Chicago’s Parks Take Center Stage: 'What’s Out There Weekend' Brings Free Expert-Led Tours to the City’s Greatest Landscapes

Chicago’s beating heart has always been its parks. From Frederick Law Olmsted’s sweeping visions to Jens Jensen’s prairie-inspired artistry, the city’s green spaces are as much a part of its DNA as the lakefront skyline. This fall, Chicagoans and visitors alike will get the rare chance to step inside that legacy during What’s Out There Weekend Chicago, a two-day deep dive into the city’s open-air soul.

On October [insert date], the Cultural Landscape Foundation (TCLF) — the Washington, D.C.-based nonprofit known for defending and celebrating America’s cultural landscapes — will host more than 30 free, expert-led tours of Chicago’s parks, gardens, and open spaces. Think of it as an all-access backstage pass to the city you thought you knew.

This isn’t just about pretty lawns and public benches. It’s about discovering the hidden backstories — the architects, designers, and big personalities — behind the spaces that shaped how Chicago moves, breathes, and connects. From Humboldt Park’s historic lagoons to Grant Park’s sweeping lakefront, guides will share the kind of inside stories that turn everyday strolls into epiphanies.

The Cultural Landscape Foundation knows Chicago well. Its bond with the city runs deep: the organization handed out its first-ever Stewardship Excellence Award to former Mayor Richard M. Daley back in 2001, and has since collaborated with the Chicago Park District, the Chicago Architecture Foundation, and countless cultural groups. Now, after hosting similar events nationwide for 15 years, What’s Out There Weekend returns to Chicago for only the second time since 2011.

Alongside the tours, TCLF offers a free, ever-growing digital guide to more than 75 Chicago sites and 60 designer profiles — GPS-enabled and ready to use on your phone. Prefer something you can hold in your hands? Grab the What’s Out There Weekend Chicago Guidebook for just $14.95, or download the full version as a free PDF at TCLF.org.

For architecture buffs, park lovers, and curious Chicagoans, this weekend is more than a walking tour — it’s a love letter to the city’s cultural landscape legacy. Whether you’re a tourist with a camera or a local who thinks they’ve seen it all, prepare to be surprised.

Pro tip: Registration is free but required. Go to TCLF.org to lock in your spot.

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