Pet Sitting & Drop Ins in Oakland, Chicago, IL
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 Oakland pet sitters
“Qutress was great with our shy cat, who even let Qutress pet her which is quite rare for newcomers! She was very communicative and gave us wonderful updates every day. Highly recommend!”

“Just wanted to thank you again for watching rocky and tiger. Leaving them can make us nervous so we appreciate your care of them, it made us feel at ease knowing they were happy 🙂”

“We are the happiest cat parents because we went with Abi. She is reliable and very communicative which is very important to us. We are usually not a nervous people but being new to Chicago and had to leave our cats for a couple a couple of days we were terrified because so far they always traveled with us. Abi made us feel comfortable from the first time that we reached out and I knew that we could count on her to be very communicative. Great experience with Rover. Thank you. Great experience with Abi. We found the person we were looking for. Thank you again. Derek and Irina.”

“I was out of country for 5 days and Evan took good care of my two cats. Litter boxes appeared to have been cleaned regularly and there was plenty of food and water out for the cats.”
“Tamara has been a wonderful support to our family. She’s a quick learner, is patient and communicates well. Our team pups enjoy her and always look forward to their walks with her.”

About: This year, I lost my two rescue dogs within a few months of one another. They came into my life when I was a college kid and left when I entered my first year as a parent. I love my family and friends' furry friends, and life is not the same without them. A dog is not just an animal, but a family member and confidant. From walks, feedings, boarding, and endless cuddles, I can provide any service during lunchtime and weekends as needed. I personally do not enjoy spending my days indoors, so you can expect me to be running along the lake or at the park with my toddler. I work from home, so I can certainly care for animals while working. My son is in school on Mondays, Wednesdays, and Fridays, and I am flexible during my lunch schedule to care for your pup(s). On weekends, I can help with any requests you may have for your special friends. I have a fenced-in yard and a patio deck. I live in a dog-friendly neighborhood with plenty of parks to visit. I can travel to walk your dog for as long as needed, depending on the area.
“Malayna was super awesome. She was flexible with my schedule and gave me great updates on Doc during her visits. She was very communicative and I will definitely be reaching out to her again if I need someone to look after my cat.”

“Madison was absolutely wonderful, I can’t recommend her enough. I have a senior cat with some extra medical needs and she was incredibly patient and kind in taking care of him. I felt at ease knowing my kitty was in good hands with her!”

“Mia was personable and professional from our very first text. After her initial visit, I felt completely comfortable leaving my cat in her hands. I was able to relax while away and come home to a healthy, happy cat!”


About: I am a CPR certified pet sitter who loves animals and loves to care for things. I have no pets of my own because I travel often for my full-time job . However. , I look forward to building a trust worthy, healthy relationship with you and your animal family. I currently work from home full-time so I have flexible hours. I do travel often for work so the further out I know for overnight days is the better. I also am available to walk dogs daily. I live alone and a very nice neighborhood full of lots of trees and families. I keep a very neat and nice home free of anything that could harm animals.
“Jordan was a pleasure to work with. She was so receptive to the needs of our dogs, and was understanding of their character quirks! This was the first time we had drop in visits to our home, and she helped put our nervous dogs at ease. I’d definitely hire her again and recommend her to anyone”

“Great with dogs! Daphne gave our 11yr old and 1yr old so much love and attention during her mid day drop in visits, we are grateful for her service. Wonderful and easy to work with and we will definitely use again.”

