Pet Sitting & Drop Ins in Woodlawn, Chicago
Book a pet sitter to stop by your home a few times a day to feed and play with your pet.
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Top rated Woodlawn pet sitters
“Abi was the best! She is so caring and went above and beyond. When I asked her to check in with me a couple times while I was gone (8 days) she certainly did, and even sent photos which gave me peace of mind! I came home to very happy cats! I cannot recommend her enough. Thank you Abi!!”
“Samantha was timely, efficient, and took such good care of my kitty while I was away on vacation. Followed directions perfectly and left me with zero worries. She was friendly and kind and clearly loved spending time with my girl. Will absolutely book her again!”
“Kristen makes sure that our senior ladies get their pee breaks. I am certain that our new pup Kaia loves her at their first meeting. Thank yoi for being patient with them!”
“Q went the extra mile to make sure Frank was loved and cared for this summer. Frank obviously grew to enjoy her presence and had a great time while we were away. Q is responsive and always available to answer questions!”
“My cat Kiki is not friendly and will not even stay in a room without anyone new. She let Ms Coretta run he head the first time they met. She is the best!!!”
“Megan was absolutely wonderful! She took fantastic care of my cat and sent check-in photos, played with him each day, and kept my apartment clean. I will definitely come back to her the next time I need a sitter.”
“Malcomn took such great care of my cat, Kashi. He was very communicative and sent updates and photos everyday which I thoroughly appreciated. Kashi and I are so grateful for Malcomn’s service!”
“I lucked out! I had a last minute personal matter, and Kai was quick to let me know what worked best. Papito was happy with his house visit and seemed relaxed. Would happily trust Kai with future drop-in visits.”
“Danielle is a wonderful pet sitter who took superb care of Java while I was away. Last minute, Java was prescribed medicine and Danielle was able to give Java his meds without problem while I was gone. My heart felt at ease with Java in Danielle’s care!”
“Bola’s wonderful! We’re glad to have her support with our dogs.”
About: I’ve grown up with dogs—big and small!—my entire life, and I’ve missed interacting with them since I’ve moved to Illinois. I have extensive experience caring for the pets of family and friends, and pet safety is my #1 priority! I’m currently a student working remotely, so I have time most weekdays and weekends to spend time with your pups and/or take them on walks! I am very conscientious of the environment when handling pets in and out of the home. It’s important to me that pets are secure when on walks or in their home. I’m comfortable crating dogs when desired and double checking any doors, fences, and/or leashes, depending on the setting.
About: Hello! I grew up with my German Shepard mix, Remus, who was my sidekick for 8 years. I now have Anya, a pit mix from Baltimore, who has been my sidekick for 5 years. I have lots of experience walking, giving pets meds, and checking in for food and treats and playtime. I have spent time with and walked loads of different types of dogs. Every dog is unique and I am excited to make friends with yours! I work full time at University of Chicago but keep fairly flexible hours. I can drop in before and after work and check in late at night as well in the Hyde Park area. I can walk your dog and give treats according to your instructions. I can also drop in to give meds or food and let your dog out, depending upon your and your dog’s needs. I am comfortable with small and big dogs.
“Leah was great! She was showed up for feedings exactly when we requested, and her updates and photos let us know that our fur babies were cared for with attention and love! We were able to relax and enjoy our time away knowing they were in great hands.”
About: I grew up with a rescue dog and have always loved animals. Now I live with 3 cats! 1 yr of professional dog experience :) Im a practicing artist, and I take my work with me on the go wherever I am. Currently I can petsit any day of the week, will asjust schedule as needed. I love meeting the client and their pets ahead of time if possible! I always keep a cool head, and I play the animals music. I know they are anxious being away from their owners and just try to reassure them the best I can! I find lots of playtime helps :)
About: I've grown up with dogs of all sizes, had my own for 17 years, and love the joy and energy they bring. Dog sitting and walking is my joy. My dog sitting and walking schedule is flexible, as I work remotely. I can adjust to fit your needs and give your dog the attention they deserve! I prioritize dog safety with a fenced backyard and always ensure a dog-friendly environment, providing your pet with a secure, enjoyable space to play and relax.
