Dog Sitting Winnetka

About: I’ve been caring for pets of all ages—from playful puppies to gentle seniors—for over 20 years, and it’s something I truly enjoy. I know how much your pet means to you, and I strive to care for each one with patience, kindness, and attention. My hope is that your pet feels comfortable, loved, and at ease while you’re away. I offer house sitting and in-home care so your pet can stay in the comfort of their own home and keep their usual routine. I enjoy quiet, steady walks and always stay aware of our surroundings, making adjustments based on your pet’s needs and comfort level. Every walk and care routine is tailored to your pet’s personality, pace, and preferences. I also understand how hard it can be to be away from your furry family member, so I’m happy to send plenty of photo updates and messages to help you feel connected and reassured. You can trust that your pet will be cared for gently and thoughtfully, just as if they were my own. I'm employed full time with a flexible work from home schedule which will allow for me to care for your pet during the day (my breaks) as well as longer walks on my lunch break. I can also work with your schedule to do earlier morning shifts or later after work shifts. I have a puppy at home that we're still training, so I'd keep your pet close to your home/yard. I would ensure their safety by making sure to keep a tight handle on their leash as I look for upcoming obstacles (other dogs, kids, people, etc.) to make sure they're going to be ok on their walks. I would also closely monitor them as they go outside in their yard.

About: I offer in-home pet sitting and dog walking for local clients, providing feeding, exercise, and companionship for both dogs and cats. I'm comfortable administering medications and following individualized care instructions for pets with specific health or dietary needs. I've built lasting relationships with repeat clients through reliable scheduling, attentive care, and regular updates on their pets while they're away. I manage all bookings and client communication myself, balancing multiple pet-sitting clients alongside full-time work in animal care. I have flexible availability throughout the week, including daytime hours, which means I can stick to a pet's normal routine without rushing, whether that's multiple walks a day, mid-day feedings, or checking in on medication schedules. I'm able to be consistent and present, so pets get the same reliable care and attention every visit. I treat every home like it's my own, securing doors, following the pet's normal routine for feeding, walking, and litter boxes, and sticking closely to any medication or care instructions. My clinic experience helps me catch early signs if something seems off, and I know how to let anxious or senior cats warm up at their own pace rather than forcing it. For dogs, I double-check leashes and collars and stay attentive on walks. I keep owners updated throughout, so they always know their pet is safe, comfortable, and cared for.

About: Hello, pet parents! Your pup is in for a treat! I enjoy going on adventures! We check out state parks, forest preserves and beaches during our time together. I take lots and lots of photos to help capture the magic and share the fun with you. Of course for pets with more of a relaxed temperament, cuddles, belly rubs and more low key quality time is also greatly enjoyed. I look forward to spending time with your pup! I work from 9am-5pm, 5 days a week, so any time I'm not at work, your pet receives my undivided attention and care. I'm very detail oriented and tidy. What ever your dogs routine is, I'll adapt. I'm also a neat freak so I do a great job of leaving your place cleaner than you left it.

About: I’ve been a huge dog lover since I was ten years old! Growing up, I pet-sat for neighbors, family, and friends, so I’m very comfortable with feeding, walking, and keeping pups entertained. I’ve owned three dogs throughout my life and am currently a proud Shih Tzu owner, so I definitely know my way around a big 'lion dog' personality! I also enjoy training; I’ve taught my dogs everything from basic sits and paw-shakes to 'wait' commands for meals and even some fun moves like dancing. I truly just love being around dogs! I'm currently a full time college student but I still have lots of time to play and take care of your dogs! My availability is usually in the afternoon on weekdays and mostly open throughout the day on weekends. Just send me a message and I'll coordinate as best with your times! When sitting in your home, my priority is maintaining your dog's familiar routine to keep them stress free. I stick to your established feeding, walking, and medication schedules! And I make sure to have fun with them :)

“Jesse is a real sweetie with our cats. She was available and communicative and very caring towards our animals! Thanks Jesse!”

Ashley J.

