Choose Your Own Adventure – Spring 2023

Tue, Apr 25 
4:45pm – 9pm(ish)

Meant to expose you to the tapestry of the city, sessions range from E-Comm and social good with Bright Endeavors (an organization that provides critical services and coaching around housing, job training, and family support to young moms) to Deep Dish and a tour of Chicago’s Food Scene, as well as some old favorites. We hope that you can find something new that speaks to you, or give you the opportunity to experience your 2nd choice CYOA from the last time we were in Chicago.

Here’s what you need to know:

  • All sessions come with dinner (no $$ required by members)
  • Fri, Apr 7 is the deadline to register your session preferences (you rank your top 3)
  • Each session is assigned on a first-come, first-served basis
  • While we try to give you a break after the day’s meetings, some will be departing earlier. Please make note of the lobby departure times when making your choice.
  • Details below

Register for your top 3 choices here!

E-Comm and Social Good with Bright Endeavors ***SOLD OUT***

Capacity: 20
Dinner: TBD

Spend an evening with New Moms — an organization that provides critical services and coaching around housing, job training, and support for young families in Chicagoland.

In this adventure, you’ll get a behind-the-scenes look at their new 13,000 sq. ft. facility, and hear all about how they’re making an impact on the lives of young moms, their families, and the wider Chicago community.

And there’s more! During this adventure, you’ll get to dive into a candle-making experience with Bright Endeavors (a social enterprise of New Moms) and learn about their paid job training program. You’ll even hear about how they’ve transformed into a full e-commerce platform that supplies stores like Whole Foods and boutique shops across the country. So come learn about this incredible organization, and meet some of the amazing people who are involved.

You’ll then enjoy a casual dinner onsite which we’re still working to confirm.

This group departs from the Pendry lobby at 4:45pm.

Abracadabra at the Chicago Magic Lounge ***SOLD OUT***

Capacity: 20
Dinner: Boca Loca Cantina

Enter through the laundry and be transported out of the everyday and into a mysterious, magical experience. Members will be delighted by slights of hand from Chicago Magic Lounge’s talented company of seasoned magicians performing new routines and works they have perfected.

You’ll begin the evening with dinner on the patio at Boca Loca Cantina, about a 2 minute walk from the Chicago Magic Lounge. The Showcase starts with magic performed at your table while you and your fellow members enjoy craft cocktails. It ends with a stage show that is sure to deliver something you have never seen before.

Leaves from the Pendry lobby at 5:15pm.

Improv Comedy at Second City ***SOLD OUT***

Capacity: 20
Dinner: The VIG

If magic is not your thing, then maybe you’ll decide to spend the evening with the famous Second City.

The Second City is the world’s premiere comedy theatre offering the best in Chicago-style sketch and improv comedy, and has launched the careers of Tina Fey, Bill Murray, Stephen Colbert, Steve Carell and many, many others.

You’ll start with dinner at the VIG – a warehouse-style spot with gastropub eats, craft beer – before proceeding to the show.

Oh, and remember the first rule of Improv: if you laugh, then the performers are funny.

This group will depart from the Pendry lobby at 5:30pm.

The Black Star Project

Capacity: 20
Dinner: A taste of Bronzeville ft. Yassa, Pearl’s, and other local favorites!

The Black Star Project (TBSP) is excited to welcome CG Council members back again this year, for a discussion, neighborhood cleanup, and dinner. You will begin with a tour of Bronzeville — the South Side neighborhood where they are based — and will join Brother Sel, a local community member, in cleaning the alley behind the Black Star community center. Why?

The Bronzeville community follows the tenet, “if it takes a village to raise a child, a clean village does it better.” The US, and large cities as a whole, have developed a high tolerance for trash and debris, and as a direct result have discouraged economic development, generational wealth, property appreciation, encouraged crime, and impacted the resources coming into these communities.

