Pet Sitting & Drop Ins in Oakland, Chicago

“Cassie is amazing at what she does and she is very professional and warm. She took great care of our cat and our home. She was always punctual and always sent wonderful notes and pictures. We would happily choose her again to take care of our cat.”

Sud R.

“I could not be more grateful of Abi taking care of our dogs. I am assured that our fur babies are well taken cared of- especially with Eiko being a senior dog with special needs. She is attentive to their needs and communicates well of any issues that may arise every time.”

NORMA L.

“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.”

Elizabeth & Monica H.

“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!”

Luke M.

“Megan is so attentive and her updates are so cute!! I can tell my kitty was well taken care of and stimulated. This is my first time booking a cat sitter and she was a great one. Would recommend booking with her!”

Zeean F.

“Molly did drop-in visits for my cat Maizie while I was out of town and she was great! Maizie can be shy and anxious with new people and Molly was very patient with her. Molly was also willing to administer Maizie's daily oral medication (and to build the necessary trust with Maizie to do so), which was very important to me. I also appreciated how communicative Molly was and how quickly she responded to questions I had while I was away. I would definitely recommend Molly for cat-sitting/cat care!”

Esther I.

“Thank you!!!”

Annabelle J.

“Laurel has been great with our dog! Rufio was super happy and she was very prompt with visits, great to work with on scheduling, and very friendly! Plus got some super cute pics of the pup during her visits :)”

Crystal C.

“Samantha did an amazing job taking care of my kitties while I was out of town! She sent great pictures and let me know how they were doing each day. Knowing that she was taking great care of them made traveling so much less stressful.”

Katie B.

“Thank you for a great job!”

Jim C.

About: I've had dogs in my life since day one, and have ample experience caring for furry friends, including my neighbors' pups. There's nothing quite like sharing a walk or run with a dog and burning off some energy together – it's where the real bond happens! My part-time work schedule, primarily in the mornings, provides ample flexibility to dedicate quality time to your pet. I'm committed to ensuring your furry friend receives multiple walks daily and feels completely at ease and happy during their stay. I'm also available for consistent communication to keep you updated on their well-being throughout the day. My home offers a secure, fully fenced backyard and a peaceful neighborhood perfect for leisurely dog walks. Plus, I'm just steps away from a dog park for extra energetic playtime! When caring for your pet in your home, I prioritize maintaining their familiar routine and ensuring a safe, comfortable environment by following your specific instructions meticulously. Your pet's well-being and your peace of mind are my top concerns.

“Rebecca was so patient and sweet with our boy. She showed up every visit as promised, left great notes and pictures. This was our first time using a pet sitter and leaving our boy; she made it so much easier on us and reassured us he was doing well. We will without a doubt use her again for our future trips 🤍”

Tristen O.

“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.”

Petia O.

“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”

Lillian & Jason A.

“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!”

Audrey S.

“Cassandra listens and is trustworthy. We spoke for awhile exchanging dog (pet watching) experiences and I knew I could trust her with my dogs and my home: Her visit consisted of having lockbox access to our house, access to the dogs and returning everything as requested.”

Heather B.

“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!”

Kinya M.

“I booked Jasmine VERY last minute and she got back to me quickly and was available for a meet and greet the same day. Everything went off without a hitch while I was gone. Highly recommend.”

Wesley M.

About: Experience potty training, behavioral training, animal lover to the bone. Previous owned a Boston terrier who we lost to cancer also have experience giving dogs medication Currently starting a new business from home all online which allows me to stay home and show your loved one all the attention they deserve Own a house with a big back yard for being in the city, perfect for fetch, sun bathing, or just relaxing. Will do anything in my power to make your loved one feel right at home

About: Welcome to our care profile! Thanks so much for sharing this time with us! My name is Goddess R. I have a priceless travel companion Trust Randle, is my sibling. Together we are a powerful dynamic duo to service all your care needs. Here's more info about us: Goddess R: I am a vegan entrepreneur 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 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 homesitter(cat,fish garden, home upkeep), 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. Trust: Hello Lovelies, my name is Trust. I think all animals and plants are precious and wiser than we might realize. My main job for the last nine years has been lifeguarding and nannying. I've been a pet/house sitter for the last 4 years (so I'm just now making it official). During these last four years I’ve had the pleasure of watching cats, medium to small size dogs, as well as children all in the same day! I am a fast learner and a great communicator. Once I was asked to watch a family friend's older dog so they could fully prepare for a funeral. His name is Kobe. Now Kobe was an older dog and I could tell he really did not like being away from his family. After two days of legit sulking and communication with the family I was finally able to get Kobe to warm up to his new environment. It took more effort and time than I was used to but I was very happy to make Kobe comfortable every which way I could. Furthermore, I believe what I may lack in pet experience I make-up for in caregiving. I have over 10 years of, said experience, bathing small kids, transporting to and from, and taking care of any dietary restrictions. In that time I've learned how to listen to my instincts when watching people's babies, be adaptable, as well as how to take detailed notes in the 1st meet-up or zoom call. I also am very aware and respectful of my environment/surroundings. Which coincidentally leads me to mention my main morals: 1. Treat others how I treat myself, 2. Trust myself and take my time above all else, 3. Live a full life with no regrets. In addition, I spend my free time cooking, taking nature walks, traveling with my besties, reading, writing, and taking care of myself. To Conclude, I value my time, energy, and my joy. So this job checks all the right boxes for me; and any job I take on I give 100% or I don't go for the job at all. Our Teamship; Providing Premium Care Service Our diverse care experiences and utmost dedication to quality care make us the perfect candidates to care for your love one(s) and home. Via video chats, initial home visit, reviewing responsibilities and maintaining consistent contact, we build a genuine rapport of honesty, trust, and open communication with our clients. We are attentive, loving, responsible, nurturing and flexible to fit the needs of everyone we care for. We look forward to bonding with your family and thanks for your consideration in trusting us in such a sacred opportunity to care for your home, plants, and pets while you're away. We 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 trip. What we 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 speaking with over video chat to get to know each other better Peace 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 video chats, initial home visit, reviewing responsibilities and maintaining consistent contact, I hope to build a genuine rapport of honesty, trust, and open communication.