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Adding the “Roar” to your 20s Event

Roarin’ 20s event

The Roarin’ 20s Have Finally Arrived

With the Covid-19 Pandemic largely behind us, we are excited to see the return of live events, especially those for corporate clients starting to return. While we know offices and work environments will never fully return to the way things were before the pandemic, we are excited to already be hearing the buzz about corporate holiday parties. If you are looking for a theme to ‘sink your teeth into,’ we finally have an excuse to celebrate the 2020s in style with a Roarin’ 20s event. We’ve broken down a few key items that will have your guests doing the Charleston all night long.

Invite Your Guests In Style

Art Deco Elements

Generating some buzz and excitement for an event starts with the invitation. Whether electronic or mailed, an easy way to start to sell the theme is by incorporating Art Deco elements that evoke that 20s style and feel.

Passwords To Enter

The invitations can also include a secret password that guests will have to use to enter the event. Adding some mystery or exclusivity to your invitation is a great way to start to get your guests into character.

Choose A Venue That Sets The Stage

Chicago Venue With 20s Style

Chicago Venues With 20s Style

We are spoiled in Chicago by having so many venues that have direct ties to the 1920s. From converted warehouses to historical landmarks, and everything in between, the challenge of choosing a venue to fit your needs is not made challenging by too few options, but rather too many. We’ve created a guide to venues around town that are perfect for a 20s party here.

A Secret Entrance

Some venues like Morgan Manufacturing, Bridgeport Art Center, and Union Station would easily allow guests to enter through a secret entrance. Encouraging your guests to get into character by entering with the password that was provided in their invitation is a great way to set the stage and get the party started.

Sell The Speakeasy

Flappers & Zoot Suits

Encouraging your guests to come dressed in their best 1920s attire is a great way to carry the theme throughout the events. We are always surprised how excited guests are to dress up, and how much a costume can elevate participation in the event. Even for those who opt for something on the safer side, adding a prop table with pearls, fedoras, fake mustaches, and a few head-dresses can encourage guests to get into character.

Classic Cocktails

Classic Cocktails

Bathtub Gin has come a long way since the 1920s, but prohibition-era cocktails are still being reimagined and remade in the most trendy bars around town. Welcoming your guests with a classic French 75, a mix of champagne, lemon, and Gin is a great way to get your guests to let loose. Incorporating a specialty cocktail list with a few 1920s inspired drinks is a great way to carry the theme through food and beverage.

Add Some Camp With a Few Guest Appearances

Entrance Entertainment

A great way to greet guests as they enter the venus is by incorporating a few well-placed character performers. From Flappers with feather fans to a couple swing dancing, a few performers can help elevate the energy as guests explore the space.

Roaming Performers

Adding a few roaming gangsters, an Al Capone impersonator, or a few roaming flappers to pose for a picture or interact with the guests can keep the theme alive throughout the event.

Activations, Cigars Rolling, & Photobooths


Adding an activation to your event can be a moment to add variety to the flow, and allow guests a moment to create or receive a takeaway. For a 20s themed event there is quite a lengthy list of activation you can incorporate but here is a list of some of our favorites:

  • Cigar Rolling: this isn’t just because it’s a service we provide, it can also be a great 5-10 minute experience that incorporates branding and cultivates conversation. If your venue has an outdoor courtyard, it may be worth creating an outdoor smoking lounge.

  • Photo Booths: The traditional photo booth has come a long way over the past years. There are now roaming photobooths, gif photo booths, step & repeats that incorporate elaborate backdrops, photo booths that are fully integrated into social media. Adding some 20s themed props and making the photo op an experience is a great way to create lasting memories

  • Swing Dance Lessons: If you are springing for a big band to create an authentic 20s feel, what better way to get your guests dancing than with a swing dance instructor that can show some era-based dance moves.

  • Champagne Tower: What is more elaborate than a tower of champagne flutes? If you are working with a decor partner, creating a visual focal in your space with a champagne tower is a great way to elevate your 20s look, and provide a moment of celebration.


Don’t forget the “Gambling” at your 20s event

Last but certainly not least, what is any speakeasy without a little “gambling”. Adding a fundraising element into your corporate event by integrating Blackjack, Poker, Roulette and Craps is a great way to further engage your guests, add some authentic speakeasy experience, and raise some money for a good cause.

Guests can receive a voucher at checking that can be worth a dedicated amount of “funny money” to use throughout the evening. Upon cashing in, the top three earners can select a charity of their choice to make a press-designated contribution to.

If prizes are more your style, the same concept can be done awarding the top three earners with something special.

We hope reading through the ideas here will provide some inspiration and insights on planning your next 20s event. U.S. Poker Casino Party is happy to help coordinate and help you source the right vendor team to produce an unforgettable evening.


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