Our Story

Using the Internet To Get Off The Internet!


The Windy City Explorers began in 2009 when Tom & Chantal wanted to visit neighborhoods across the city. We began with just a few friends and then joined the Meetup platform. Soon, people began coming out of the woodwork. Our initial participants began to bring their friends and the momentum grew. We've hosted nearly five hundred events and enjoyed the camaraderie of nearly eight thousand people! We must be onto something because people keep coming back! Our adventures continue and the only thing missing is YOU!


You may wonder WHY do we produce these events? And why are they free?


These events are free so that we can always continue with our 200% money back guarantee. If you're ever dissatisfied with any free event, we'll refund you 200% of the price you pay us!


We produce these events because we LOVE PEOPLE! We love to bring people together from all walks of life for friendship, camaraderie and walking! After you get to know us, you may come to learn that your hosts Tom & Chantal are Realtors and that we'd love to help you buy, sell or rent your next dream home! Tom is also an estate planning attorney and he'd love to help you get your affairs in order. But really, we love these events as much as our participants..... it's just good clean fun and we'll keep producing them as long as people keep coming back!