The Cheapest Hotel Order Isn't Always the Cheapest Trip: A Real Colombia Case Study
Comparing hotels alone across six possible city orders pointed to a clear $46 winner. Adding flights back in didn't flip the answer — but it cut the advantage nearly in half. Here's why hotel-only comparisons are a hypothesis, not the answer.
Meta description: Comparing hotels alone across a 3-city Colombia trip pointed to one clear cheapest order. Adding flights back in didn't flip the answer — but it cut the advantage nearly in half. Here's how to compare the total cost of a multi-city trip properly, and how FortripAI's Optimization Agent runs it automatically.
Quick answer: comparing hotel cost alone across different city orders is not the same as comparing the total trip cost. International flight prices can differ by hundreds of dollars depending on which city you fly into or out of, which means the order that looks cheapest on hotels alone isn't always the order that's cheapest once flights are added back in — sometimes it still wins, just by a smaller margin than it appeared to.
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Same trip, same cities — but move the departure date and one October flight window swings $142, while a single hotel's date slot swings $333. Worse, four of six possible city orders weren't even bookable. Here's why flights and hotels have to be priced together, and what happens when they aren't.
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The Setup: 3 Fixed Hotels, 3 Cities, 6 Possible Orders
A 10-day Colombia trip from Toronto: 3 nights at a Bogotá hotel, 4 nights at a Medellín hotel, 4 nights at a Cartagena hotel — same three properties, same total nights, the only open question being which city to visit first, second, and third. With three fixed cities, that's six possible orderings.
Step 1: Compare Hotels Alone — Where Most People Stop
Pricing the hotel stays across all six orderings turned up a real spread:
Order
Hotel total
Medellín → Bogotá → Cartagena
$1,862.77
Bogotá → Medellín → Cartagena
$1,908.39
Medellín → Cartagena → Bogotá
$1,996
Bogotá → Cartagena → Medellín
$2,022
Cartagena → Bogotá → Medellín
$2,022
Cartagena → Medellín → Bogotá
$2,041
Based on hotels alone, Medellín-first looks like the clear winner — about $46 cheaper than the more geographically obvious Bogotá-first order, and up to $178 cheaper than the most expensive sequence. This is exactly where most people stop comparing: hotels are the easiest thing to re-price for six different date windows, so the "cheapest order" conclusion usually gets drawn from hotels alone.
Step 2: Add Flights, and the Advantage Shrinks
Flights don't move in the same direction as hotels — and they don't move by the same amount.
International flights aren't priced the same from every city. Toronto's connections into Colombia are strongest into Bogotá — it's the country's main hub for this route. Flying into or out of Medellín or Cartagena instead carries its own fare structure, sometimes cheaper, sometimes not, but never assumed to track the hotel savings.
Domestic legs between the three cities add a smaller but real layer on top — three separate short flights, each priced independently, stacking onto whichever international entry and exit points you chose.
Once both were priced across all six orders:
Order
Flights
Hotels
Total
Medellín → Bogotá → Cartagena
$821
$1,863
$2,683.77
Bogotá → Medellín → Cartagena
$801
$1,908
$2,709.39
Medellín → Cartagena → Bogotá
$752
$1,996
$2,747.64
Bogotá → Cartagena → Medellín
$792
$2,022
$2,813.99
Cartagena → Bogotá → Medellín
$866
$2,022
$2,887.99
Cartagena → Medellín → Bogotá
~$803
$2,041
~$2,844
Medellín-first is still the cheapest combined option — but the margin over Bogotá-first shrinks from $46 (hotels alone) to about $26 (flights and hotels combined), because Bogotá-first's flights ran about $20 cheaper. Add one more layer of nuance: the third-place order, Medellín → Cartagena → Bogotá, actually has the cheapest flights of the entire set ($752) — but its hotel total is high enough that it still finishes behind the top two overall.
Why This Is Easy to Miss
Hotel comparisons are simple to run six times over — same search, six date windows, six totals. Flight comparisons across different entry and exit cities are a different kind of search entirely, and the two totals move independently of each other. A traveler who stops at the hotel comparison walks away thinking the savings are $46 when the real, all-in number is closer to $26 — still worth taking, but not the number the hotel-only search suggested.
The generalizable point: whichever city order looks cheapest on hotels is a hypothesis, not the answer, until flights are priced against that same order and added back in.
How to Run This Comparison for Your Own Trip
Manually, this means pricing hotels for every valid city order, then separately pricing international and domestic flights for the same set of orders, then lining up both totals side by side — six searches on the hotel side and six more (each involving multiple flight legs) on the flight side, for a three-city trip. A fourth city turns six orders into twenty-four.
This is exactly what FortripAI's Optimization Agent is built to run in one pass. Give it your cities, fixed hotels or preferences, dates, and departure city, and it prices every valid order — hotels and flights together — and surfaces the combined total, instead of stopping at whichever half of the comparison is easier to run by hand.
FAQ: Comparing Total Cost Across Multi-City Orders
Does comparing hotel prices alone tell me the cheapest city order for a trip?
Not reliably. In one real Colombia itinerary, the order with the cheapest hotels also had the cheapest combined total — but the advantage was roughly half of what the hotel-only comparison suggested, once flights were added back in.
Why would flights change the ranking that hotels alone suggested?
International flight prices depend heavily on which city you fly into and out of, not just which cities you visit. A city order that's cheaper on hotels can carry a flight premium (or a flight discount) that moves independently of the hotel savings.
Do domestic flights between cities matter as much as the international flight?
Less, usually — domestic legs are typically smaller dollar amounts than the international entry and exit fares, but they still add up across three or four separate short flights and are worth including in the total rather than assumed to be roughly equal across orders.
Is the geographically obvious route ever close to the cheapest option?
Sometimes, yes. In this case, the more intuitive order (flying into the country's main hub first) came in only about $26 more than the mathematically cheapest order — often a reasonable trade for a simpler, more direct routing.
How many city orders do I need to check for a 3 or 4-city trip?
Three cities have 6 possible orders; four cities have 24. Checking all of them by hand across both hotels and flights gets unwieldy fast, which is the main reason most people only ever compare the hotel side.
Planning a multi-city trip with a fixed set of hotels or destinations? Try FortripAI's Optimization Agent — enter your cities, dates, and departure point, and let it price every order's hotels and flights together to find the actual cheapest total.
