Choose Your Own Adventure – Fall 2025

Tue, Sep 16
3:45pm – 9:00pm(ish)

Register for your top 3 choices here!

Here’s what you need to know:

  • All sessions include dinner.
  • Each session is assigned on a first-come, first-served basis.
  • Fri, Aug 29 is the deadline to register your session preferences (you rank your top 3).
  • While we try to give you a break after the day’s meetings, some CYOAs will have to start on the earlier side. Please make note of the lobby departure times when making your choice.

SOLD OUT – Urban Ecology in Action: The Wild Mile Experience

Capacity: 15
Dinner: El Tragón

Get a behind-the-scenes look at the Wild Mile, Chicago’s pioneering floating eco-park.

Built atop the North Branch Canal of the Chicago River, this innovative project is transforming the urban waterway into a thriving habitat for native plants, fish, and birds.

On this private tour, you’ll learn about the bold vision behind the park and even get your hands a little dirty with light volunteer activities.

Afterward, we’ll head to Off Color Brewery to enjoy craft beers paired with Mexico City–style tacos from El Tragón.

This group departs from the lobby at 4:15pm.


SOLD OUT – Bootleggers & Barrels: A Prohibition-Era Experience

Capacity: 22
Dinner: District Brew Yards (BBQ)

Step back in time with The Barrel Run for a spirited journey through Chicago’s Prohibition past.

You’ll climb aboard a vintage-style barrel bus and cruise through the city’s historic streets while expert guides share colorful stories of gangsters, bootleggers, and secret speakeasies.

This private tour blends history, humor, and immersive storytelling—bringing to life the people and places that made Chicago a Prohibition hotspot. Along the way, you’ll enjoy food and drinks inspired by the era, for a lively evening of stories, sips, and Chicago lore.

Leaves from the hotel lobby at 4:30pm.


Living Histories: A Tour of Pilsen & Little Village

Capacity: 15
Dinner: Los Comales

Join local historian and founder of Chicago Mahogany, Dilla Thomas, for a powerful and personal tour of two of Chicago’s most culturally rich neighborhoods: Pilsen and Little Village.

Through stories of migration, resilience, and community activism, Dilla brings these neighborhoods to life—highlighting their role in shaping Chicago’s identity and their ongoing fight to preserve it.

This immersive experience blends history, storytelling, and local pride. We’ll wrap the evening with dinner at Los Comales, a beloved neighborhood spot known for its authentic Mexican tacos.

Leaves from the hotel lobby at 4:00pm.


SOLD OUT – The Power of Personal Narrative: A Workshop on Storytelling

Capacity: 20
Dinner: TBD

Join Anthony Moseley, three-time Emmy Award-winning Artistic Director of Collaboraction Theatre, for an interactive workshop on the art of storytelling.

Grounded in Anthony’s belief that “any piece of art is only as powerful and impactful as an artist’s willingness and ability to share,” this session will guide participants to tap into their personal experiences as the foundation for compelling, authentic narratives.

Through sharing his own artistic and personal journey, Anthony will model how vulnerability and truth can fuel powerful storytelling. Participants will be invited to take pen to paper and begin crafting stories that not only reflect their identity, but also shape their voice as leaders and changemakers.

Leaves from the hotel lobby at 4:00pm.


Stories on the Water: A Historic Kayak Tour of Chicago

Capacity: 20
Dinner: TacoRio

Glide through the heart of the city on a guided kayak tour along the Chicago River.

As you paddle through the iconic Riverwalk, expert guides will share captivating stories of the city’s history, architecture, and transformation—from early industry to modern innovation.

It’s an unforgettable way to experience Chicago from a fresh perspective. Afterward, we’ll head to TacoRio for casual riverside tacos and margaritas.

Leaves from the lobby at 3:45pm.

Scroll to top