The way most companies pick an offsite city: someone senior suggests a place they liked, someone junior spends two weeks discovering what it costs to fly 35 people there, and by then the momentum is too strong to change course. The vibes were chosen first; the flights were an afterthought; the afterthought was 40% of the budget.
Here’s the reverse process. It takes about an hour, most of which is spreadsheet hygiene, and it ends with a shortlist nobody can argue with — because it was derived from where your people actually live.
Step 1: Turn your roster into airports (20 minutes)
Export the team roster with locations. Map each person to their real departure airport — the one they’d book, not the metro area. The distinctions matter: Oakland vs. SFO changes the nonstop map, Newark vs. JFK changes it more, and your teammate “in Colorado” who actually lives in Colorado Springs is a different problem than one in Denver.
Then collapse to a count per airport. A 40-person company typically produces something like: SFO ×9, JFK ×7, SEA ×5, AUS ×4, ORD ×4, BOS ×3, DEN ×2, and a tail of singles — Boise, Raleigh, Tucson, Berlin.
Two numbers to pull out of this table: your core airports (the fewest airports covering ~80% of headcount — usually four to six) and your tail (everyone else).
Step 2: Intersect the core (5 minutes)
Enter the core airports in Midway. The result is every destination with a nonstop flight from all of them, on a map and in a sortable table.
For a core of SFO, JFK, SEA, and AUS, that’s around 40 cities. Add Boston and Chicago and it’s still around 33. This is the fact that makes flight-first planning workable: even a six-airport core leaves you dozens of viable destinations, not three.
Don’t include the tail airports in the search — a single colleague in Boise shouldn’t veto the shortlist. The tail gets handled in step 4.
Step 3: Apply the boring filters (15 minutes)
Now — and only now — narrow by preference. Work down, in order:
Flight-time spread. Sort the table by flight time per origin. A city where one office flies 90 minutes and another flies six hours will generate quiet resentment; a spread under about three hours reads as fair. This is where geography does unintuitive things — Denver is over four hours from New York but under three from San Francisco, so a “central” city isn’t automatically a balanced one.
Season. October in Chicago is great; February in Chicago is a risk you’re choosing on behalf of 40 people. Filter the month you’re actually traveling — route maps shift seasonally, and a few destinations only clear the nonstop bar part of the year.
Ground cost and venue reality. Hotel-block rates and venue availability vary 2–3× across the surviving cities. The ranked list of US offsite cities covers the usual suspects’ trade-offs so you don’t rediscover Austin’s F1 blackout the hard way.
You should be at two or three finalists.
Step 4: Reconcile the tail (10 minutes)
Check each finalist against the tail airports. Some tails resolve for free — the Raleigh colleague has a nonstop to nearly any Eastern finalist. Some don’t, and that’s a decision, not a failure: a person connecting through Denver to reach Austin is a known, bounded cost.
The rule worth writing down: aim for 80–90% of headcount nonstop, and choose who connects on purpose. If a finalist forces connections on the same office that connected last time, rotate the burden or drop the finalist. Fairness across offsites matters more than perfection at any single one.
International tail — the colleague in Berlin or São Paulo — usually means a connection regardless of the US city you pick. If the international contingent is bigger than a person or two, read the international offsite guide before locking a domestic city; sometimes London or Mexico City beats any US option for total team travel time.
Step 5: Put a number on each finalist (10 minutes)
For each finalist, pull the cheapest direct round-trip per origin — Midway shows these in the table view — multiply by headcount per airport, and add 15% buffer. Two or three finalists, one airfare number each, one slide. The five-minute cost estimation guide walks through the arithmetic and its failure modes.
That slide ends the debate. “Denver: $14,200. Nashville: $16,900. San Diego: $19,400, and the Boston five fly six hours.” Leadership can pick on cost, on fairness, or on vibes — but for the first time they’re picking between fully-priced options instead of postcards.
What this replaces
The manual version of this process is real and grim: one browser tab per origin per candidate city, a spreadsheet nobody trusts, two weeks of elapsed time, and a decision made by fatigue. The flight-search sites can’t help — they price one origin at a time, because they’re built for a traveler, not a team.
An hour, start to finish. Roster to airports, airports to intersection, intersection to two or three priced finalists. The cluster hub explains why this ordering beats the listicle approach; the offsite pillar guide covers everything that happens after the city is chosen. Start the search at app.midway.travel — your roster is already the hard part, and it’s sitting in the HR system.