How many people can join The Chicago Outfit Espionage!?

The Chicago Outfit Espionage! works for groups of 15 to 1000 guests. Planning something bigger? Our client advisors can split larger teams across multiple sessions.

How long does The Chicago Outfit Espionage! last?

The full experience runs about 90 minutes, guided by your host from kickoff to wrap-up.

Is The Chicago Outfit Espionage! virtual or in person?

This experience takes place in person in Chicago. The exact meeting point is confirmed when you book.

How much does The Chicago Outfit Espionage! cost?

Pricing starts at $60 per person. Use the guest counter on this page to see your exact total instantly — no email or phone number required.

What if our plans change?

You can reschedule free up to 3 days before your event. The full cancellation policy on this page covers credits and cutoff dates.

How does booking work?

Pick your dates, customize your experience, and check out online — it takes about a minute. We confirm availability with your host right after checkout.

The Chicago Outfit Espionage! | Team Building in Chicago

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?

Office
Conference space
Local venue

World-class hosts
Actually fun — even for the skeptics
One price, everything handled
Backed by our Happiness Guarantee

Learn more about Originals

Energy 5/5 How energetic and dynamic is this activity?

Connection 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?

Welcome to the Speakeasy

10 minutes

Roles assigned, rules explained, mission begins.
Intelligence Gathering (Puzzles + Challenges)

70 minutes

Earn points, unlock clues, and identify the “rats.”
The Big Reveal + Wrap Up

10 minutes

Final accusations, identity reveal, outcome announced, and group photo.

Expert facilitation

90-minute experience led in person by our host.
Dedicated support crew

A co-host runs logistics, plus a VIP contact before, during, and after.
Flexible venue support

We fit the experience to your space and schedule.
All materials included

Game assets, props, and supplies.
Fully insured

COI, general liability, and workers' comp maintained by teambuilding.com.
Memorable team moments

We capture share-ready team photos.

Plans might change? No problem.

Reschedule free up to 3 days before your event, or cancel 7+ days out for a full account credit.

Full account credit	Cancel 7 or more days before the event date.
Guest count updates	Adjust guest count up to 7 days before the event (difference issued as account credit).
Free reschedule	Free reschedule up to 3 days before the event.
50% account credit	Cancel 3–6 days before the event.
No credit	Cancel within 3 days of the event.