Dog Boarding in Oakland, Chicago
Find a loving dog sitter to watch your dog overnight at your sitter's home.
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“Susan is very loving and considerate of my pets. One of my dogs wasn’t feeling well and she went above and beyond to make him comfortable. She feels deep compas…” (more)
$50
per night
“Coming from out of town, it is difficult to trust someone with your child. I had the opportunity to meet and inspect Liz house which made us more comfortable. T…” (more)
$40
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 appreci…” (more)
$45
per night
“Andrew is fantastic! At the very last minute my dog sitter fell through, and Andrew came to my rescue. He was available for a meet and greet and was able to wat…” (more)
$45
per night
“Daisy was a wonderful caretaker to our kitten! She kept us updated during his stay and was overall very easy to communicate with. Will definitely be booking aga…” (more)
$45
per night
“Tania took great care of Cookie and went above and beyond to keep her happy while we were gone for 10 days! She got her food, treats and even a new coat! We w…” (more)
$38
per night
“Hands down the best dog sitter we have had in Chicago. Very professional, great service, and loves animals. Honestly just laid back, easy to deal with people …” (more)
$55
per night
“Jamie and Ritz did such excellent an excellent job taking care of my dog Bobbi while I was traveling! They share photos frequently and provide summary of Bobbi’…” (more)
$50
per night
“Judy took amazing care of my senior dog! She was thoughtful, caring, and went the extra mile to help him stay comfy and happy during my time away. I will not he…” (more)
$40
per night
“Jumari was great with our energetic 2-year-old pit mix. And his puppy is sweet as well — the two became fast friends. Jumari was communicative and flexible when…” (more)
$38
per night
“Jasmine took fantastic care of my anxious, senior dog. She is very accommodating, experienced, kind and gentle. Her place is immaculate and neat. I received ma…” (more)
$40
per night
“Kathiuska has been a lifesaver, looking after our dog three times when we had to hit the road. She's super caring and knows how to make dogs feel loved and at h…” (more)
$45
per night
“Holly was amazing! Our dog absolutely loved her and her dog Parker. We appreciated how she made Pippi feel at home, and had great communication with us througho…” (more)
$55
per night
“Monica and Calvin were wonderful! It was our first time leaving Sully for more than a night and their care helped us to relax and enjoy our vacation. We got dai…” (more)
$50
per night
“This was my first time leaving my puppy with someone other than family and Denali enjoyed it. Joye sent me pics everyday and kept me updated about her behavior.…” (more)
$60
per night
“Mayela was a wonderful dog sitter for my greyhound! She send lots of picture and was very easy to communicate with. I would not hesitate to ask her to sit my do…” (more)
$40
per night
“Maria was awesome when we left our older dog with her for five days. She checked in lots each day with texts and photos, which really put us at ease with being …” (more)
$40
per night
“Ashley and her family were fantastic hosts to Chase! We met up beforehand and Ashley was very thoughtful making sure that Chase would be a good fit for them. We…” (more)
$44
per night
“Ericka was very flexible and understanding with our schedule and our dog loves her!” (more)
$40
per night
“Marissa took great care of my husky! I highly recommend her! My husky loved her so much. She took lots of pictures and video to make me feel at ease. Marissa to…” (more)