“What’s the offsite going to cost?” is a question that arrives before any destination is chosen, from someone who wants a number, not a methodology. The honest answer — depends where we go — satisfies no one. The spreadsheet answer — two weeks of tab-by-tab flight searches across every origin — arrives after the decision has already hardened.
There’s a five-minute version. It’s accurate enough for a budget slide, and it has a useful side effect: it prices several destinations at once, which turns “can we afford an offsite” into “which offsite can we afford.”
The method
Minute 1 — headcount per airport. From the roster: how many people fly from each origin? A 20-person team might be SFO ×6, JFK ×5, ORD ×4, AUS ×3, DEN ×2. This table is 80% of the work and you only build it once per planning cycle.
Minutes 2–3 — get the intersection, with prices. Enter those airports in Midway. Every destination in the results is nonstop from all your origins, and the table shows the cheapest direct round-trip per origin for each destination — the exact per-seat numbers you’d otherwise open fifteen tabs to collect.
Minute 4 — multiply. For each candidate destination: sum of (cheapest fare per origin × headcount at that origin). For the 20-person team above, a Denver offsite might price out as 6×$250 + 5×$320 + 4×$210 + 3×$280 + 2×$0-ish (they drive) — call it $4,800.
Minute 5 — buffer. Multiply by 1.3. The cheapest fare is a floor, not a forecast: your dates are fixed, some people book late, some need the 9am instead of the 6am, and refundable corporate fares carry a premium. Thirty percent over the cheapest-fare baseline is the honest planning number. So: Denver ≈ $6,200 in airfare for 20 people. Done.
Run the same arithmetic down two or three candidate cities while the table is open — the whole point is that comparing destinations is now free.
Why the number swings: connections
Domestic nonstop round-trips mostly land in the $200–500 band. A connection doesn’t add a little — it typically adds 30–80% to the fare, plus four to six hours of travel time per person each way. This is the single biggest lever in offsite airfare, bigger than booking class, bigger than season.
Concretely: if 8 of your 20 people need connections to reach the trendy pick, that’s roughly $1,500–3,500 of extra airfare — and 60+ person-hours in airports, which you paid for in salary and day-one energy even though no invoice says so. It’s why this method starts from the nonstop intersection rather than from a destination wishlist: every city it prices already has the connection cost at zero for everyone.
When perfect coverage isn’t possible — the colleague in Boise, the teammate in Berlin — price their itineraries individually and add them as explicit line items. Two known connections chosen deliberately are a budgeting detail; twelve discovered at booking time are a budget overrun. The roster-to-shortlist method covers how to decide who connects.
Timing moves the floor
The per-seat floor you pulled is a snapshot, and it decays. Fares on popular offsite routes climb sharply inside six weeks of departure; the offsite pillar guide recommends locking flights 8–12 weeks out domestically, 12–16 internationally, and the savings from hitting that window usually exceed any other optimization on this page.
Day-of-week matters almost as much for offsites specifically, because everyone travels the same days. A Tuesday-to-Friday offsite books cheaper, flight by flight, than Thursday-to-Sunday — and midweek room blocks are cheaper too. If leadership is flexible on the pattern, run the estimate both ways; a two-day shift is often worth 15–20% of the whole flight line.
Going international: adjust two dials
The method survives contact with an international destination; only the constants change. The flight line roughly doubles — a $350 domestic average becomes $700–900 for Europe, somewhat less for Mexico and the Caribbean — and the buffer should grow from 30% to about 40%, because international fares are more volatile and rebooking is costlier when someone’s plans change.
Two line items appear that domestic estimates don’t have. Add a night of hotel for any destination more than three time zones away — day one after an eastbound red-eye is a half-day, and pretending otherwise just moves the cost into wasted session time. And add a passport-and-visa contingency: in any 30-person US team, assume at least one expedited passport renewal at ~$200. The international offsite guide covers which destinations keep these adjustments small — Mexico City and Toronto barely move the constants, Lisbon moves all of them.
What this estimate deliberately ignores
Knowing what the number isn’t keeps it defensible. It ignores seat class — if your travel policy upgrades long-haul flights, apply that policy’s multiplier yourself. It ignores the origin-fairness question (reimburse actuals vs. flat cap — a policy choice covered in the pillar’s logistics playbook), because the total is the same either way; only who absorbs variance changes. And it ignores ground transport, which belongs in the hotel-and-venue bucket.
It also deliberately uses the cheapest direct fare rather than the average fare as its base. That’s what makes the comparison between destinations honest: every candidate city is priced by the same rule, so the ranking is right even when the absolute numbers drift. The buffer absorbs the drift; the ranking drives the decision.
From estimate to slide
The deliverable this method produces, formatted for the meeting where it matters:
| Destination | Airfare (20 ppl, buffered) | Nonstop coverage | Worst flight |
|---|---|---|---|
| Denver | ~$6,200 | 20/20 | JFK, 4h17 |
| Nashville | ~$7,100 | 20/20 | SFO, 4h33 |
| San Diego | ~$8,300 | 18/20 | BOS, 6h12 |
Add hotel, venue, and meals — roughly $700/person for a two-night domestic offsite per the pillar’s budget breakdown — and you have the full per-person cost next to each city. Leadership picks between priced options; nobody falls in love with an unpriced postcard; the person who used to spend two weeks in flight-search tabs spends five minutes.
That’s the whole trick. The cluster hub has the destination-finding side of the process; start the priced search at app.midway.travel.