“levi you were so amazing!! we looked forward to your updates every day - thank you for taking such great care of cal and santi!! we hate to leave them but it was such a comfort knowing you were around”

About: Hello. My name is Vanessa and I am a huge dog lover. I don’t see dogs as pets but more like family members. I’ve had 10+ years experience dogsiting for some friends dogs ranging from teacup Yorkies to Pitbulls. I have also been a dog owner to Rottweilers, American Eskimos and Shih-tzus. I don’t mind giving references if you need them to verify my work. I am a very sweet energetic and responsible person who promises to care for your dogs as best as I can and give them all my love as if they were my own. I take my responsibilities very serious and promise to follow any guidelines given to me and to keep your dogs safe. I am also willing to care for any other pets you have in the home. Being in the presense of dogs is a wonderful feeling and I will do anything in my power to make them feel comfortable and loved while you are away. If you have any questions feel free to ask. I can’t wait to meet your wonderful furry friends. I work on weekdays but am available to work around your schedule and im off weekends to accommodate any weekend travel you have as well. I am willing to follow any guidelines as far as how you would like your pets taken care of. I want to make sure you are always at ease when you leave your pets with me.
About: Welcome to my care profile! Thanks so much for your consideration. My name is Goddess Jasmine (pronounced Yasmine). 🌻 I am a Muslim & Christ 🌟centered plantbased entrepreneur, author, and content creator from Chicago whose main focus is about reconnecting and interweaving ourselves with nature to cultivate vitality and a cohesive social eco environment in which every being thrives in harmony. I am an enthusiastic world traveler, animal and nature lover committed to sharing joy and my authentic glow everywhere I go. As a seasoned holistic wellness consultant, caregiver, empowerment content creator, and community herbalist I work from home and close to the earth because I love to be outside and nurturing all living creatures. My main personal values center integrity with my inner wisdom, and connecting deeply with all that there is in my environment by sharing love & compassion to every being I encounter. I believe that everyone’s presence is a gift so I take the time to be in gratitude with all living beings I encounter moment by moment. When I was younger I always had a big heart and would care deeply for everyone and everything. I grew up with a guiñea pig, a fish, making friends with trees and babysitting my younger siblings and neighborhood children. I often visited my grandmama’s house to help her play with and care for her German Shepard. As a teenager I attended a rural farming school in Vermont and volunteered on many farms near Boston where I learned how to grow produce and raise livestock namely, cows, ducks, chickens, turkeys, and goats. While In Claremont California, I obtained my BA in Environmental Analysis Africana Studies and a Minor in Studio Art, studying the intrinsic interdependence and the ultimate beauty and creative web connections that support and maintain life. Additionally, I often took care of many of my friends' dogs (chihuahua and other medium mix breeds) while away on extended trips, namely playing with pets, walks, bathing, and poop time. In my 20’s I have had various house sitting opportunities to collect packages and tend for pets, cats, fish and gardens. Currently as a full time dog walker, herbalist and land steward, I feed the local wildlife, tend to an abundant native species garden and perform other domestic duties to maintain the beauty of the home. I believe that we are one with nature so connecting with nature is how we connect with ourselves. Also as an avid world traveler, I look forward to connecting with local animals and plants of any environment. My offering: Providing Premium Care Service Diverse care experiences and utmost dedication to quality care make me the perfect candidate to care for your love one(s) and home. My goal with clients is for us to build a genuine rapport of honesty, trust, and open communication. I am attentive, loving, responsible, nurturing and flexible to fit the needs of everyone I care for. Thanks for your consideration in trusting me in such a sacred opportunity to care for your home, plants, and pets while you're away. I will provide you with the peace of mind and consistent updates to assure you everything is going well at home so you can continue to enjoy your present. What I provide: Safety trust and peace of mind while your away Caring for your all pet needs(play groom, walk, feed) 3 checkin with photos each day Emotional connection with pets Positive Energy I look forward to chatting with you. Messages is the best form of communication for me. Peace ~Goddess Jasmine I currently work virtually as an entrepreneur on part time bases generally less then 10 hrs a week. This give me flexibility and able to sure your needs with the upmost attention. Via consistent messaging, clear communication, reviewing responsibilities and providing updates, I hope to build a genuine rapport of honesty, trust, and open communication with your family 🐶
“Thanks again for over caring for the dogs and stray kitty! My return home to them was like returning from work. (Even tho it was days) They were happy but not overly excited to see me and I know that is nothing short of you giving them the opportunity for their routine to not be disturbed and visiting with them with love!”

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
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 Oakland.
Rover makes it easy to find Oakland 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.