“Madeleine was amazing and she took great care of my cat. She also took some engaging photos and it was so nice to see what kitty was up to while we were away. Highly recommend!”
“Dominique did a wonderful job! She was the first sitter I hired for my new pet. Her videos and pictures of my little kitten made me feel a lot better about having to leave. I hope to employ Dominique many times in the future, she makes sure our fur babies are safe and loved.”
“We had a last minute booking with Jordyn. She was great with our pups. We would def use her again.”
“Becca took exceptionally good care of our cat Autumn while my housemate and I were abroad. It had been hard to find good, reliable care (esp. due to some last minute travel plan changes on our part) but Becca stepped right in and everything went smoothly! Becca checked in everyday with updates and info and made sure to ask for tips to help Autumn adjust to having a relative stranger in the house. Thank you again for taking such good care of Autumn and giving is peace of mind while we were away!”
“I can't say enough wonderful things about Peyton as Sheba's pet sitter! Sheba absolutely adored having Peyton around, and it was clear that she enjoyed the company and time spent outside. Peyton went above and beyond to make sure Sheba was well taken care of, offering plenty of love, attention, and outdoor playtime. If you're looking for someone who is reliable, caring, and truly understands pit terriers, I highly recommend Peyton for anyone's pet sitting needs. She’s fantastic!”
Loving pet sitters in your neighborhood
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1. Abi S.
“Abi was the best! She is so caring and went above and beyond. When I asked her to check in with me a couple times while I was gone (8 days) she certainly did, and even sent photos which gave me peace of mind! I came home to very happy cats! I cannot recommend her enough. Thank you Abi!!”
2. Samantha E.
“Samantha was timely, efficient, and took such good care of my kitty while I was away on vacation. Followed directions perfectly and left me with zero worries. She was friendly and kind and clearly loved spending time with my girl. Will absolutely book her again!”
3. Kristen K.
“Kristen makes sure that our senior ladies get their pee breaks. I am certain that our new pup Kaia loves her at their first meeting. Thank yoi for being patient with them!”
4. Qutress T.
“Q went the extra mile to make sure Frank was loved and cared for this summer. Frank obviously grew to enjoy her presence and had a great time while we were away. Q is responsive and always available to answer questions!”
5. Coretta S.
“My cat Kiki is not friendly and will not even stay in a room without anyone new. She let Ms Coretta run he head the first time they met. She is the best!!!”
6. Megan D.
“Megan was absolutely wonderful! She took fantastic care of my cat and sent check-in photos, played with him each day, and kept my apartment clean. I will definitely come back to her the next time I need a sitter.”
7. Malcomn F.
“Malcomn took such great care of my cat, Kashi. He was very communicative and sent updates and photos everyday which I thoroughly appreciated. Kashi and I are so grateful for Malcomn’s service!”
8. Kai H.
“I lucked out! I had a last minute personal matter, and Kai was quick to let me know what worked best. Papito was happy with his house visit and seemed relaxed. Would happily trust Kai with future drop-in visits.”
9. Danielle B.
“Danielle is a wonderful pet sitter who took superb care of Java while I was away. Last minute, Java was prescribed medicine and Danielle was able to give Java his meds without problem while I was gone. My heart felt at ease with Java in Danielle’s care!”
10. Bola A.
“Bola’s wonderful! We’re glad to have her support with our dogs.”
11. Megan T.
About: I’ve grown up with dogs—big and small!—my entire life, and I’ve missed interacting with them since I’ve moved to Illinois. I have extensive experience caring for the pets of family and friends, and pet safety is my #1 priority! I’m currently a student working remotely, so I have time most weekdays and weekends to spend time with your pups and/or take them on walks! I am very conscientious of the environment when handling pets in and out of the home. It’s important to me that pets are secure when on walks or in their home. I’m comfortable crating dogs when desired and double checking any doors, fences, and/or leashes, depending on the setting.
12. Ramanujan S.
About: Hello! I grew up with my German Shepard mix, Remus, who was my sidekick for 8 years. I now have Anya, a pit mix from Baltimore, who has been my sidekick for 5 years. I have lots of experience walking, giving pets meds, and checking in for food and treats and playtime. I have spent time with and walked loads of different types of dogs. Every dog is unique and I am excited to make friends with yours! I work full time at University of Chicago but keep fairly flexible hours. I can drop in before and after work and check in late at night as well in the Hyde Park area. I can walk your dog and give treats according to your instructions. I can also drop in to give meds or food and let your dog out, depending upon your and your dog’s needs. I am comfortable with small and big dogs.
