Chicago Passive Income Society Meetup

We're proudly rooted in Chicago, but our mindset is global. While we host meetups and local events around the Windy City to connect in person, our real base is anywhere the Wi Fi is strong and the views are better. Chicago is our launchpad a vibrant, entrepreneurial city that fuels our curiosity but our community is built for those who believe work shouldn’t keep you in one place. Whether you're sipping coffee in Logan Square or typing from a beach in Bali, you’re part of the tribe.

We believe diversity isn’t just welcomed it’s essential. Our group is committed to creating a space where everyone feels seen, heard, and respected, no matter their background, identity, or journey into remote work. We set clear expectations from day one: kindness, active listening, and open mindedness are non negotiable. If conflicts come up, we handle them with empathy and accountability, because trust is the foundation of any real community. This isn’t just a meetup it’s a support system built on mutual respect.

Big wins deserve big celebrations, and we love shining a light on our members’ wins whether it’s landing a dream client, hitting a passive income goal, or finally booking that one way ticket to Lisbon. We share achievements during our meetups, give shoutouts in our community updates, and sometimes even organize small toasts over rooftop drinks in Chicago or beachside dinners on group trips. Milestones are proof that this lifestyle isn’t just possible it’s happening, right here, right now, with people just like you.

If you’ve ever dreamed of working from a new city every month, building income that follows you, or finding your people while building your future this is your sign. The Chicago Passive Income Society isn’t just about making money online, it’s about designing a life that moves with you. We’re all about real connections, real experiences, and real freedom. Come join a community that’s already out there doing it and ready to help you do it too.