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Chicago · Adventure · Community

Explore beyond the skyline.

For Chicagoans in their 20s and 30s who crave more than the city grid — from lakefront sunrises to weekend trails you've never heard of.

Join the Community See Adventures →
300+ Chicagoans exploring together
🌿 Lakefront Hikes✦ Weekend Camping✦ Hidden City Trails✦ Kayak the Chicago River✦ Indiana Dunes Day Trips✦ Stargazing Getaways✦ Urban Exploration✦ 🌿 Lakefront Hikes✦ Weekend Camping✦ Hidden City Trails✦ Kayak the Chicago River✦ Indiana Dunes Day Trips✦ Stargazing Getaways✦ Urban Exploration✦

Who We Are

Born in the city,
drawn to the wild.

We're a crew of Chicagoans — 20s and 30s somethings — who refuse to let city life be the whole story. Outdoorsy Chicago is where your neighborhood crew meets trail runners, kayakers, rooftop gardeners, and weekend wanderers.

Whether it's a sunrise at the Dunes, a midday bonfire along the lake, or finding a park you've never noticed in your own zip code — this is your community for all of it.

300+
Members
48
Adventures Run
19
Neighborhoods
7
States Explored
Into the woods 🌲 Into the woods
On the water 🚣 On the water
City trails 🌆 City trails

What's Coming Up

Upcoming Adventures

Our main calendar — this is always the most up to date. Check here first before looking anywhere else.

⚠️ Some events are also posted on Meetup.com, but not all events appear there. This calendar above is always the most complete and up-to-date source.

Join the Community

Tell us about yourself.

We're building something for adventurous Chicagoans like you. Share a bit about what you're into so we can plan adventures that actually get you off the couch.

Takes 2 minutes. No spam — just good trips.

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🌿 You're in! We'll be in touch with upcoming adventures.