13. Leah C.
“Leah was great! She was showed up for feedings exactly when we requested, and her updates and photos let us know that our fur babies were cared for with attention and love! We were able to relax and enjoy our time away knowing they were in great hands.”
14. Sol S.
“Sol was truly so wonderful with our dog, Pony, and came through for us in a big way with a last-minute request (for *four* days of sitting!) Also I think it's worth noting that when we returned, Pony was noticeably better behaved on his leash for walks. Pony's pretty big (85 lbs!) and can be rambunctious, but it was so clear from the get-go that Sol had everything totally under control. He came to us highly recommended by another dog/house sitter we love, and now that we've been able to work together, I would recommend him to anyone!”
15. Sarah E.
“Sarah is always great with my Shiba Inu. She takes him on long walks, consistently plays with him, feeds him on time, and even brushes him. Her communication style is perfect. 10/10 would recommend.”
16. Madeleine F.
“Madeleine was amazing and she took great care of my cat. She also took some engaging photos and it was so nice to see what kitty was up to while we were away. Highly recommend!”
17. Dominique F.
“Dominique did a wonderful job! She was the first sitter I hired for my new pet. Her videos and pictures of my little kitten made me feel a lot better about having to leave. I hope to employ Dominique many times in the future, she makes sure our fur babies are safe and loved.”
18. Jordyn W.
“We had a last minute booking with Jordyn. She was great with our pups. We would def use her again.”
19. Rebecca B.
“Becca took exceptionally good care of our cat Autumn while my housemate and I were abroad. It had been hard to find good, reliable care (esp. due to some last minute travel plan changes on our part) but Becca stepped right in and everything went smoothly! Becca checked in everyday with updates and info and made sure to ask for tips to help Autumn adjust to having a relative stranger in the house. Thank you again for taking such good care of Autumn and giving is peace of mind while we were away!”
20. Peyton W.
“I can't say enough wonderful things about Peyton as Sheba's pet sitter! Sheba absolutely adored having Peyton around, and it was clear that she enjoyed the company and time spent outside. Peyton went above and beyond to make sure Sheba was well taken care of, offering plenty of love, attention, and outdoor playtime. If you're looking for someone who is reliable, caring, and truly understands pit terriers, I highly recommend Peyton for anyone's pet sitting needs. She’s fantastic!”
How Rover works
1. Search
Read verified reviews by pet parents like you and choose a 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 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!
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 pet 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.
Pet Sitting FAQs
Frequently asked questions about Rover
Pet sitters on Rover are free to set their rates. The median cost to hire a pet sitter in Woodlawn on Rover as of Jul 2024 was about $20 per night, after factoring in Rover’s service fees. A pet sitter’s rate may also change as you customize your booking to fit your and your pet’s needs.
As of Jul 2024, there are 1,288 pet sitters in Woodlawn. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, pet sitters joining Rover must pass a background check for you and your pet’s safety.
Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, 85% of Woodlawn pet sitters respond in under an hour.
Pet sitters in Woodlawn have an average of 13 years of experience. Pet sitters with repeat customers have an average of 6 repeat clients. Experience can vary from pet sitter to pet sitter, but you can view reviews, years of experience, and number of repeat clients when you compare pet sitters in Woodlawn.
Rover makes it easy to find Woodlawn pet sitters to provide loving care from their own home. The background-checked, 5-star pet sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet sitting is great for:
- Pets of all ages and abilities, including puppies
- Pet parents looking for a safe, loving alternative to a kennel
- Pets who’d love to socialize with their pet sitter’s pets
There are 1,288 pet sitters in Woodlawn on Rover, so you’re sure to find the perfect match for your pet! In Woodlawn, 94% of pet sitters offer daily exercise, 90% offer medication administration, and 87% have experience with senior pets and pets with special needs. We know each pet is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, pet sitters joining Rover must pass background checks for you and your pet’s safety.
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your pet sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your pet 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 pet 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 pet 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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