Pet Sitting & Drop Ins in Grand Boulevard, Chicago, IL

“Brianna is simply the best! We’re so lucky we met her and for all the great care she’s given our pup, Bear, throughout 2025. This most recent stay was no exception. She is always on time, provides great communication (& updates!), and, of course, is so kind and patient with Bear. You’re making the right choice working with her!”

David P.

“It was my first time using rover and I was looking for someone who truly understands dogs, and its Tamara! Tamara was a true blessing while I was away in Mexico. My dog isn’t usually quick to trust—he even tried to bite her when they first met—but she was so patient and kind with him. By the end of the week, he was waiting at the door for her, tail wagging, 30 minutes early. I could tell he really bonded with her. I’m so grateful and would absolutely have her watch him again.”

Al T.

“Evan is responsive and responsible. He kept me up to date on my cats' progress and is pleasant to work with.”

Yolaine D.

“Lynettra is an exceptionally kind and loving cat sitter. She made sure our Brinkis had enough play time and nourishing food. She even got him a Christmas present while we were away! I would highly recommend her!”

Joanna A.

“I am always very nervous when I leave my furry girl alone. It was the first time we booked Qutress and she did it amazing. On a couple days did a great bond and my Kira is always scared to everyone, she really had the touch, the care and patience for her. Qutress is reliable, careful with all details and kind. I would repeat her service as much I need it.”

Carmen C.

“Daphne was amazing with our fur babies and gave them all the love while we were gone. She was as punctual, professional and caring. She was as excellent with communication and follow up. We will use her service again knowing the dogs are taken care of.”

Petia O.

“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.

“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.

“Jordan did great! Went above every way!”

Brendon A.

“Christina is a very considerate and communicative pet sitter!”

Lucas H.

“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!”

Heather B.

“Great! No complaints. Will be scheduling again soon. My cats loved her and she followed instructions exactly.”

Chevonne C.

About: Although my aspiration to be a vet was cut short because I was too emotional, my love for animals never faded! Throughout my life I’ve cared for dogs, cats, gerbils, hamsters, and hermit crabs, and I’m happy to say that all of them lived happy lives under my care. These experiences have helped me become adaptable and attentive to different care styles. My goal is to provide consistent, loving care so your pet feels safe, exercised, and well cared for while you’re away. I work a full-time hybrid job that offers the flexibility to attend to responsibilities as needed. This allows me to consistently care for my own cat’s daily needs and ensures I can provide the same attentive, reliable care to your pets as well. I have one cat in my home, and a decent amount of space for your pet to explore and relax. There is not a concern for them escaping, as I live in a condo building and my windows can only be opened from high up, and my balcony stays closed unless I’m cleaning. I also have space for a crate if needed.

About: I have 7 years of professional pet care experience alongside growing up taking care of pets. I have always felt a special connection with animals which carries into my pet care. With every animal I meet I prioritize developing a bond with them so they feel safe and enjoy our time together. I have experience with training puppies, leash training, and administering medication. My attention to detail and empathy prove me to be an advantageous caretaker. I will be sure not to miss any details with care instructions and will give your pup just as much love as I do mine. I understand leaving the care of your furbaby in someone else's hands can be stressful, but with me, you can trust your furbaby will be well taken care of. I currently work part-time with a very flexible schedule that changes weekly, so I have plenty of time for your pup! I have availability almost every day. I make sure to review all care instructions before entering the home. I always allow myself to get acquainted with the dog first then continue with service.

“Malayna did a great job checking in on my 2 kitties! She was very kind and patient with one of them who was a bit afraid. Special feeding requirements for my older kitty were also handled well!”

Sue W.

About: As a dedicated and passionate pet sitter, I take pride in offering more than just a place for your pet to stay—I provide them with a loving, safe, and stimulating environment. What sets me apart from other sitters is my ability to care for pets of all ages and needs, including training puppies and providing special attention to senior pets. I specialize in: Puppy Training: I help puppies develop good habits early, offering positive reinforcement techniques to ensure they grow up well-behaved and confident. Senior Pet Care: I understand the unique needs of older pets, offering gentle care, medication administration, and extra comfort to ensure they remain happy and healthy in their golden years. Flexible and Personalized Care: Whether your pet needs daily walks, companionship, or special attention, I tailor my services to meet their individual needs. Rest assured, your pet will be treated with the same love and care I would give my own, providing you peace of mind while you're away. Pet care is an integral part of my daily routine. I prioritize flexibility and consistency to ensure that your pet feels comfortable and well cared for. Here’s how I incorporate pet sitting into my schedule: Daily Care: I am available for drop-in visits, walks, and playtime throughout the day, making sure your pet stays active and engaged. My schedule allows me to spend quality one-on-one time with pets to meet their exercise, companionship, and care needs. Flexible Hours: Whether you need morning, midday, or evening care, I adjust my schedule to ensure your pet gets the attention they need, especially if they’re on a routine or have special requirements. Weekend Availability: I also offer weekend care, ensuring pets aren’t left alone during your time away, with plenty of opportunities for exercise, attention, and even trips to pet-friendly locations. No matter the time of day, your pet's well-being is my priority, and I will ensure they’re happy and healthy during your absence. I create a safe, pet-proofed environment in my home and follow your pet’s routine closely. I provide constant supervision, offer regular updates, and ensure their comfort.

“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: I have had dogs and cats my whole life,my entire family loves animals I am very flexible because I know everyone cares for their pets differently I totally fine with any special cases under humane circumstances.Am doing this as a work at will job because after working for the aspca I have learned that pets are a essential part to anyone’s life.I also work as delivery biker so this job fits into my schedule, my hope is that before the end of the summer I have my high school diploma paid off Nd u have earned enough to purchase a car with no lease. I have high hopes for myself and I thank you for reading my bio and look forward to working with your lovely pets. Am a independent contractor so I work from home 10-20 hours a work am able to watch dogs at the same time I have treats and doggy tv. I have a fenced in yard and one fur baby to keep your dog company and I have a extra large crate if needed my little girl daisy is a small dog she on only likes to play with small dogs

“Nikki is sweet, responsible, and exudes positive energy. My cats instantly gravitated to her, and I'm grateful for her flexibility and responsiveness. If you're looking for a local pet-sitter specializing in cats—look no further!”

Clayton L.

About: I’ve spent the last 11 years caring for my elderly Chow Chow, and during that time I’ve also watched lots of other dogs, including two golden retrievers. I’m experienced with everything from playful pups to seniors who need gentler care. I also volunteer at local shelters walking dogs big and small, which has taught me how to build trust quickly and handle every kind of temperament. I’m calm, patient, and I always make sure each dog feels safe, loved, and full of treats. 😘 I'm currently working part-time, so I'll have plenty of time to play with your pups! I'm available for boarding on all weekdays and some weekends, just ask! When I’m caring for a dog in their home, my goal is to make sure they feel completely safe, comfortable, and loved while you’re away. I follow their normal routine as closely as possible with the same feeding times, walks, and favorite spots. I’ll make sure that everything feels familiar and stress-free. I’ve spent over a decade caring for my senior Chow Chow, so I’m especially patient and gentle with older dogs or those who need a little extra attention. I’ve also watched younger, energetic pups like golden retrievers and volunteer regularly at shelters, so I’m confident handling dogs of all sizes and temperaments. I always make sure pets get the right mix of exercise, play, and calm time. I send photo updates and messages regularly so you can relax knowing they’re happy and in good hands. Your home will be left just as you found it — clean, secure, and filled with tail wags.