Pet Sitting & Drop Ins In Jackson Park
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 Jackson Park pet sitters
“Leandrea was terrific. She came over to meet the cats before I left, she sent pictures and updates daily, and I came home to two very happy cats and clean litter boxes. Couldn't have asked for better. Thanks so much!”
“Sarah has become part of our family. She's an awesome communicator and is so good with my dog who has anxiety issues among other things. He just loves her, and she makes him feel safe and happy. On her own she introduced him to doggy puzzles which I hadn't thought of.”
“Vanessa was amazing! She followed all the instructions to perfection. She was super sweet caring and loving with our pups, you can clearly see they like her. She was super responsable and always arrived on time! Definitely will book again! 100% recommended!”
About: My unconditional love for all animals. Every cat or dog that I meet I treat and cherish as if they were my own fur baby. I do work a full time job, 8-4 Mon-Fri. However, I am looking to use some of my free time taking care of your fur baby! I do my best to maintain whatever routine you have with your fur baby. I am willing to go the extra mile to make your pup feel safe and comfortable while you are away.
About: Hi, I’m Ashling! Animals have been a central part of my life for as long as I can remember. I grew up with a Soft Coated Wheaten Terrier, spent my teenage years as the go-to neighborhood babysitter and pet sitter, and today, I’m a proud pet parent to two wonderful Wheatens of my own. Because of my personal experience with dogs of all backgrounds, I understand that every animal is unique. My philosophy is to always meet animals where they are at—building trust at their pace while providing a safe, confident, and structured environment. I'm currently accepting weekday appointments for now and will accept some overnights and weekends. I have a flexible schedule at this point and will be able to care for pets multiple times throughout the day and night. I will treat your home and your pets with the utmost respect and try to follow the schedule and routine to make sure your pet is comfortable in their home while you're away. Their safety and comfort is my highest priority.
About: Growing up, I always had a pet. Animals are no stranger to me and I am quite fond to any pet. They are life’s companionships. I’m currently working part- time so I’m mostly available on my weekends or Monday and Wednesday after 6:30. But I do have some free time in between other week days - all depends on school as well. I give pets space for them to adjust new company. Then slowly be able to come in contact and hopefully be able to earn their trust.
About: I’m a true dog lover who treats every pup like family. I provide a safe, loving, and dependable environment where your dog will receive plenty of attention, affection, walks, and playtime. I understand how important routines and trust are, and I’ll always keep you updated with photos and messages so you can feel confident your furry family member is happy and well cared for. I look forward to meeting you and your pup! I am currently at home all day not working and have plenty of time to take care of your pet and be attentive to their needs. I have a fenced in yard to keep your dog safe and secure. I can also keep your dog in a crate or behind a gate if needed.
“Michele was great with Pekoe. His photos showed my stranger-averae parrot to be calm and happy. She did a great job respecting his space and personality while keeping his bedtime routine intact. I've already booked her for my next 2 trips. 🙂”
About: Hello! (Usually available after 5:30 pm during the week days and free on Fridays) My name is Stephane and I'm a project engineer in environmental science. I have had cats since my childhood, a mother, and a daughter I had the chance to live with for 20 years. Today, I have a cat I got from a refuge, called Juno. He was super shy and introverted due to his sad past but I can see a lot of progress in his behavior. He is some work but seeing him getting more and more free makes me happy. I have also always been with dogs and love to take them on walks and play with them. I took care daily of my roommate's dog (Kenny) in Toronto, taking him regularly on walks and dog parks. I live in North Water Street and can drive to your home to take care of your best friend(s). I'm also an aquarist and can look of your aquatic friends if you need it. I hope to see you soon and your best friend! I always start my day with a hello to Juno :) He usually comes to me claiming food like for having breakfast and we cuddle after. Which is a perfect start for having a good day. I will follow any instructions you give me to keep your pet routine as normal as possible. I will be respectful of your space and will always ensure that everything is closed and safe for your pet. I can send you updates with photos if you need them.
“We dont typically leave our cats for more than a few days/nights so i was anxious about leaving them for a full two weeks but i felt so comfortable knowing Angela was taking care of them! I came back to happy and healthy cats. couldn’t have asked for more :)”
“Great work taking care of my kitty!! Followed instructions and provided updates, photos etc. Also rearranged the drop-in to get a visit in before a snow storm. A++!!!”
“Marilia did a great job cat sitting. Marilia is responsive, caring, and will go above and beyond to take care of your pet/home while you’re away. Definitely would rebook.”
“My dog Miley is very people selective, and Courtney is wonderful with her! Courtney is super attentive to Miley’s needs and I always feel so comfortable knowing Courtney is taking care of her.”
