House Sitting in Woodlawn, Chicago, IL
Find a loving house sitter to watch over your pets and your home.
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Top rated Woodlawn house sitters
“Jayden is an excellent pet sitter and communicator. I loved the updates, photos and videos. They stayed overnight and took care of 4 needy cats. I highly recommend!”
“Bre was fantastic watching our Cat! He has some medical that require extra effort/ needs and Bre followed directions and was very communicative in times of doubt. She also took great care of our house. We will hire her again and highly recommend her to watch your pets!”
“Ava was wonderful with our 3 pups. She knew how to manage their chaos and treated them so sweetly. She left the place looking great and really just went above and beyond. We will definitely be using her services again.”
“Laurel was AMAZING!!! Our dogs had the best care and we received updates and pictures the whole time we were gone! We feel so lucky to have found Laurel and would love to have her dog sit again in the future! :)”
“I can’t thank Brianna enough for the amazing care she gave to both my pup Gigi and my home while I was out of the country. From our initial meet and greet, Brianna was sweet, pleasant, and radiated an aura of calm and kindness that instantly put me at ease. I just knew Gigi would be in safe, loving hands—and I was absolutely right. Throughout my time away, Brianna kept me fully updated with all the photos and videos I requested, which gave me so much comfort. It truly warmed my heart to see how well Gigi was being loved and cared for. Brianna went above and beyond, not only with Gigi but with my apartment as well—everything was left clean and tidy, which I so appreciated. Brianna, thank you for treating my baby like your own. You’re truly one of the best out there, and I’m already looking forward to booking you again the next time I’m away!”
“Anais is the best!! My boyfriend and I went on our first long trip away from our puppy, Anais sent lots of pictures and videos every day. She was very responsible and responsive to our texts. In addition to taking great care of our puppy, she cleaned our entire apartment! Definitely recommend and will be rebooking in the future!”
“Jordan is a delight - amazing communication & very responsive from 1st request! She's a true animal Lover & have such good care to our Scoutie! Daily walks, loads of attention & affection - with photo updates each morning & evening! She will be our go to sitter from now on. We're thrilled to have found her!!”
“Nicole R. spent 4 days with Sunny and Sunny LOVED her! My house was spotless when I returned and I will definitely book her in the future. (Am working on that happening really soon.). I definitely would recommend her.”
“Alexa was a very thoughtful, thorough, and kind sitter. She followed all the house rules and Nala rules. She left our home better than when we came back. We will definitely hire her again.”
“Elizabeth took amazing care of our dog and our home while we were away for a wedding this weekend. She is a great communicator, updated us every day on how our dog was doing, and our dog was in great spirits when we returned! We will definitely ask her to watch our dog again in the future and would highly recommend to a friend.”
About: I'd love to meet your dog or cat and you can trust I'll treat them like my own. I know how to keep them safe and happy while you're away. I'll send you a good photo too my camera roll is mostly all photos of dogs. Please do not hire me if you crate your dog, I won't do that. I work freelance so my availability is flexible. I prefer we conduct a meet and greet first, to make sure your pet is comfortable with our plans! Walks and care provided in clients home only, I can't provide boarding. I will be sure we establish comfort in our meet and greet, please be sure to provide vet information in case of any unexpected emergency.
“Daniela did a great job. She was very loving to my dogs and I appreciated that she spent so much time with them. She also left my house very clean! She really had a bond with them and I can tell she really loves animals.”
“My Dog Dottie loved Ava! Dottie has tons of energy and Ava spoiled her with long walks and lots of dog park trips. I felt so relieved that my pup was in great hands. Ava sent lots of pictures and updates and left the house nicer than she found it. The best! Already booking her again”
“Shakira was absolutely amazing, not only did she take great care of my lil fur baby but she sent plenty of photos and her communication was great. I will hopefully use Shakira anytime I need a sitter. If your thinking about booking Shakira as a sitter DO IT !!!!!”
“Samantha was marvelous! I’m always nervous leaving my 9yo wheaten terrier, as she’s been known to get kind of cranky and snarly around other dogs. However, Samantha assured me she felt comfortable with my high-maintenance fuzzy friend. She sent regular photos and updates throughout my week-long trip, and always responded quickly whenever I’d reach out. My place was very clean when I returned and, most importantly, my dog seemed happy and relaxed. I’ll definitely reach out to Samantha again for upcoming trips!”
