The Itinerary Order Tax

Two cities have two orders; five have 120. The more orders there are, the less likely the first guess is the cheapest, and the more the miss costs. Trips of 2 cities paid an average of $59 a person; trips of 5 or more cities paid $140. With a few dozen trips in each group the steps between are not smooth yet; they firm up as trips accumulate.

Only airports with at least 10 trips in the data are ranked; a ranking of airports with three trips each would be noise. 4 qualify so far, and the list grows as more trips are planned.

A trip is placed in the region most of its cities are in. Trips through Europe paid the most on average ($117 a person) and trips through More than one region the least ($67). Europe trips also paid one most often, 74% of them.

3 cities (Buenos Aires, Sao Paulo, Punta Cana) from Hanoi, 1 traveler, December 2026. The order typed came to $3,435 a person in flights; the cheapest order of the same cities came to $2,489. That is $946 a person, or $946 for the group, for visiting the same places in a different sequence.

The trips above compare one typed order with the cheapest. For the 107 popular routes on the route pages, every order is priced from cached fares, so the full spread is known: between the cheapest and the most expensive order of the same cities, the median gap is $179 a person and the largest is $900 (Cairo, Nairobi, Johannesburg from New York). That is the worst case a guess can land on; the order tax above is what guesses actually land on.

Every trip is a plan someone made on Stopover: a home airport, two or more cities typed in some order, a window of dates, a range of nights per city and a number of travelers. The planner prices the typed order and every other order on dates that fit inside the window, per person, using the same fares for both, and keeps the cheapest. The order tax is the typed order’s price minus the cheapest order’s price, never below zero.

Prices are flights only, per person, in US dollars, from cached fares and from live searches where the plan ran them; they are the fares that were on sale when the plan ran, not booked tickets. Where a plan was ranked for balance of price and time rather than price alone, a cheaper order may have ranked below the ones kept, so the tax is, if anything, understated. Trips with one city (there is no order to choose), demonstration plans, plans the person stopped early, our own test trips, and trips where the typed order or the cheapest one was priced partly from an estimate rather than a quoted fare are left out. The same trip planned more than once counts once, the latest time.

The data holds the home airport, the cities, the month the window starts, how many days the window is, the number of travelers and the two prices. No names, accounts, exact dates, plan ids or fares by leg: a list of cities and a month is a trip, not a person. 405 finished plans were read for this version; 197 trips remain after the exclusions.

Download the dataset (CSV, 197 rows)

One row per trip: home, cities, region, travel month, window days, travelers, the typed order’s price per person, the cheapest order’s price per person, the gap, how many orders were kept, and the month the plan was made. Free to use and publish under CC BY 4.0 with a link to this page. It is rebuilt as trips accumulate; the date at the top is the date of the version you are reading.

To see what your own order costs, plan the trip: the plan shows the cheapest order and, when it differs, what the order you typed came to.