Chicago Dog Walkers in Chicago, IL

Meet the owners

Ryan & Caroline

Hi, we’re Ryan and Caroline Fields, the husband-and-wife team behind Millennium Dog Walkers & Pet Care!

In 2025, longtime owner Al Olsen officially passed the leash to us, and we feel so lucky to be carrying MDW into its next chapter. Al started Millennium Dog Walkers in 2010 and built it into something really special: a trusted, neighborhood-focused pet care company with amazing clients, wonderful walkers, and a whole lot of dogs and cats who have become part of the MDW family.

We’re originally from Milwaukee and recently made the move to Chicago with our dog, Milly, and our cat, Mazie. We have absolutely loved getting to know the city, from long walks through different neighborhoods to trying new restaurants, exploring the lakefront, and seeing just how many Chicagoans are as obsessed with their pets as we are. When we’re not working on schedules, talking with clients, or checking in with our walkers, there’s a good chance we’re out wandering the city, planning our next trip, grabbing something delicious to eat, or hanging out at home with Milly and Mazie.

As pet owners ourselves, we know how big of a deal it is to trust someone with your dog or cat. We don’t take that lightly. Our goal is to make Millennium Dog Walkers feel reliable, easy to communicate with, and genuinely caring from the very first message. We want our clients to feel like they have real people in their corner, and we want every pet to feel safe, loved, and excited to see their walker.

Today, MDW is made up of an incredible team of dog walkers and cat care specialists providing dog walking, puppy care, senior pet care, cat visits, and overnight pet sitting throughout Chicago. We’re so grateful to Al for everything he created and for all of his guidance during this transition. We’re honored to keep building on his legacy while bringing our own energy, love for animals, and personal touch to the business.



At the end of the day, we’re just really happy to be here: caring for pets, getting to know their people, and being part of daily life in so many Chicago neighborhoods.

Ryan Fields

Ryan brings a calm, steady energy to every walk (and every pet!). With a background in finance and operations, he’s all about keeping things organized behind the scenes - while still getting plenty of tail wags along the way. He’s known for winning over even the shyest pups with his gentle approach and genuine care. Outside of dog walking, you’ll find him exploring the city with Caroline and their dog Milly.

Caroline is a lifelong animal lover. She has a background in business and design, but finds the most joy in connecting with pets and their people. Whether she’s out on walks or behind the scenes keeping things running smoothly, she brings warmth, creativity, and a serious love for dogs to everything she does. Her sidekick is Milly, a rescue pup with a big personality and even bigger heart.