“Courtney was absolutely wonderful! She watched my cat Blue while I was gone and sent loads of adorable pictures and videos daily and kept me updated on how Blue was doing. She took the extra time to play with him and brush him, and handled giving him his ear drops and medication fantastically!! I definitely recommend Courtney and look forward to continuing to work with her for all my pet sitting needs :)”
“Kristine was awesome with my cat Winnie. She can get scared with new faces but Kristine was kind and gentle with her. 10/10 would book with her again!”
“Lilly was amazing with our two cats while we were gone for a week! Both of our girls absolutely loved her (even our shy kitty) and warmed up to her instantly. She is very communicative and goes above and beyond. Do yourself a favor and hire her! ?”
“Liz really went above and beyond with my boys! She spent an lot of time making sure they had playtime, that my apartment was a comfortable temp for them, and checked in regularly to see if I needed her to do anything else around my house. I would have her care for any pet I have without reservation.”
About: I’ve been a devoted animal lover and pet owner for as long as I can remember. From dogs and cats to caring for pets with unique personalities and needs, animals have always been a huge part of my life. Currently, I share my home with a lovable, mischievous hound mix who keeps me on my toes and a cat who completely stole my heart. A few years ago, I lost my soul dog, Jersey, and that experience deepened my understanding of the special bond we share with our pets. I know firsthand how difficult it can be to leave them behind and trust someone else with their care. That’s why I treat every pet as if they were my own—with patience, affection, attention, and plenty of love. Whether your pet needs a quick drop-in visit, playtime, cuddles, a walk, or simply a friendly face while you’re away, my goal is to make them feel safe, happy, and cared for. I also know how important peace of mind is for pet parents, so you can expect regular updates, photos, and communication throughout my visits. Because I work from home, I have a flexible schedule that often allows me to accommodate drop-in visits and pet care needs throughout the day. I’m committed to providing dependable, compassionate care and building a trusting relationship with both you and your pets. I look forward to meeting your furry family members and becoming someone you can count on whenever you need a helping hand! 🐾❤️ I work from home and have a decently flexible schedule. I have a young son and pets of my own but thankfully I share these responsibilities with my rockstar husband so I will be able to care for your fur babies. I understand that having a stranger in your home can be a little uncomfortable. I will 💯 respect your space and keep things clean in order for your while you are gone. Please let me know your preferences for my stay.
Over 6 pet parents in Jackson Park have booked pet sitting
Jackson Park pet parents share their Rover experiences
Mallory is just the best honestly. My dog is my world and it was very difficult to go up north this year without her. There was so much incredible communication and photos with visit summary’s that made my heart melt. My elderly cat had a few accidents and without thought she cleaned it up and kept everyone loved while I was away. I would use her again in a heartbeat. I understand why she is a star sitter. She is extremely trustworthy with the lives and routines of your pets. <3
Liz is so sweet & follows directions very well! Our two boys absolutely love her as she goes above and beyond to make sure they are taken care of while we are out of town. I was so happy Liz was available to watch them as she knows their routine and always willing to help more if needed. Cannot recommend enough!
Caitlyn is an amazing cat sitter! I hired her while I was away for a work trip and she dropped in multiple times a day and medicated one of my cats (who gets several meds throughout the day). On top of that, her updates were phenomenal! She gave me up descriptions of my cats activities that were very consistent with their personalities, so I could tell she was really paying attention to their moods and needs. One of the best cat sitters on here and I would easily hire her again! So flexible to work with, sends amazing photos, and responds quickly.
Nicole was excellent! When she came for the meet and greet, she asked excellent questions to really get to know our girls and set expectations. She was calm and let our girls come to her. Then, when she came for the visit, she took excellent care of our kitties and was able to pill our calico successfully! Throughout the whole experience she communicated super well, which is something that we value. We will absolutely recommend and rebook!! Thanks Nicole!
This is our second time booking with Emily, and we’ve loved her so much that we’ve referred friends to her who confirm the same sentiment: She is just fantastic at what she does. Her experience with young children as an elementary school teacher certainly translates to being phenomenal with furry friends! We were concerned that our shy calico would hide, but she was happily making friends within a few visits. Rover reports were detailed (and so sweet!) each day. Cannot continue recommending Emily enough!
Popular requests near you
Select a filter and find qualifying Jackson Park sitters!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!
The median cost per night for pet sitting in Jackson Park is $20
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 Jackson Park on Rover as of Jun 2026 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.
Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, pet sitters on Rover respond in under an hour.
Experience can vary widely from pet sitter to pet sitter, but you can view reviews, years of experience, and number of repeat clients when comparing pet sitters available in Jackson Park.
Rover makes it easy to find Jackson Park 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
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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