5 Best Dog Walkers in Chicago (2026)

Windy City Dog Walkers has served Chicago since 2002, offering daily dog walks, cat care, and pet sitting with a specific policy of assigning the same walker to each dog rather than rotating staff. The company is licensed, bonded, and insured, and runs an app for scheduling, invoicing, and messaging directly with your walker. It holds the highest review count of any dog walker on this page.

Majestic Paws Chicago is an Old Town dog walking and pet sitting business run by an owner reviewers describe as easy to reach directly. It handles multi-dog households, including reviewers with both a very large and a very small dog on the same walk, and also covers cat sitting for owners traveling. It posts a perfect rating on this page.

Millennium Dog Walkers & Pet Care has served Chicago for over a decade from its Streeterville-area base, offering dog walking and cat care with a policy of charging for only one dog if you have two. Reviewers specifically mention using the service to work around irregular schedules, including healthcare shift work, with easy last-minute changes and cancellations.

Paws For Walks Chicago LLC is a Lakeshore East dog walking, daycare, boarding, and pet sitting business, founded in 2013 and describing itself as woman and LGBTQ owned. Reviewers mention using the service specifically during recovery from surgery or other situations requiring reliable, flexible support, alongside standard daily walks and cat sitting for travel.

Dogs Deserve It is a Lakeview dog walking and pet sitting business that reviewers describe using for as long as 15 years. Its end-of-walk reports include detailed notes down to bathroom habits and whether the water bowl was refilled, and it also offers overnight in-home pet sitting for longer trips.