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Roaring 20’s Themed Events — Prohibition Speakeasy Energy
Full-service Roaring 20’s themed event productions for corporate parties, fundraisers, milestone celebrations, conference welcome parties, and casino party rentals in Chicago, IL and the Midwest. Chicago’s defining decade — the speakeasies, the jazz clubs, the gangsters, the flappers (Prohibition in the United States, Britannica) — brought back to your event.
- 5.0 653+ Reviews
- Serving IL, WI, IN, MI, MO, IA & OH
- Since 2011
- The Bash Rising Star
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The Roaring 20’s Aesthetic — Speakeasy, Not Society
Where Gatsby is West Egg old money, Roaring 20’s is Loop speakeasy. Same decade, different feeling.
The grammar:
The grammar:
Speakeasy entrance moment
Guests come through a hidden door, give a password, get a stamp. The arrival itself is part of the theme.
Period dress encouraged, not enforced
Roaring 20’s is more permissive than Gatsby; guests can show up in vest-and-tie or full flapper regalia and both fit.
Live jazz, blues, or ragtime
More upbeat, dance-floor-oriented, brass-forward than Gatsby jazz.
Period bar
Sazerac, Old Fashioned, gin rickey, French 75. Hand-printed period menu.
Low lighting with theatrical accents
Edison bulbs, candle clusters, table lamps. No ceiling lights.
Mob and flapper references
See the Al Capone, Flapper Girls, and Mobsters pages.
Charleston dance moment
A choreographed lesson during the program, with flapper performers leading — one of the highest-engagement moments at any Roaring 20’s event.
“The Roaring 20’s is the theme where the entrance moment matters more than anywhere else. A hidden door, a password, a stamp on the wrist — guests stop being event attendees and start being part of the scene. That five-minute moment shapes the rest of the night.”
— Jeff Durocher, President & CEO, U.S. Poker & Casino Parties
What’s Included in a Full Roaring 20’s Production
- Premium casino tables — blackjack, craps, poker, roulette in period-themed felts
- Professional dealers in vest-and-bowtie attire
- Speakeasy entrance setup — hidden-door framing, password card, hand stamp
- Branded playing cards and chips with 1920s-style motifs
- Live jazz/ragtime band or trio
- Period bar consultation — cocktail menu development with the venue’s bar team
- Themed decor — Edison bulbs, candle clusters, period-appropriate signage
- Optional add-ons: Al Capone impersonator, Mobster crew, Flapper Girls with Charleston lesson, Cigar Roller, 360 Photobooth with 20’s-themed overlay
Ready to Produce your Roaring 20’s Themed Events?
Quote in one business day. Serving corporate galas across Chicago, IL and the Midwest since 2011.
Pairs Well With
Best Venues for Roaring 20’s in Chicago
- Historic theaters and supper clubs in the Loop, River North, or Near North Side
- Speakeasy-style restaurants and lounges (several in River North and West Loop have built-in 1920s aesthetic)
- Hotel ballrooms with Edison-bulb lighting capability
- Loft and warehouse spaces with brick interior — surprisingly good for the underground-speakeasy feel
- Private rooms with low-lit, intimate footprints
Roaring 20’s for Corporate Events
- The speakeasy entrance is the single highest-impact corporate detail — brief invitation copy to include the password; brief door staff; make it part of the program
- Charleston dance lessons land at corporate events — pair flapper performers with a 10-minute teaching moment after dinner
- Branded chips, playing cards, table felts with subtle 20’s-style company integration
- Cigar roller + speakeasy theme = signature moment — particularly strong for VIP corporate, sales kickoffs, executive retreats
Frequently Asked Questions
Can you provide flapper performers and a Charleston lesson?
Yes — see the Flapper Girls page. The Charleston lesson is a popular add-on.
What’s the difference between Roaring 20’s and Gatsby?
Both are 1920s-themed. Gatsby is elegant/aspirational/old-money; Roaring 20’s is energetic/underground/speakeasy.
How much does a Roaring 20’s themed event cost?
A full production with casino tables, professional dealers, live jazz, speakeasy entrance, and themed decor for 75-100 guests starts around $8,000. Impersonators, cigar rollers, and custom-branded items are itemized.
How far in advance should I book?
Full Roaring 20’s production: 10-12 weeks ahead. Peak season (October-December) books out earlier.
Is the speakeasy entrance optional?
You can skip it, but it’s strongly recommended — the highest-impact moment of the theme.
Serving Chicago, IL & the Midwest
Based in Bensenville, IL — with delivery to the full Chicago metro and select cities across the Midwest.
- Chicago
- Bensenville
- Naperville
- Schaumburg
- Milwaukee, WI
- Detroit, MI
- Indianapolis, IN
- Cincinnati, OH
- + more
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