Event Recap: Chicagopalooza 2022

As the world navigates coming out of the pandemic, corporations are navigating the return to office policies, rebuilding company culture, trying to avoid ‘The Great Resignation,’ and are focused on ‘The Great Retention.’ For one of our Chicago-based clients, this meant bringing back a family-friendly retreat filled with 50+ activities over a 3-day weekend at the Grand Geneva Resort & Spa in Lake Geneva, WI.

Many companies are looking for ways to engage their team on a human level, recognizing the sacrifice families make when their partner/parent is off working (whether that be downtown in the office or tucked away in the basement ‘office’ these past couple of years), noting that many of their newer employees have never met their colleagues beyond the ‘Brady Bunch Bubbles’ of Zoom. For this company, it was clear that in order to re-humanize the employee experience and to thank them for their dedication and flexibility during the pandemic, coming together for a family-friendly weekend of fun, games, relaxation, and peer recognition was paramount to re-energizing the team while helping get the overall culture back on track.

The inaugural “Chicagopalooza” quickly became a thing of legend after the 2019 retreat, and due to COVID mitigations, there hasn’t been a retreat since. When we received the call asking to revive this epic (and award-winning) event, we were thrilled to take on the challenge while ensuring it wouldn’t be a complete ‘rinse and repeat’ – because that’s no fun for anyone!

Working in tandem with the client, our team of producers quickly began dreaming up new ways to engage the over 700 attendees of this year’s summer retreat. It’s important to note that for this event, and all live events at this point in time, there are a few key factors that make the planning process significantly different today than in previous years.

Every participant attends these events at varying levels of comfortability. For some, this might be the largest group of people they’ve been around in a couple of years. For others, this might be the first time staying in a hotel since the pandemic began. While some may be comfortable being indoors unmasked, others may only be willing to participate in outdoor activities. At the time of the event, children under the age of five were just beginning to be able to receive vaccines. Since COVID was (and remains) present and spreading, it was very important to keep the health and safety (both physical and mental) of all participants a top priority throughout the planning process.

With all of these challenges accepted, the Next Level Team and our teams of trusted event partners strategized, designed, organized (and sanitized) our way through another successful and epic weekend known as “Chicagopalooza!”

The Weekend Begins…

Friday afternoon, guests traveled from Chicago to the Grand Geneva Resort & Spa where they were welcomed by members of the event team dressed in bright green Chicagopalooza staff shirts. Throughout the weekend, our team of #eventprofs could be seen buzzing around the sprawling 1,300 acre campus preparing activities and events, all the while engaging with guests, answering their questions, and getting them excited for all of the fun (or relaxation) that we had in store for them! Due to a delightful midwestern summer rain, our team transitioned the Welcome Reception from the outdoor Pavilion overlooking one of the golf courses, to the conference center ballrooms indoors. Having this rain plan in place (just in case) allowed us to quickly pivot the Welcome Event providing many of the same activities without the muddy feet!

A large custom Welcome Sign (doubling as a photo backdrop) greeted guests upon arrival, while large colorful balloon installations, wine barrel tables with rustic floral, and café lights strung along the ceiling helped establish the theme. Wooden crates containing custom festival-inspired Chicagopalooza swag including baseball caps, bucket hats, fanny packs, sun glasses and more, were strategically placed throughout the event encouraging guests to explore the space while picking up fun items to help get them into the spirit of the retreat.

As guests made their way through the space, acoustic-inspired sounds from Colby & Co lured them towards the delicious smells of a summer gathering complete with Mediterranean and Grand Catalan buffets as well as the unmistakable aroma of toasted marshmallows coming from the s’mores station.

Of course, it wouldn’t be a family retreat without an exclusive kid’s area which included a buffet filled with all their favorite foods. There were also activities, like coloring all over the table tops, for them to engage in while their parents enjoyed the live music and chatting with their colleagues.

As the evening progressed, so did the party! A curated exclusive game room came to life just as dinner was coming to an end. We converted the Grand Ballroom into a game room inspired by the late ‘90’s complete with jewel-tone and sequined linen on the tables, Penelope Green sofas with fuchsia pillows and bright blue ottomans for soft seating lounges. Club-inspired silver bars provided themed libations while bright pink and blue uplighting transitioned this traditional meeting space into the ultimate game room. In addition to games like Pool, Pop-a-Shot, Table Tennis, Foosball, Darts, Air Hockey, Shuffleboard, Giant Jenga and Connect Four, guests were ultimately entertained by their colleagues with Live Band Karaoke! The room was alive the rest of the night by guests of all ages! (#NLEDbts: while some of the younger guests ‘threw it back’ with songs by Miley Cyrus – it was impressive how some 90’s hits had that room on its feet!)

