Book with Confidence
Verified Reviews
No Markups
Flexible Bookings
Secure Payments
Happiness Guarantee

The Chicago Outfit Espionage!

A Prohibition-era Chicago social deduction experience where your crew solves puzzles, completes missions, and hunts for undercover agents.

Host: teambuilding.com · 183 active listings ·
4.98
· 80,587 reviews

How it works

Gear up for a team-building experience like no other: The Chicago Outfit Espionage, a mobster-themed social deduction game set in Chicago during the roaring 1920s. Picture the tension of a speakeasy, the thrill of a covert mission, and the satisfying click of a puzzle snapping into place. Your group will step into a world of Prohibition-era intrigue where loyalty is everything… and someone at the table may be working for the feds.

Led by our world-class hosts, each participant is assigned a unique secret role within the syndicate. Will you be a loyal Smuggler protecting the operation? A savvy Strategist calling the shots? Or a crafty Undercover Officer quietly sabotaging the crew from within? Your objective is clear: work together to keep the Outfit in control and uncover the “rats” before the raid hits.

This experience blends high-energy puzzles, bootlegging challenges, and strategic maneuvers with classic social deduction mechanics. Teams will decode clues, crack combinations, unlock contraband, and complete missions to earn points, while simultaneously watching for suspicious behavior, misdirection, and subtle sabotage. It’s a unique mix of collaboration and calculated distrust that forces teams to communicate clearly, think critically, and make decisions under uncertainty.

As the stakes rise, your team will sharpen their observation skills, strengthen persuasion and consensus-building, and practice trust under pressure, mirroring real workplace dynamics where information can be incomplete and alignment matters. The finale delivers a satisfying payoff: final accusations, a dramatic reveal, and the ultimate question: did your crew outsmart the feds, or did the double agents bring the Outfit down from the inside?

This experience comes to you

The Chicago Outfit Espionage! can run virtually anywhere—your office, a conference venue, or a nearby space that suits your team.

Pick the setting that works best for your team and our hosts will take care of the rest.

Relax, it's an Original

Intentional and fun team building by the team that has delivered on experiences for over 1 million participants.

  • Signature experience

    Built and continuously improved by our in-house team.

  • Live, expert facilitation

    Professional hosts keep energy high and groups engaged.

  • Proven results at scale

    Trusted by thousands of teams, from startups to the Fortune 100.

Core Ratings

Key characteristics of this experience.

Energy Level 5/5 How energetic and dynamic is this activity?
Icebreaker 2/5 How well does this help people get to know each other?
Bonding 2/5 How well does this build team relationships?
Creativity 3/5 How much creative thinking and expression is required?
Learning 3/5 How much new knowledge or skills are gained?
Ratings are based on expert review, AI assist, and community sentiment.

Agenda

A step-by-step look at how the experience unfolds.

Total time: 90 minutes
  1. Welcome to the Speakeasy
    10 minutes
    Roles assigned, rules explained, mission begins.
  2. Intelligence Gathering (Puzzles + Challenges)
    70 minutes
    Earn points, unlock clues, and identify the “rats.”
  3. The Big Reveal + Wrap Up
    10 minutes
    Final accusations, identity reveal, outcome announced, and group photo.

Included with your booking

Everything you need for a seamless team experience is part of the package.

  • Expert facilitation

    90 minutes live session led by a teambuilding.com host.

  • Flexible venue support

    We collaborate on logistics so the experience fits your space and schedule.

  • All materials included

    Game assets, props, and activity supplies are bundled into one booking.

  • Memorable team moments

    We capture share-ready team photos so you can relive the highlights.

You should know

Key details to share with your team before event day.

  • You can book for an estimated number of guests and update it up to 7 days before your event. Added guests are invoiced at the per-person rate and removed guests receive credits.

What teams say about The Chicago Outfit Espionage!

Real reviews from organizers and participants who booked this experience.

Overall sentiment

N/A / 5.0 rating (0 reviews)
Verified
  • 5
    0% 0
  • 4
    0% 0
  • 3
    0% 0
  • 2
    0% 0
  • 1
    0% 0
Filter reviews

Choose how to sort the latest feedback.

Team building starts here