So, you are there to learn, but also to help. After cleanup, you’ll head into the center for discussion, and finish the evening by enjoying dinner with a diverse group of youth, community leaders, and Black Star staff members – and doing a little light mentoring for the young people. The “Taste of Bronzeville” will be catered from multiple local restaurants – Yassa’s (Senegalese), Pearl’s (soul food), Ooh Wee It Is, Chicago’s Chicken and Waffles, Emeche’s and others – and TBSP will moderate a series of ice-breakers, activities, and discussion prompts.

Leaves from the Pendry lobby at 4:45pm.

Brews & Blues at Rosa’s Lounge

Capacity: 20
Dinner: Ørkenoy

Tony Mangiullo came to Chicago in 1978 after meeting Jr. Wells and Buddy Guy in Milan. Tony found the true spirit of the blues at South Side lounges like the legendary Theresa’s Lounge, and he opened Rosa’s in 1984 as a tribute to those cradles of blues tradition, and named it after his mother, Rosa, who had followed him to Chicago to help. It has been family owned and operated ever since.

Rosa’s was named “Chicago’s best blues club” by the New York Times and “…a blues mecca for true believers” by Rolling Stone. On this particular Tuesday, you’ll enjoy guitar riffs from Dave Herrero and friends

The adventure will begin just down the street with brews & dinner at Ørkenoy– a Nordic-inspired brewery with amazing food and ambiance. We’re not joking, Chef Ryan’s take on ribs and Caesar Salad will change your life.

Leaves from the Pendry lobby at 5:45pm.

The Hatchery – Food & Beverage Incubator

Capacity: 20
Dinner: Food from Dope Drip and cocktails from Present Tense

The Hatchery Chicago enables local entrepreneurs to build and grow successful food and beverage businesses, and provides job training and placement programs, which in turn create sustainable economic growth and new job opportunities.

Learn firsthand how these entrepreneurs are benefiting from launching from an incubator such as this, and not only taste some of their exceptional food, but also chat with them and learn about their experience to date in their fledgling business.

For dinner, you’ll enjoy food and beverages from two of the the entrepreneurs in their program, Dope Drip, an urban Puerto Rican inspired café, and Present Tense, a curated beverage experience.

Leaves from the Pendry lobby at 4:45pm.

Deep Roots to Deep Dish – Chicago’s Food Scene

Capacity: 20
Dinner: Food Tour

Join a local guide on this exploration of Chicago’s amazing food scene! The Loop is buzzing with activity, day and night, and your local guide will navigate you through the downtown streets straight to the vendors and restaurants they love most.

As you pass by places like the Chicago Riverwalk and take in the city’s awe-some architecture, you’ll get to grips with the evolution of the city as immigrants brought their culinary influence on The Windy City. You’ll get to know generations-owned shops and the origins behind Chicago’s most beloved street eats, all the while appreciating fresh ingredients sourced locally from midwestern farms.

Among the tastings that will add up to a full meal, you will get a taste of a local street food staple, perhaps the famous Chicago-style hot dog or Italian Beef, or another local favorite. A food tour of Chicago is not complete without a bite of the iconic deep-dish pizza, and we will top it off with a sweet treat with a meaningful connection to Chicago. By the end, you’ll have had the full Chicago foodie experience!

This group will depart from the Pendry lobby at 5:00pm.

Head to Head at the Emporium Arcade ***No Longer Available***

Capacity: 15
Dinner: Gus’s World Famous Fried Chicken

Want to duke it out with fellow members over air hockey? Maybe you’re the reigning Pinball champ in your family? Or you’re dying to play Miss PacMan? Then head to the Emporium Arcade, set in a vintage building in Chicago’s Fulton Market amidst murals from local artists, for a casual night of arcade games and handcrafted drinks. This is a no-frills, simple night of fun and games.

For dinner, you’ll head over to Gus’s World Famous Fried Chicken, where you’ll get your fingers GREASY enjoying their southern spicy fried chicken (a secret recipe that’s been going strong for over 60 years).

Leaves from the Pendry lobby at 5:30pm.

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