The best holiday party ideas for small teams in Chicago are built around an activity rather than a room rental: a private escape room followed by appetizers, a cooking class, a downtown walk with a warm stop at the end. A team of 6 to 20 is too small to justify buying out a venue and too big to fit around one dinner table, so the winning plan is an experience that already has a start, a finish and a reason to talk afterward. Book the date first; December calendars go fast.
Key takeaways
- Lead with an activity, then eat. Dinner-only parties for 15 people turn into three separate conversations.
- Decide the alcohol question early. A great party works either way, but the plan changes.
- A weekday afternoon slot is often easier to book, kinder to parents and commuters, and still feels like a treat.
- Popular December dates book out weeks or months in advance. Lock the date, then sort the details.
Why small teams get stuck planning a holiday party
Big companies have an events person and a budget line. Solo freelancers have a bar tab. The 6-to-20 team sits in the awkward middle: a restaurant will seat you, but you'll be split across two tables and the people at the far ends never talk. A venue buyout is overkill. A gift exchange in the conference room feels like a meeting with cookies.
The holiday party ideas for small teams in Chicago that actually work all share one trait: they start with "what do we do," not "where do we go." Once there's an activity, the venue question mostly answers itself.
Seven holiday party ideas for small teams in Chicago
1. A private escape room, then appetizers (drinks optional)
This is the plan we see work over and over, and not only because it's ours. A team of 6 or 7 fits one room, such as The Bank; a team of 12 to 20 splits into two or three rooms and races. Every booking at Fox in a Box is private, so you're never paired with strangers, and the 60-minute game gives the whole group one shared story to retell over food. Our event space handles the after-party, with appetizer and drink packages through local restaurant partners, and the drink part is entirely up to you. Details are on the team building page.
2. A Christkindlmarket wander with a reserved warm-up spot
The market typically runs from late November to Christmas Eve, and it's a classic for a reason. The trick for a group is to set a meeting point and a time, let people roam in twos and threes, then reconvene somewhere warm and reserved. Without the reserved spot you'll lose half the team to the crowd.
3. A cooking or cocktail class
Hands-on, naturally mixes people, and ends with something to eat. A mocktail version works just as well for teams that prefer to skip alcohol.
4. Lights, then dinner
Lincoln Park Zoo's winter lights or a loop through Millennium Park, followed by a reserved dinner. Low effort to organize, and good for teams with partners or out-of-town colleagues joining.
5. A weekday afternoon offsite
Block out the early afternoon on a Wednesday. Do an activity, eat early, send everyone home before rush hour. Nobody has to give up a Friday night, and remote colleagues who come in for the day can still catch their train.
6. A volunteer shift plus lunch
Pack meals, sort donations, then eat together. It's the right fit for teams that would rather do something useful than something fancy, and it needs no alcohol to feel like an occasion.
7. A game tournament in the office, done properly
Brackets, a trophy, a theme. The difference between a sad office party and a good one is whether someone actually planned it. If you want to bring the escape room to you, The Final Exam is our portable head-to-head game: we set it up at your office and teams of five play against teams of five.
With alcohol or without? Decide before you book
Both work. The mistake is leaving it vague and ending up with a plan where half the team expected one thing and got another.
- With: schedule the activity before the drinks. Escape rooms, classes and markets are more fun sober; the bar is more fun after a win.
- Without: pick an activity that does the social work drinks usually do. A competitive game, a shared task or a walk with a destination all count. Nobody misses the bar when they're arguing about who should have found the key in The Bunker.
If your team has been drifting apart over hybrid schedules, this is also the moment to fix it. Our post on coffee badging fixes your team will love has more on bringing a half-remote team back into the same room.
When to book (hint: now)
Here's the honest version. Because every room at Fox in a Box is private, a given time slot can only go to one group, and the most popular December dates and times book weeks, sometimes months, ahead. Teams that call early get their pick; teams that call in mid-December are choosing between what's left and January.
A sensible order of operations:
- Poll the team for two or three possible dates.
- Book the activity for the best one. The activity is the hardest thing to reschedule.
- Add food, drinks and anything else around it.
- Send the invite with a start time and a hard end time. People appreciate knowing when they can leave.
If someone can't make it, a gift card is a decent consolation prize, and a good small-team gift in general. And if the same plan keeps working, reuse it: our post on special occasions to celebrate with an escape room party covers birthdays, farewells and everything in between.
Frequently asked questions
How far ahead should a small team book a December holiday party?
As early as you can. The most popular December dates and times book out weeks and sometimes months ahead, so lock in your date first and sort details like food later.
Can we do a holiday party without alcohol and still have it feel like a party?
Absolutely. An activity-first plan such as an escape room followed by an appetizer spread gives people something to do and talk about, which is what most parties are missing anyway.
Is a weekday afternoon a good time for a team holiday party?
Often it's the best time. Nobody has to give up an evening, remote teammates can come in and still get home, and daytime slots are usually easier to book.
Got a team of 6 to 20 and a December date in mind? Send it through the quote form on our team building page and we'll put together rooms, food and timing that fit.
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