Office Holiday Party Ideas & Entertainment in Chicago

Skip the coat-check line. We bring the host, the game or the paint kits to your office in the Loop, River North, Fulton Market or wherever your team sits, set up, clean up, and nobody steps outside.

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Holiday party formats we bring to Chicago offices

Each runs about an hour with a live host; pair two for a full party. Running it yourself? Try our holiday party games for work.

Prices and December booking dates

List prices for Chicago, the same numbers the booking page quotes, and when to book for December.

Format30 guests60 guests100 guests150 guests
Feud Night$1,750$2,200$2,200$2,650
Music Bingo$1,750$2,200$2,200$2,650
Team Trivia$1,750$2,200$2,200$2,650
Blitz-Speed Trivia$1,750$2,200$2,200$2,650
Canvas Painting$2,400$4,050$6,250$9,000
Watercolor Card Decorating$2,310$3,870$5,950$8,550

Food, drinks and the room are yours. Booking two formats? Ask for both in one quote.

For a party on Thursday, Dec 17, book by

Our standard lead times: 2 weeks for hosted games, 3 for painting, 4 for custom branding or questions.

Hosted games (2 weeks ahead)
Dec 3
Painting workshops (3 weeks ahead)
Nov 26
Custom branding or questions (4 weeks ahead)
Nov 19

A sample two-hour party in Chicago

A Wednesday, 11:30 am to 1:30 pm, 40 guests. A lunch party: full turnout from the people who ride Metra or drive in, and everyone still catches their usual train home.

  1. Before lunch

    Tables set for painting

    The host lays out watercolor paper, paints, brushes and aprons. You need water access and a few trash cans.

  2. 11:30 am

    Watercolor Card Decorating

    Lunch lands as the host starts the first wash. People eat while the paint dries and finish a set of four cards.

  3. 12:30 pm

    Sign a card, swap seats

    Everyone signs one card for a teammate, then tables regroup into trivia teams.

  4. 12:35 pm

    Team Trivia

    Picture rounds, bonus rounds and a wager finale. Captains submit answers by QR code.

  5. 1:35 pm

    Winners crowned

    Back at desks by mid-afternoon, with a card to give and a reason to talk about it.

At 40 guests: Watercolor Card Decorating $2,830 + Team Trivia $1,750 = $4,580 at list prices.

At your office or venue

What we bring to your Chicago office, what we need from you, and how the price grows with headcount. We handle setup and cleanup.

Hosted games

Feud Night · Music Bingo · Team Trivia · Blitz-Speed Trivia

We bring

  • Live support
  • A professional host
  • Printed bingo cards and daubers (Music Bingo)

You provide

  • Tables and chairs for every guest
  • A TV or projector with an HDMI cable
  • Phones to scan a QR code (or a web browser) (Feud Night and Team Trivia)

Space: One room where every table can see the screen. Teams sit together, so a conference room, pantry or open floor all work.

Headcount and price: Feud Night, Music Bingo, Team Trivia and Blitz-Speed Trivia are $1,750 for up to 50 guests, plus $450 for each additional 50.

Painting workshops

Canvas Painting · Watercolor Card Decorating

We bring

  • A professional host
  • Setup
  • Cleanup
  • Every painting supply

You provide

  • Water access
  • Tables and chairs for every guest
  • Trash cans (Canvas Painting)

Space: Table space for each painter and a sink or water source nearby. Aprons come in the kit.

Headcount and price: Canvas Painting is $55 a person plus a $750 base fee. Watercolor Card Decorating is $52 a person plus a $750 base fee.

Planning a December party in Chicago

Whether your team sits in the Loop, Fulton Market or a suburban campus, these are the Chicago details that shape a December party.

  1. Let the weather decide the venue

    December in Chicago is cold and windy, and it can snow. A party in your own office means nobody walks between venues and no coats end up in a heap. Clear a rack or a spare room for coats.

  2. Lunch beats late for commuters

    Teams that ride Metra or drive in from the suburbs often prefer a long lunch to an evening party. You get everyone, and nobody watches the clock for the last good train.

  3. Downtown is busier in December

    Holiday markets, Michigan Avenue shoppers and theater crowds slow down the Loop on December evenings. Plan extra travel time for anyone coming from another office.

  4. Decide your snow-day rule early

    Agree internally who makes the call if a storm closes the office, by when, and whether you would move the party or run it with whoever is in. Bring it to your planning call with us.

Want ideas beyond our formats? Read 45 office holiday party ideas.

Chicago holiday party questions

How much does office holiday party entertainment cost in Chicago?

Feud Night, Music Bingo, Team Trivia and Blitz-Speed Trivia are $1,750 for up to 50 guests, plus $450 for each additional 50. Canvas Painting is $55 a person plus a $750 base fee. Watercolor Card Decorating is $52 a person plus a $750 base fee. That covers the host, the game and, for the painting formats, every supply. Food, drinks and the room are yours to arrange.

How far ahead should we book a December holiday party in Chicago?

Book hosted games at least 2 weeks ahead and painting workshops at least 3 weeks ahead; branding or custom questions need 4 weeks. For Thursday, Dec 17, that means booking games by Dec 3 and painting by Nov 26. If your date is sooner than that, ask us; we confirm what we can run in your plan.

Can we do a lunch holiday party instead of an evening one in Chicago?

Yes. Every format runs an hour, so two of them fit a long lunch. Watercolor cards pair well with food on the table, and a trivia game after keeps the energy up into the afternoon.

What if it snows on the day of our Chicago party?

Set your snow-day rule before December: who decides, by when, and whether you move the date or go ahead with whoever is in. Raise it on your planning call so we plan around the same rule.

What do we need to provide for a party at our office?

A room with tables and chairs, a TV or projector with an HDMI cable for the games, and phones to scan a QR code. The painting formats also need water access and trash cans. We bring the host, the game, the scoring and, for painting, every supply, and we handle setup and cleanup.

What if more people show up than we planned for?

Give us your best headcount estimate; we use it to plan hosts and support. We can take extra guests on the day, and if attendance is well over your estimate we invoice the difference.

Can remote employees join the party?

The in-person formats are built for people in the room. For remote staff, book a virtual holiday party on Zoom (Microsoft Teams, Google Meet or Webex on request) on another day, or run one for the whole company.

Can we add holiday gifts for the team?

Yes. Pair the party with corporate holiday gifts shipped to each person, which also covers anyone who can't make it to the office that day.

More holiday party planning

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