“We had the best experience with Carlie! Her and Ani (her pup) stayed at our house for the week while we were on a family trip. Our boy Leo is a Great Dane and she was amazing with him. Not everyone can handle big dogs. I felt at ease with Carlie at our home. I got frequent updates and pictures too! The house was well maintained and in the condition we left it in. 5+ ⭐⭐⭐⭐⭐✨”
About: I have taken care of dogs my entire life , I was a baby who grew up with a Irish Setter. and so my life's journey has been traveled with My best buddies . My family and my pets. Their love and kindness cannot be measured and they deserve the very best of care. I pride myself on training tips and methods i have used on puppies to older dogs i’ve taught behavior adjustments. I believe a healthy fit pup is a happy one . I was also involved in a program we called visiting buddies , taking puppies to spend time with senior citizens and pre school students. throughly enjoyed by everyone involved. I am currently working part time and my schedule is flexible, I work in events. my availability is after 12 for walking and boarding generally but with enough notice I can work some morning hours. I have a large fenced yard as well as a dog run on the side of our home. I have a very friendly furry baby who will give your pup hours of entertainment. I you. would prefer. your pup was crated I. have a very large kennel indoors as well as outside. My home has tons of space .
“Christopher was great! He house sat for over 2 weeks and took care of our elderly cat, who needed meds twice a day and regular infusions. We got regular photos and updates and returned to a tidy home and a happy old cat. Would definitely recommend Christopher to others!”
Loving house sitters in your neighborhood
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Jayden Phoenix (They/Them) P.Star Sitter
“Jayden is an excellent pet sitter and communicator. I loved the updates, photos and videos. They stayed overnight and took care of 4 needy cats. I highly recommend!”
Brianna J.Star Sitter
“Bre was fantastic watching our Cat! He has some medical that require extra effort/ needs and Bre followed directions and was very communicative in times of doubt. She also took great care of our house. We will hire her again and highly recommend her to watch your pets!”
Ava M.Star Sitter
“Ava was wonderful with our 3 pups. She knew how to manage their chaos and treated them so sweetly. She left the place looking great and really just went above and beyond. We will definitely be using her services again.”
Laurel M.Star Sitter
“Laurel was AMAZING!!! Our dogs had the best care and we received updates and pictures the whole time we were gone! We feel so lucky to have found Laurel and would love to have her dog sit again in the future! :)”
Brianna S.
“I can’t thank Brianna enough for the amazing care she gave to both my pup Gigi and my home while I was out of the country. From our initial meet and greet, Brianna was sweet, pleasant, and radiated an aura of calm and kindness that instantly put me at ease. I just knew Gigi would be in safe, loving hands—and I was absolutely right. Throughout my time away, Brianna kept me fully updated with all the photos and videos I requested, which gave me so much comfort. It truly warmed my heart to see how well Gigi was being loved and cared for. Brianna went above and beyond, not only with Gigi but with my apartment as well—everything was left clean and tidy, which I so appreciated. Brianna, thank you for treating my baby like your own. You’re truly one of the best out there, and I’m already looking forward to booking you again the next time I’m away!”
Anais T.
“Anais is the best!! My boyfriend and I went on our first long trip away from our puppy, Anais sent lots of pictures and videos every day. She was very responsible and responsive to our texts. In addition to taking great care of our puppy, she cleaned our entire apartment! Definitely recommend and will be rebooking in the future!”
Jordan W.
“Jordan is a delight - amazing communication & very responsive from 1st request! She's a true animal Lover & have such good care to our Scoutie! Daily walks, loads of attention & affection - with photo updates each morning & evening! She will be our go to sitter from now on. We're thrilled to have found her!!”
Nicole R.
“Nicole R. spent 4 days with Sunny and Sunny LOVED her! My house was spotless when I returned and I will definitely book her in the future. (Am working on that happening really soon.). I definitely would recommend her.”
Alexa B.Star Sitter
“Alexa was a very thoughtful, thorough, and kind sitter. She followed all the house rules and Nala rules. She left our home better than when we came back. We will definitely hire her again.”
Elizabeth D.
“Elizabeth took amazing care of our dog and our home while we were away for a wedding this weekend. She is a great communicator, updated us every day on how our dog was doing, and our dog was in great spirits when we returned! We will definitely ask her to watch our dog again in the future and would highly recommend to a friend.”
Jennifer D.
“I’ve known Jennifer for nearly thirty years. She has always had pets since I’ve known her, and she has always been a loving caregiver to them. I would absolutely recommend her as a responsible caretaker for your pets.”
Abi S.Star Sitter
“Abi was great with our pups! They were calm and happy when we got back from our trip, and the house was in great shape. Looking forward to the next time.”
Daniela M.
“Daniela did a great job. She was very loving to my dogs and I appreciated that she spent so much time with them. She also left my house very clean! She really had a bond with them and I can tell she really loves animals.”
Ava A.Star Sitter
“My Dog Dottie loved Ava! Dottie has tons of energy and Ava spoiled her with long walks and lots of dog park trips. I felt so relieved that my pup was in great hands. Ava sent lots of pictures and updates and left the house nicer than she found it. The best! Already booking her again”
Shakira C.
“Shakira was absolutely amazing, not only did she take great care of my lil fur baby but she sent plenty of photos and her communication was great. I will hopefully use Shakira anytime I need a sitter. If your thinking about booking Shakira as a sitter DO IT !!!!!”
