Chicago Dog Walkers in Chicago, IL

Meet the owners

Ryan & Caroline

Millennium Dog Walkers & Pet Care is entering an exciting new chapter! In 2025, longtime owner Al Olsen passed the leash to new owners Ryan and Caroline Fields, a husband-and-wife team with a deep love for animals and a background in the pet industry. Originally from Milwaukee, Ryan and Caroline recently moved to Chicago with their dog Milly and cat Mazie, and they’re thrilled to carry forward the exceptional service MDW is known for. With years of experience in animal care and business operations, they bring a fresh enthusiasm and heartfelt commitment to pets and their people across Chicago. Al has been an incredible mentor during the transition, and Ryan and Caroline are honored to build on the legacy he created.

Millennium Dog Walkers & Pet Care is comprised of expert dog walkers and feline specialists. We provide dog walking, puppy care, senior pet care and overnight petsitting in 19 of Chicago’s Neighborhoods. Its previous owner, Al Olsen, retired early 10 years ago and moved to downtown Chicago in 2009 to be close to 3 young grandchildren. His retirement was short lived as he started MDW & PC in 2010 thinking it would keep him busy 4-5 hrs. a day in his early days of retirement. Within 4 months it was a full time job that Al has never regretted making. In his words, it’s been the best 8 years of my working career.

Every year MDW connects with its’ clients to raise money for one of the city’s Rescue Centers. Ryan, Caroline and their walkers find this to be very rewarding, and their clients have been most generous. At the end of each day, Al can be seen walking Sugar Bear, his golden doodle, on the streets and Riverwalk in Streeterville.

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.