About: I’ve taken care of dogs of all breeds and size's. Friends, neighbors, and family often rely on me to walk, feed, and bathe their pets while they’re away. I’m comfortable with senior dogs, energetic puppies, and pets with special routines. Whether it’s daily walks, playtime, or overnight care, I always treat every pet like my own. I currently have a flexible schedule that allows me to provide morning, midday, and evening visits during the week. Weekends are open for walks, drop-ins, or overnight stays. I’m responsible, communicative, and happy to provide updates and photos so you can relax knowing your pet is in great hands. I live in a pet-friendly apartment that’s clean, safe, and comfortable for your furry friend. I take frequent walks and make sure pets get plenty of exercise and attention throughout the day. I’m very mindful of leash safety, secure entrances, and keeping pets calm in new environments. Whether your dog loves outdoor strolls or prefers cozy naps, I make sure they feel happy, safe, and cared for.

About: No two dogs are the same, and I adjust my care to match. I have experience with puppies — including reinforcing basic commands and helping build good habits early on — as well as senior dogs, where I adjust to a slower pace and give extra attention to comfort and mobility. I pay close attention to each dog's personality and energy level, adapting my approach whether that means more playtime and structure for a young pup or a calmer, gentler visit for an older dog. I communicate clearly throughout every visit with updates and photos, and I always leave things clean and tidy behind me. Available for house/pet sittings and drop-ins all week. Guaranteed evenings and flexible during the daytime. Let's chat and coordinate the best care for your pet! I come to your home so your cat can stay in their own comfy space, sticking to their normal routine for feeding, litter, and playtime. I handle litter care thoroughly no matter the setup, and if your cat needs medication, I make sure it's given on schedule and exactly as instructed. I pay close attention to how your cat's doing — energy, appetite, mood — and I'll send you updates and photos so you're never left wondering. And of course, I always tidy up before I go, so you come home to a happy cat and a clean space!

“Taylor did a meet and greet before our booking. We enjoyed getting pics and updates on our dog's activites while we were away. She went the extra mile to bring in our mail. Would for sure rebook with Taylor!”

Emily R.

“We were very pleased with Ariel’s drop ins to care for our dog. She was prompt and arrived when scheduled. She sent a picture of our pup enjoying some time outdoors. We would have her come again.”

Renee F.

About: I have been a dog lover my entire life so being around dogs comes very natural to me. Growing up with dogs has given me hands-on experience with daily care such as feeding, walking, bathing, playtime, cuddles, and providing lots of love and attention. I have cared for many different dogs over the years, each with their own personality, routine, and needs. I am very adaptable and am more than willing to follow a schedule and routine that fits your dog's needs. My highest priority is to provide safety and comfort to every dog I meet and care for. I'm currently a college student, which gives me a flexible schedule and allows me to be available for dog walks and drop in visits. Weekdays (Tuesday-Thursday) I am available after 4 pm. Whenever I am spending time with a dog, I make sure they are in a safe, calm, and loving environment. I treat every dog as my own and ensure that they are content. I will be attentive to your dog's comfort, so it will be no issue to adapt to their needs and routine. In addition, I am more than willing to send updates so you can see how your dog is doing throughout our time together :)

About: Work from home professional with car that is dog-less but providing "uncle" love, care, and support to other willing and open dogs! Grew up with dog (15 years) and co-parented another for 5 years. Recently official dogsitter for numerous friends and co-workers. I pay them :) Have experience with mid and large sized dogs. Have a large closed balcony and live adjacent to a large park. I do not provide any sort of grooming services but can provide simple medication. Am obsessive overbearing and will consider safety of your animal above all else. I can host animals at my home or do in-home visits. Prefer to host and live alone, working full time here If you have any other questions don't hesitate to reach out! Work full time at home and currently no other pets in the home, allowing me to give 100% attention to your loved ones while you are gone! I have a secure outdoor balcony, multiple doggie beds in my 1 bedroom, 1 bath. Live by myself so no in/out activity of other people. Park nearby for short and long walks.

About: I’ve grown up with dogs and have recently started taking care of many others! No dog is a “bad dog” to me whatever your pets need I can attend to them. I also have cared for multiple pets in one house hold so I am great at making sure all your furry friends get love! I recently moved to Chicago and have a very open schedule to walk, feed, play, and pet sit for your dogs and cats whenever they need! I like to follow your pets schedule as close to how you do. I know owners leaving the house and a new person and scent coming in can be stressful for them, so I like to keep them on their routine so the temper change doesn’t scare too much!

