If your remote team is coming to Chicago for a few days, spend one afternoon on something that gets people eating, walking, and talking at the same time. That is the whole trick. The activities that actually bond a distributed team are the ones where nobody has to be good at anything, everybody gets fed, and the conversation happens sideways instead of across a conference table.
I'm Jonathan Porter. I run Chicago Pizza Tours, and I plan afternoons like this most weeks of the year for teams flying in from all over. So this is the honest local's version, not a listicle written by someone who has never had to keep 40 people happy between 1pm and 4pm.
The real problem with a remote onsite
Your people see each other on a screen eleven months a year. Now they're in the same city for 48 hours, and someone (an office manager, an executive assistant, a people ops lead, or the engineering manager who drew the short straw) has to fill the non-meeting hours with something better than "drinks at the hotel bar."
That's harder than it sounds, because the activity has to do four jobs at once:
- Bond people who barely know each other in person.
- Feed everyone, including the vegetarian, the gluten-free person, and the one who "isn't that hungry" and then eats the most.
- Show off the city to people who flew in and have never seen it.
- Include everybody, no matter their age, mobility, or willingness to look silly in front of coworkers.
Most "team building" fails at least one of those four. Here is how the popular options really stack up.
The honest comparison
| Activity | Bonds people | Feeds everyone | Shows the city | Works for all |
|---|---|---|---|---|
| Escape room | Sort of (one loud person leads) | No | No | No |
| Axe throwing | A little | Snacks only | No | Not for everyone |
| Boat architecture tour | Not really | No | Yes | Yes |
| Sit-down group dinner | Only your two neighbors | Yes | No | Yes |
| Cooking class | Yes | Yes | No | Mostly |
| Food or pizza tour | Yes | Yes | Yes | Yes |
Nothing on that list is a bad time. But if you only get one afternoon, you want the row that checks all four boxes, because a remote onsite is not the moment to gamble on axe accuracy.
A few ideas that genuinely work in Chicago
I'm not going to pretend pizza is the only answer. A real list is more useful than a sales pitch, so here's one.
- A walking or bus food tour. People eat, move, and talk without being forced to. The walking builds in a natural small-group shuffle, which is exactly what you want for folks who only know each other from Slack.
- The Riverwalk plus an architecture boat tour. Beautiful, easy, and great for first-timers. Just know that everyone faces the same direction and doesn't talk much, so pair it with something social.
- A cooking or hands-on class. Solid bonding if your group is under about 20 and nobody has a knife-safety concern.
- A neighborhood scavenger hunt. Fun and competitive, but it lives and dies on the weather and how into it your team actually is.
- A pizza tour. My bias is right there on the label, so take it with a grain of salt. But it's built for this exact situation, which is the next section.
Why a pizza tour is almost cheating for this
An onsite afternoon has a time problem. Every hour your people are together in person is expensive, so the activity has to earn its slot. A pizza tour quietly does three things in one three-hour block. You see the city, you eat a real Chicago meal, and your team bonds while doing both, with zero skill required. Eating is the great equalizer. The junior hire and the VP are the same person in front of a deep dish.
The logistics are the part planners actually care about, so plainly: I take groups of 15 to 100 (larger with coordination), the food is pre-ordered and waiting so nobody stands around, dietary restrictions are handled ahead of time, and you get one receipt for the whole thing to hand to accounting. If you want the full breakdown of how a private team outing works, I put it here: corporate and team outings.
And yes, we've been on Wheel of Fortune, WGN, and the Travel Channel, among others. I only mention it because "the thing your team did in Chicago got featured on Wheel of Fortune" is a fun line for the person who planned it.
How to actually pick
If your onsite runs Monday through Thursday and you have a free afternoon, book the thing that feeds people and moves them through the city. If your team is small and loves to cook, do the class. If half your group flew in for the first time, lean toward anything that shows off Chicago. And if you want the version that does all of it at once, that's the tour.
Reach out to plan a team outing or check our weekend tour availability. All you have to do is get your people here hungry.
Common questions
The one that feeds everyone, moves through the city, and needs no special skill, so people bond by accident. A walking food tour or a pizza tour fits that better than an escape room or a sit-down dinner, because everyone participates equally.
Plan for about three hours in the afternoon. That is long enough to actually bond and see part of the city, and short enough to leave room for dinner or a working session the same day.
I take groups of 15 to 100 on a private pizza tour, and larger groups with some advance coordination. Tell me your headcount and I will tell you what is possible.
That is handled before the day starts. I sort out vegetarian, gluten free, and most restrictions in advance so nobody is standing there with nothing to eat.
Earlier than you think. Private afternoon slots on weekdays fill up, especially in the busy months, so reserve the date as soon as your onsite is on the calendar.