The Weekend Continues…

With over 50 activities in only 28 (waking) hours, it was no surprise our early risers decided to get a head start on the day with a zen-like early morning poolside yoga session, while others engaged in a brisk morning 5k run. The kiddos also got a chance to showcase their speed with a 1-Miler. (#NLEDbts: we all got the warm fuzzies when we learned that Cory, our Vice President, led the kids in a quick warmup and stretch before counting down on the megaphone. Awwww!)

With so many activities to choose from, it was important to build space for guests to kick back and relax or hang out at a more leisurely pace. The (air conditioned) Game Room was available to guests throughout the day, and the Recreation Center was exclusively booked for guests to participate in Rock Climbing, Pickle Ball, Tennis, and Basketball. For the golfers in the group, they had the chance to golf on two of Wisconsin’s premier golf courses (which just happen to be on property). A friendly (and sometimes competitive) sand volleyball match kept things heated amongst colleagues while a family-focused water balloon toss cooled off the kiddos in the afternoon sun.

The Chicagopalooza Runway Festival… 

As the late afternoon sun lingered overhead, the highly anticipated Runway Festival was about to begin. This exclusive street-festival inspired event takes place on the private airport runway located in the heart of the Grand Geneva’s campus. This active runway gets shut down for a week in order to create this evening filled with live music, games, food, festival activities and more!

As guests arrived via shuttles, cars, and on foot; colorful 10’ tall custom flags directed them into the festival grounds. Multiple food trucks lined up serving Empanadas, Egg Rolls, Italian Sausages, Meatball Subs, Woodfired Pizzas, Funnel Cakes, Deep Fried Oreos, Sno-Cones, CottonCandy, Specialty Popsicles (and more) catching guest’s attention immediately as they entered the grounds. The aroma of grilled summertime staples like BBQ, Burgers, and Sausages filled the air. Beverage tents offered a range of refreshing beverages including thematic cocktails, mocktails, and local brews like New Glarus’s Spotted Cow.

There were games and activities for kids and adults alike all throughout the runway! In the Kiddiepalooza area there were activity stations with Bubble Wands, Face Painting, Sand Art, Coloring, and (incredible) Balloon Art. Yard games including Big Birdie Golf, Bags, Spike Ball, Ladder Golf, Beersbee, Bocce Ball, Hula Hoops and more kept people engaged in some friendly competition. If yard games weren’t your thing, there were also three different bouncy houses for kids of all ages to enjoy.

Multiple photo opportunities were made available as well. Guests could jump in and out of a Vintage Yellow Bus trying on various hats, playing with instruments and props, resulting in the quintessential (awkwardly funny and delightfully whimsical) photo strip. An insta-worthy backdrop was created for guests to strike the perfect pose(s) for digital black and white photos. Wandering ‘Photo Roamers’ (with ring lights for balanced illumination both day and night) captured the perfect candid moments, as well as impromptu group shots, which were immediately forwarded for guests to populate their social media feed.

A 42-foot wide custom branded stage anchored one end of the runway. It was the backdrop for the highly anticipated Employee Awards Program and home to the five different live musical acts featured throughout the night. A family-focused performance by Grammy Award winning artist, Nanny Nikki kicked things off. (#NLEDbts: her energy was so contagious she had the entire tech team performing “Head, Shoulders, Knees and Toes” from the tech booth – there may be video evidence of this…)Trippin’ Billies: A Dave Matthews Tribute Band then provided chill vibes through the late afternoon sun.

Employees were recognized by leadership for their impressive achievements and contributions to the company in front of their families and colleagues while their photos were displayed on a giant 24’x12’ video wall that stood immediately next to the stage.

Following the Awards Program, Run Forest Run: A 90’s Cover Band kept the energy up while the sun went down. As night fell over the runway, Shout Out Band lit up the stage while a curated 15-minute long fireworks display lit up the summer night sky. DJ JaxxSway then took to the stage and kept the beat going late into the night.

All good times must come to an end… 

For many, Sunday morning came all too soon, despite the delicious brunch they were offered before they hit the road. Perhaps they had too much fun doing Live Band Karaoke, wanted to get a better time in the 5K or wanted a rematch on one of the other golf courses; or maybe they didn’t get to play that round of Mini Golf or splash around at the waterpark, maybe they missed the funnel cake because they found themselves on the runway dancing late into the night. We like to think it’s because it was just so much fun they didn’t want it to end.

As guests boarded the shuttles back to Chicago, or drove out of the parking lot honking their horns and waving goodbye, it was clear they had just experienced something special. They got to have real moments with their colleagues and their families, creating memories of fun, playing games, and endless laughter. They got to show up as their multi-faceted, talented, competitive, relaxed, engaged, authentic selves amongst peers.

Events don’t become legendary just because they exist; they become legendary because of how they made you feel. Sound familiar?

“People will forget what you said, people will forget what you did, but people will never forget how you made them feel.”  – Maya Angelou

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