Corporate Trivia for Chicagoland Teams, From the Loop to the Suburbs
A hosted trivia competition with stand-up comedy and game show rounds for company parties, conferences, sales kickoffs and team building across Chicago and the suburbs, led by former WGN and WIND radio personality Dan Deibert.
Call or text 262-333-0494 · We drive in, so there are no flights to book
Big events, big budgets, and half the room on their phones.
Chicago companies put real money into their parties and conference nights: the ballroom, the catering, the open bar. Then the entertainment turns out to be background music or a speaker nobody asked for, and people drift toward the exits or stay huddled with the same coworkers they see every day.
You don't need a bigger venue. You need something everybody in it wants to play.
A voice Chicago has heard before.
Dan Deibert's radio career included Chicago's WGN and WIND. Combine that with 30+ years as a clean stand-up comic and a lifelong trivia obsession, and you get a host who keeps a ballroom of sales reps, engineers and executives laughing and competing for the whole show.
HIP Trivia has hosted Chicago events for Discover, and Chicagoland teams at Cision and Associated Insurance have played too. Farm Credit Illinois brought the show to a regional meeting.
Also trusted by teams at Visa, OKTA and Northwestern Mutual.
Three steps to a better event.
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1
Tell us about it.
Your date, your Chicagoland venue and roughly how many people are coming.
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2
Get a custom plan.
A clear quote and suggested rounds built around your company and your crowd.
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3
Enjoy your own event.
We set up early, run about 90 minutes of play and hand out the bragging rights.
From McCormick Place to the O'Hare corridor.
Chicagoland has some of the biggest event spaces in the country, and a hosted game fills them well. HIP Trivia can set up for a conference night at McCormick Place, a party at Navy Pier, or a meeting at the Donald E. Stephens Convention Center in Rosemont or the Renaissance Schaumburg Convention Center Hotel. Downtown and O'Hare-area hotels, restaurant private rooms and your own office work just as well.
- We bring screens, sound and tablets, or work through your venue's AV crew
- We confirm load-in times and technical details with the venue ahead of time
- Guests can answer on our tablets or on their own phones
- Clean, HR-friendly comedy for clients, spouses and leadership in the same room
Chicagoland events we host
- Sales kickoffs and national meetings. A high-energy evening that brings regions and teams together after the business sessions.
- Company holiday parties. Something the whole company actually does together. See holiday party trivia.
- Conference and trade show evenings. A closing event for attendees, or a client reception your sponsors will remember.
- Client appreciation nights. A friendly competition that gives your guests and your team a reason to talk.
- Teams in more than one office. Bring remote staff in live with virtual trivia.
The event people are still talking about on Monday.
Picture the final scores going up, a winning team on its feet, and coworkers from different floors and different offices arguing over the one answer they almost had. That is what your budget should buy.
Skip the night everyone forgets by the time they hit the Kennedy. Book one they'll bring up for months.
What our clients say
Not Even Close to a 'Standard' Trivia Night!
Dan brought the fun and entertainment for sure. He did a phenomenal job at our (corporate) end of year party. The trivia was challenging which made it even more competitive between our teams. I thought our group would be too large to wrangle for trivia, however it went very smooth. No issues whatsoever. Dan keeps it going, has people engaged the entire time and is extremely accommodating. He has everything needed and the technology involved elevates your standard trivia game. I would absolutely recommend HIP Trivia for your next event… we certainly plan to have him back!
A great time was had by all!
We had such a positive experience with Hip Trivia! Dan was a pleasure to work with and a true professional! Dan was able to help us out on short notice, and scheduled a video chat with me to ensure planning was smooth. The event was a success and everyone had a great time – we will definitely be working with Dan again!
Laughter All Around!
This is the second time that our regional office has requested Dan as a performer for a company event. This time he brought his Hip Trivia to our team regional meeting. Dan is so organized, such a pleasure to work with and made our morning of trivia so much fun and a great success! I highly recommend that you hire Dan Deibert and his hilarious trivia show!
Chicago Corporate Trivia Questions
Can HIP Trivia set up at McCormick Place, Navy Pier or a convention hotel in Rosemont or Schaumburg?
Yes. Large convention venues suit a hosted game well, because every table competes at the same time instead of watching a few volunteers on stage. We can run our own sound, screens and tablets, or work through the venue's in-house AV and production crew. We handle the technical planning with the venue directly, so it's one less thing on your list.
Do you come into Chicago, or only the suburbs?
Both. We drive down from Waukesha, so there are no flights or airport pickups to arrange, whether your event is in the Loop, near O'Hare or out in the north and northwest suburbs. Dan also spent part of his radio career at Chicago's WGN and WIND.
Our event is at a downtown hotel. What do you need from the venue?
A power outlet and a table at the front of the room, plus a wired internet line for the host if one is available (we carry backups if not). If the hotel's AV team is running screens and sound, we plug into their setup and confirm the details with them ahead of time.
Will trivia work for a big sales kickoff or conference crowd?
Yes. Teams can play by table, by region or by department, and when a room is full of people who don't know each other yet, everyone can play on their own phone instead. Either way, scores update on the big screen after every question, so the whole room follows the race.
Can we add questions about Chicago or our company?
Absolutely. Add a round on Chicago, your company's history, your products or your leadership team, and we'll mix it with questions from our database of more than 100,000.
Our people are split between Chicago and other offices. Can everyone play?
Yes. Our virtual trivia show runs live over Zoom, Microsoft Teams, Webex, GoTo or RingCentral for groups up to 500 players, with nothing to download.
Bring HIP Trivia to your Chicagoland event.
Send us the date, the venue and a rough headcount, and we'll put together a custom quote. Holiday and kickoff season dates go first.
Get a Free QuotePrefer to talk? Call or text 262-333-0494 or email info@hiptrivia.com.
Looking for stand-up only? See Dan's corporate comedy for Chicago events.