Dog Walking Hillside
Book a dog walker to give your dog a 30-minute walk around your neighborhood.

Hillside, Find top rated dog walking
Prices are estimates per walk. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Jodi is so great! She is very flexible with my last minute booking and has been great with our dog! She presents with great communication as well! Would recommend!”

About: What sets me apart is both my personal and professional experience caring for animals of all ages, sizes, and personalities. I’ve grown up around dogs my entire life and currently work at Dogtopia, where I care for and supervise dogs daily. This has helped me become patient, attentive, and comfortable working with different temperaments and energy levels. I also have experience with both senior dogs and puppies. My senior dog, Otis, had arthritis, so I learned how important patience, comfort, and attentive care are for older pets. I also helped raise and train our pug puppy with basic training, routines, and socialization. Because of these experiences, I understand that every pet has different needs depending on their age and personality, and I always try to make pets feel safe, active, and cared for like they’re my own.⭐️😊 Pet care is already a big part of my daily routine. I work at Dogtopia, where I help maintain a safe, clean, and fun environment for dogs of all sizes and personalities. 🐾 My job has taught me the importance of paying close attention to dogs’ behavior, safety, and overall well-being throughout the day. When I’m home, I also spend a lot of time caring for my own dog. I enjoy taking him on long walks by the lake, staying active with him through runs and playtime, and making sure he gets plenty of attention, exercise, and care every day.🦮🏃♀️❤️ When caring for pets in my home or a client’s home, I always prioritize safety, comfort, and keeping pets on their normal routine as much as possible. I make sure the environment is clean and secure by checking doors, gates, food, and anything that could be unsafe or easily gotten into by curious pets.🤗 I also pay close attention to each pet’s behavior, energy level, and individual needs to help them feel comfortable and stress-free while their owner is away. Whether it’s feeding, walks, playtime, medication reminders, or simply giving them attention and companionship, I always try to make pets feel safe, cared for, and at home.
“Jessica went above and beyond all expectations! She was great with Sullivan and even brought in a package off of our porch when she dropped sully off. Amazing walker and will definitely book again! ☺️”

“Mikalanne was amazing- she was able to walk my dog every day for a week after a last minute request. She communicated well and was very accommodating. Highly recommend!”

“Nothing but great things to say about Jackie! She was able to walk Jenko on a last minute request. Have used her on multiple occasions since. Great communication and follow up. Definitely recommended her for any dog walking needs”

“Jessica is amazing! Our dog Gabby stayed with her during the day and they got to enjoy nice walks, go to the park and get lots of play time. Jessica kept us updated during the day and sent us lots of cute pictures. Gabby is excited to see her again!”

“Jessica took the best care of Max! Her communication was impeccable and you could see the quality in her care she provided for our dog. We could tell Max looked forward to his walks with her. We would highly recommend her care with anyone’s pet!”

“If you’re looking for a dog walker I highly recommend Melissa. She was prompt, professional, and took excellent care of my small dog. She asked relevant questions about my dog before leaving for the walk, and afterwards gave me a thorough update of the walk. I feel comfortable with her in charge of my beloved sweet furry friend!!”

About: My sister and I grew up playing and helping our older neighbors in the area walk and take care of their dogs. My family has had cats my whole life that I’ve had experience taking care of. In high school I’d house/pet sit friends & family friends’ dogs & cats while they were on vacation, & started rover sitting during college! An actor, bartender, & graduate of UWMilwaukee with an open schedule! Looking to fill that time taking care of, spending time with, and getting to know your pets! I love the outdoors and I can take your dogs on lots of walks based on their needs! I always check if doors are locked before I leave/sleep & make sure to put away anything that pets can get into if they are left to roam. I stay clean so I make sure to clean any mess I or the pets create. I can also crate your pets if needed.
“Travis did a very good job walking my dog Mikah while I was away. He is very friendly and my dog warmed up to him instantly. He was very persistent with the report cards and sending photos. Definitely would work with him again and recommend!”


