Pet Care Service In Chicago

Ryan & Caroline Fields | Al Olsen

Ryan and Caroline are the proud new owners of Millennium Dog Walkers & Pet Care, stepping in to lead with a deep respect for the legacy Al built and a shared passion for animals and community. After years of running their own pet-focused businesses and working closely with clients and their furry family members, Ryan and Caroline knew they wanted to bring that same passion and personal touch to a new chapter in Chicago. They moved from Milwaukee in 2025 and quickly fell in love with the city's energy and its dogs. With backgrounds in operations, customer service, and animal care, they’ve combined their skills to lead Millennium Dog Walkers with heart, reliability, and a strong sense of community. When they’re not managing daily operations or checking in on pups, you can usually find them exploring the city’s neighborhoods with their dog Milly (a very proud Chief Barketing Officer) and keeping things running smoothly with the “help” of their opinionated cat Mazie.

MDW's previous owner, Al Olsen, is a resident of Chicago’s Streeterville neighborhood. His most recent beloved dog is a golden doodle, Sugar Bear. She is one smart, energetic and playful dog…and has been a great addition to his family! Prior to Sugar Bear, he had a miniature schnauzer, Maxwell. Max lived fourteen wonderful years. In fact, his children think that Max got better treatment than they did. There’s nothing he wouldn’t do for him.

Every year, Millennium Dog Walkers utilizes its resources to help raise money for one of the many pet rescue organizations in the city of Chicago. Most recently, that organization has been The Anti-Cruelty Society. Our clients have been very supportive and welcome the opportunity to assist the various rescue organizations.

Millennium has been in business for twelve years and employs expert dog walkers and feline specialists, all of whom share our passion for dogs and cats. They are all current or past pet owners, are Bonded and Insured, and must pass a background check before being hired.

All in all, Millennium’s commitment to you and your pet is to accommodate your pet’s needs and in the process make you comfortable and confident that your pet is in good hands.

Top Dog, Millennium Dog Walkers