Samantha E.Star Sitter
“Samantha was marvelous! I’m always nervous leaving my 9yo wheaten terrier, as she’s been known to get kind of cranky and snarly around other dogs. However, Samantha assured me she felt comfortable with my high-maintenance fuzzy friend. She sent regular photos and updates throughout my week-long trip, and always responded quickly whenever I’d reach out. My place was very clean when I returned and, most importantly, my dog seemed happy and relaxed. I’ll definitely reach out to Samantha again for upcoming trips!”
Luwam Z.Star Sitter
“Great communication, excellent attention to detail! My dog was safe and happy with Lu”
Carlie R.
“We had the best experience with Carlie! Her and Ani (her pup) stayed at our house for the week while we were on a family trip. Our boy Leo is a Great Dane and she was amazing with him. Not everyone can handle big dogs. I felt at ease with Carlie at our home. I got frequent updates and pictures too! The house was well maintained and in the condition we left it in. 5+ ⭐⭐⭐⭐⭐✨”
Monique O.
“What can I saw about this amazing Dog Lover!!! Madam Monique has secured and managed my dogs for over 20 years. Her compassion for animals is unmatched and should be respected and appreciated within the community of Dog Lovers!”
Christopher C.
“Christopher was great! He house sat for over 2 weeks and took care of our elderly cat, who needed meds twice a day and regular infusions. We got regular photos and updates and returned to a tidy home and a happy old cat. Would definitely recommend Christopher to others!”
Woodlawn pet parents share their Rover experiences
Samantha has walked our dog several times before but this was our first time having her house sit to take care of our dog and cat while we were on vacation - she did an incredible job! Clear communication, regular updates and left our place clean. Would love to have her back :)
Monica was amazing with my kitten Stormie while we were away for the weekend. She responded very quickly and was able to arrange a meet and greet with us under short notice as well. I got update pictures and videos over the course of the weekend, so I always knew my baby was in good hands. She also left our apartment in perfect condition (which you can imagine is not easy with a kitten). I would 1,000% recommend Monica for any pet sitting as she definitely took the stress out of the whole weekend ♥
Brianna is so amazing, would 100% recommend her to take care of your pet! She is so kind and asked many great questions about our pet and home at our meet and greet. She took care of our dog for over two weeks and sent daily pictures and updates. She played with him, took him on long walks and brushed him. Our dog clearly loved her and her communication made us feel so reassured on our trip! She also left our place very clean. We are so lucky to have found her!
Laurel was SO great to my pup!! My dog can be a bit anxious around new people, but she warmed right up to Laurel and it made my trip away a breeze. I was super impressed by her frequent updates, and just going above and beyond to make my pup feel cared about. 10000/10 recommend Laurel!
Alexis took such wonderful care of our two young cats over the holiday weekend, my fiancé and I were truly impressed. She was highly respectful of our home, and our feisty shorthand got more snuggly with her than she typically does with at least one of her parents! I would recommend Alexis to any cat parent and we'll certainly look to book her for our next petsitting need.
Staci was amazing with our animals during our recent 9 day vacation. She stayed nights at our house to take care of our two cats and our energetic dog. She took wonderful care of them and was able to get our elderly cat to eat and take her pills. We highly recommend using Staci to care for your cats or dogs!
Henry watched our girls and home for 2 weeks while we were out of the country. The girls loved spending time with him and Henry sent us regular updates throughout our trip. He instantly bonded with our pups on a previous trip and the girls were super excited to see him. When we returned the pups were happy, well cared for, and the house was clean/organized. It is great to know that we are leaving the girls in good hands and I’m sure the pups are looking forward to the next time they get to see Henry!
Viola made us feel so comfortable and at ease with her care for Champ AND our home. She is an inherent pet lover and nurturer and she makes sure she goes above and beyond to make both you and your pet feel safe. She even cleaned up the apartment before leaving without us even asking! We will definitely be asking her back to watch our “son”.
This was our first time working with Vanessa and there were a few kinks to work out over text during her stay (getting into our apartment/timing, communication and check-in frequency) but after day 1 it was super smooth! She sent great pictures of our pets (a cat and dog) and they clearly enjoyed having her there with them. It was nice for us to know they had someone caring for them when we were gone! Our apartment was also clean and organized when we got back.
How Rover works
1. Search
Read verified reviews and choose a house sitter who’s a great match for you and your pets
2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets 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!
The median cost per night for house sitting in Woodlawn is $50
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 house sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
House Sitting FAQs
Frequently asked questions about Rover
House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Woodlawn on Rover as of Aug 2025 was about $50 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.
Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 92% of Woodlawn house sitters respond in under an hour.
Experience can vary widely from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when comparing house sitters available in Woodlawn.
Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Woodlawn house sitters are great for:
- Dogs who’d prefer to stay on their home turf
- Cats and caged pets
- Pet parents on a tight schedule
- Keeping an eye on your home and plants while you’re away
Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house 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 house 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 house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.
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