About: I have worked at a dog and cat boarding center for 3+ years now, and have exceptional experience in animal care. I also recently adopted a dog of my own this past year, which has taught me a lot about day to day life with dogs! I am currently a college student who has mostly online courses. I have a lot of free time and a passionate love for animals, so why not combine it into one! I have my own dog that I care for deeply, and would treat your pet as if it were my own. Making sure your pet is well cared for and happy is always my goal!
About: I have always had a dog ever since I was a little girl. As I got older, I started walking my neighbors' dogs and dog-sitting, and I even considered being a vet for a while because of my passion for animals. I’m a graduate student at Marquette University. I have flexibility this semester to spend ample time with dogs and take them on walks. I can come in the mornings and at nights, depending on the day. I have always had dogs and can handle a wide range of sizes. My childhood dog was 125 pounds, so I can handle big dogs and little ones too. I know how to properly walk them and care for them.
About: I have worked at a dog daycare for the last 7 years and have watched friends, family, and neighbors pets including dogs, cats, and lizards. I also babysit. I am now working as a dolphin trainer and am usually only available on my days off, but the timing of my shifts does vary daily and weekly. I just moved to the area so caring for your pets will help me get to know the area better. I am a full time zoological specialist so I’m really only available on my days off or if your pet is okay on their own for a longer period of time. I am currently in an apartment so I am only able to come to clients homes, but that doesn’t mean my level of care is any less!
About: Hi there! I’m Karla DJ, your soon-to-be pet care companion! By day, I work at a desk with computers, so I cherish the breaks I get to spend caring for pets—it’s the perfect way to recharge! In my free time, I love DIY projects and training my own dog, Lola. I’ve been an animal lover all my life, growing up with two turtles, a guinea pig named Bobo, a Shih Tzu mix named Chucho, and a Pomeranian named Princess. Over the years, I’ve also been a rescue mom and the go-to dog sitter for friends and family. One of my favorite stories? While living in Houston, I met the sweetest rescue pup and instantly knew she was meant to be mine—that’s how Lola, my loving Carolina mix (and partner in crime!), joined my life. Now, as I train Lola at home, I’d love to extend that care to your pets too! Whether it’s a refreshing walk, a fresh bowl of water, or some extra playtime and treats, I’m here to make their day brighter. Plus, I live with my sister, so your furry friends will get double the love and attention! I can’t wait to meet your pets and help make their days happier! I'm a morning person and my day starts a 5am! With so much time I'd love to be more productive and help others with their pets. I'm available all day Saturday to Sunday and during the week depends but very flexible from Monday to Wednesday. **I'm happy to help with all your pet care needs!** Whether it's refilling food and water, administering medications, keeping your home pet-secure, or providing walks and car rides - I've got you covered. Your pet's comfort and safety are my top priorities! Let me know how I can best care for your furry friend. I look forward to helping!
About: I don't actually call myself that, that's what my friends say I am. I've literally never met a dog I didn't get on famously with. I respect the fact that they are individuals with their own needs. I don't mean to sound too self assured with the title, but I earned it from friends. Whether it's running on the Lake Michigan shore or just finding a nice sunny spot to sit for a while, your pup is going to have a fulfilling day. I have huge flexibility so no worries! A last minute trip or planned weeks in advance, we can work something out. I'm here for you! Even same day! I strive for communication as much as possible between animal and human. If they're not feeling like socializing, I don't force anything. Everyone has different needs. My experience in a dog daycare really helped me read and understand dog body language to head off any issues that may arise when you're watching 12 dogs.
About: I’m a regular dog foster and walker at MADACC, so I’m comfortable catering to all different pup personalities and needs! I’ve taken care of all kinds of dogs since I was young, from puppies to senior with medical needs. I work remote 3 days a week and have no pets of my own, so I have lots of availability to give your dog the attention and care they need! Whether you’re looking for a walker or somewhere to take your pup for a long weekend, I can make most things work. I have a spacious apartment in a dog-friendly building where your dog will have plenty of space to lounge around! I live close to the Summerfest grounds so I have plenty of access to green space for long walks, or just a quick jaunt around the block depending on their preferences. I treat every dog I care for like my own, so you can rest assured your pup will be well cared for with me!
“Needed someone to look after my dog while I was working during the holidays and Gabi did a great job at looking after him and sending updates. Would absolutely recommend and book again!”

About: Experienced in long term pet care, taking care of dogs for extended time periods when owners are on vacation and everyday experience taking care of pets while families are working, including drop ins and dog walks I work remotely and have a lot of free time open during the day for drop ins and dog walks. I’m available in the mornings, afternoons, and nights! Will respect any rules of the house and am very open to watch / play with the dogs in any way they’re comfortable with and used to
The median cost per walk for dog walking in Hillside is $20
Dog parents share their Rover experiences - Hillside
Maggie is great; she's been walking Bella, a Pittie who is often in the seek-and-destroy zone. She is hyper-focused on everything around her, but never on her handler. Bella Francis is my daughter's dog, who has been staying with me for the past three weeks. We hired Maggie to get Bella out on 4 30-minute walks per week, and she was a lifesaver. Thanks for everything, Maggie. If you need a walker who can handle anything and everything with a smile, I would highly recommend Maggie. She is 10 stars!

Dana has been fantastic to work with and has taken great care of my dog, Vincent! She is thorough, attentive to details, and always sends reliable updates during/after her visits. She is also very responsive and flexible whenever last-minute schedule changes come up, which I really appreciate. Vincent and I would highly recommend Dana to anyone in the Milwaukee and Third Ward area looking for a reliable, trustworthy person to care for their pet!

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- Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
- Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
- 24/7 support from the Rover team–here to help if you ever need someone to talk to.

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Reservation protection
It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.
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