13 Best Chicago Holiday Party Entertainment Ideas to Make Your Celebration Extra Spirited!
The company holiday party should be so much more than free food and drinks — it’s a chance to celebrate, connect, and make memories with your coworkers outside the office. The right Chicago Holiday Party Entertainment easily transforms your event from an ordinary happy hour to an unforgettable night of festivities!
At WCF Events, we specialize in creating custom holiday party entertainment packages that combine fun, creativity, and convenience — all under one easy contract. From festive games and photo booths to live entertainment and charitable activities, we make holiday event planning simple, stress-free and full of holiday spirit.
Below, we’ve rounded up the Top 13 Trending Chicago Holiday Party Entertainment Ideas for 2025 to make your company event extra jolly!
🎄 1. Holiday Pub Trivia
Add friendly competition to your holiday celebration with Holiday Pub Trivia in Chicago! This interactive game brings coworkers together through laughter and lighthearted rivalry. From festive movie quotes to holiday traditions around the world, trivia keeps your team engaged and entertained.
Pro Tip: WCF Events offers the option to include custom trivia rounds to match your company culture — the perfect icebreaker for large groups or department parties.
🎁 2. Charitable Build Activity
Give back while you celebrate with a Charitable Build Activity. Whether your team builds bikes for kids, care packages for troops, or hygiene kits for shelters, this meaningful entertainment idea spreads holiday cheer across Chicago communities.
WCF’s CSR (Corporate Social Responsibility) events make it easy to combine giving, teamwork, and fun — all while supporting local charities.
🎅 3. Holiday Mini Games
Keep the energy high with a rotation of WCF’s Holiday MiniGames — a quick, festive activity that encourages togetherness and laughs. From video challenges to photo missions, this unique activity is perfect between cocktails, dinner, and dancing.
It is a great fit for any venue as an after dinner activity that doesn’t take up a lot of space.
📸 4. Photo Booth Fun
No Chicago holiday party is complete without a holiday photo booth! Add festive props, digital backdrops, and branded photo strips to give your guests instant keepsakes — and your company lasting visibility on social media.
WCF handles setup, props, and staffing, so your team’s only focus is striking a pose.
♣️ 5. Casino Night
Bring Vegas to Chicago with a Holiday Casino Night! Your guests test their luck at blackjack, roulette, and poker tables using play money — no real stakes, just high-energy fun.
Casino nights work perfectly for all types of corporate guests including beginners and skilled gamblers with a focus on teaching and having fun! Add a raffle for extra excitement at the end of the night!
🕹️ 6. Arcade Games & Virtual Reality
Level up your celebration with Arcade Games, Claw Machines, Virtual Reality experiences and more! From nostalgic skeeball machines to classic pop-a-shots, this entertainment trend is huge for 2025 and the options are endless.
Fun Fact: WCF even customizes claw machine prizes with your company’s logo or holiday giveaways — an engaging, one of a kind experience your employees will love.
🎶 7. Live Band or DJ
Music sets the tone for your party! Whether you choose a Chicago live band playing classic holiday hits or a DJ spinning dance favorites, live entertainment keeps the celebration lively and the dance floor packed.
WCF coordinates your entertainment preferences for a seamless experience.
🎭 8. Entertainers: Santa, Grinch, Carolers & More
Add a touch of magic to your Chicago holiday party with live entertainers! From Santa and Mrs. Claus to the Grinch, carolers, or even comedic emcees, professional performers help bring your theme to life and engage your guests in unforgettable ways.
Perfect for both formal and family-friendly events. Live entertainment adds instant holiday spirit to any setting and provides great photo ops for lasting memories!
🧊 9. Ice Carving
Dazzle your guests with an ice carving demonstration or hands on ice carving challenge. Ice carving is fun to watch but even more fun to try firsthand. Bringing ice sculpture to your event is a sure fire way to make the night special!
🎨 10. Holiday Craft Stations
Get creative with holiday craft stations, where guests decorate ornaments, make custom mugs, or build gingerbread houses. It’s a relaxed, hands-on way to connect while crafting a personal keepsake.
Craft stations are ideal for all ages, especially for companies inviting families to their Chicago holiday parties.
🎤 11. Holiday Karaoke
Turn up the fun with Holiday Karaoke! Let your team’s hidden talents shine with festive favorites and pop hits. Add a prize for “Best Performance” or “Most Festive Outfit” for even more laughs and engagement.
🧑🎄 12. Themed Costume or Ugly Sweater Contest
End the night on a high note with a Chicago-style ugly sweater or costume contest! Encourage creativity, snap some photos, and award prizes for the most outrageous or spirited look. It’s easy to organize and always a crowd favorite.
💻 13. Virtual Holiday Parties
Don’t forget your remote or hybrid teams! WCF also offers Virtual Holiday Party Entertainment that keeps teams connected no matter where they are.
From online trivia and digital scavenger hunts to virtual wine classes and holiday-themed games, these experiences bring festive fun to teams working from home.
Why Choose WCF Events for Your Chicago Holiday Party Entertainment?
With over 25 years of experience planning corporate events in Chicago and nationwide, WCF Events makes holiday party planning effortless. From entertainment to venues and logistics, we handle everything — so you don’t have to juggle multiple vendors.
Whether you’re envisioning a Casino Night downtown, a Charity Build event at your office, or a Virtual Holiday Party for remote teams, WCF customizes every detail to match your goals, budget, and guest count.
🎁 Ready to make your Chicago holiday party unforgettable? Contact WCF Events today to start planning your 2025 celebration!
