Star Sitter
“Ashley goes above and beyond for pets & their owners- dog parks, long walks, frequent updates, pictures & more! My dog can be a little anxious and he feels so comfortable with Ashley, which is a real testament to her care. Ashley has watched my dog for up to two weeks and it’s a relief to have him in such good hands. We’re so grateful for her services!”
Yeju K.
“Yeju was great!! She gave an update each day with pictures and took my pup on plenty of walks. She even baked some dog treats to share when picking up. 10/10 would book again!”
Tiffany O.
“Tiffany was a fantastic sitter for our dog, Simba. From the initial meet and greet, I felt completely comfortable leaving Simba in her care alongside her sweet dog, Mackenzie. During his two-night stay, Tiffany provided a photo update the first night and a morning check-in, which reassured me that Simba was happy and well cared for. She was always accessible via the app and phone, making communication easy. Tiffany also had no problem with tending to Simba’s eye issue, administering his ointment as needed. I truly appreciate her attentiveness and care, and I would absolutely book with her again.”
Kyle H.
“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.”
Stacey R.
“Stacey is simply the best! She took great care of my Golden girl Lucy. Lucy had a ton of fun playing with Stacey's boxer, Joe. I appreciated Stacey's attention to detail, as I don't leave Lucy with just anyone. She also sent super cute videos and pictures while I was away. I look forward to booking future vacays with Stacey, and 10/10 recommend her for watching your pups if you want someone who truly cares for your fur kids!”
Woodlawn dog parents share their Rover experiences
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!
Shantia was very very helpful. I went to check out the space before my vacation and her space was beautiful, lots of room, clean, and accommodating to my dog's needs. I sent very clear and specific instructions for my dog as he is extremely picky and an anxious dog and she took great care of him with no issues on either end. She sent plenty of pictures and videos of my dog while I was away, which eased my anxiety of leaving him with a new person. My dog also does not really vibe well with men and he was able to be around Shantia's boyfriend with no issues or complaints. I will definitely be using Shantia for my dog's care moving forward!
Popular requests near you
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1. Search
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Meet either virtually or in-person with a boarder to discuss the level of care needed for your dogs while you’re away
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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.
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Dog Boarding FAQs
Frequently asked questions about Rover
Only Rover provides comprehensive Woodlawn 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 Woodlawn.
Rover makes it easy to find Woodlawn 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.
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