“My dogs love her!”

Alexandrea A.

“Bridget is thoughtful and caring. She sent lots of great updates and photos through the day!”

Judy W.

About: I’ve had both dogs and cats since I was five years old—life just doesn’t feel complete without a furry friend by my side. After the passing of my own pets, I realized I still have so much love to give. That’s why I’ve found real joy in fostering and caring for other people’s pets—because to me, it’s all about sharing love and companionship. Whether it’s snuggles on the couch, long walks, or playtime (and more playtime!), I’m here to make sure your pet feels safe, loved, and completely at home—whether that’s in your space or mine. I work part-time with a flexible schedule, so chances are good I can match your pet’s routine and work around your calendar—allowing me to spend quality time with your pet when they need it most. When your fur baby is with me—whether in your home or mine—they’re part of the family! I stick to their usual routine, whether that means long walks, zoomies in the yard, or couch snuggles (my personal favorite). I don’t have any pets right now and my children are grown, so when they stay with me it’s a one-on-one hangout—just me and your fur baby getting all the attention they want. In your home, I’ll keep things just the way they like it, with lots of love and playtime mixed in.

About: I have a lifetime of experience caring for animals, having grown up on a farm where I looked after dogs, cats, and larger animals from a very young age. This background taught me how to read animal behavior and handle different temperaments with patience and care My schedule is very flexible for walks, feeding, and playtime. I am typically available in the early mornings until 7h30, afternoons and on weekends, but I am always happy to discuss specific needs to see if I can make it work for your schedule! While I generally do not host pets at my home, I am open to discussing boarding options for urgent situations. I am very responsible and attentive to instructions, ensuring your pet's routine is followed exactly as you prefer. Your pet's safety and happiness are my top priorities!

About: I just graduated from UMass Amherst with a degree in Pre-Veterinary Science. I have grown up with pets and taken care of them for years! I’ve had dogs, cats, chickens, hamsters, guinea pigs, and fish! I have a lot of experience taking care of animals as I’ve interned at a zoo and volunteered at shelters and vet clinics. I’m very comfortable giving medications to pets as I’ve had a lot of practice with this with my own pets and while sitting! PLEASE READ** I am currently traveling in Europe and will not be home until October 10th. I am available after that for meet and greets or I can do virtual meet and greets as well! I am looking to move states in the coming months so I will not be available for long term sitting. My house has one kitten, and my backyard is not fenced in. I’d love to take care of your pet in either your home or mine, whichever is easiest!

“Timothy took such great and gentle care of my cat, Pepper! I felt very safe leaving her in his hands. This was my second time working with Timothy and I will definitely be asking for his help again!”

Connor W.

About: Since I was a teen, I've always been the go-to person asked to pet sit for people when they went on vacation. I've done it for 10+ years. I recently graduated from law school in May, and I am currently studying for the BAR. I would love to make some money on the side, caring for your special guys and girls! Currently, I have full availability because my sole focus is studying for the BAR. So I can make myself available at any time day or night! I love animals, and I recognize how much they crave attention, especially when they're missing their owner. I would love to provide that necessary attention in your absence. I will make sure that your place is the same as it was when I got there. With a fresh litter box cleaning for cats.

About: Student with open availability and many years of dog care experience. I used to care for my own small dog and on occasion my friends two puppies or currently my friends pit-bull and cat pictured. I love all animals but dogs are my favorite. I care for dogs just as I care for humans because they aren't just animals they are family. I treat my family with the upmost respect and tend to their ends as they come. Your dog and cat will be well taken care of not just because it is my responsibility but because it is something I enjoy. Playing, exercise, feeding, nap time, etc are all things I enjoy to do with dogs and any other special services your dog may require is completely welcome as well. I am a dog person 100% I am available in the early mornings and evenings after 5pm with open availability on the weekends. Otherwise I am working or completing my daily commute throughout the city of Chicago I will follow the care instructions provided by the owner in their home. I will conduct my job in a safe efficient manner. I will stay on task and provide your pet my full attention. When job is complete I will leave and if I have any issues I will always keep communication open and flowing with the owner.