In 2006, a tiny pricing error turned into one of the wildest business-class deals ever seen—and a multimillion‑dollar lesson for airlines worldwide.

The $39 Business-Class Ticket That Broke the Budget

Imagine opening your laptop and spotting a business‑class ticket from Toronto to Cyprus for the price of a cheap dinner.

No promo code, no hidden catch - just a checkout page showing around 39 dollars for a route that normally runs close to 3,900 dollars one way. That is exactly what happened in 2006 when Italian carrier Alitalia mispriced its Toronto - Larnaca (Cyprus) business‑class fares. A simple clerical error dropped two zeros from the fare filing, turning an expensive long‑haul premium cabin into the deal of a lifetime.

What went wrong? Here’s the quick breakdown:

Alitalia filed a business‑class fare of roughly 3,900 dollars for Toronto-Cyprus. A mistake in the reservation/pricing system chopped off the last two zeros, displaying the fare as about 39 dollars instead. The error went live online and was picked up by early‑2000s travel forums and deal hunters, who started booking fast. Depending on the source, hundreds to around 2,000 tickets were snapped up before the airline could patch the mistake. Instead of pulling the plug on customers, Alitalia chose to honor almost all of the error fares, effectively giving away premium cabin seats for under 40 dollars.

The bill: about $7.2 million! Honoring those tickets came with a serious price tag.Estimates put the lost revenue from the glitch at around 7 to 7.7 million dollars once all the mispriced tickets were flown.

This hit landed on an airline that was already struggling financially and would later file for bankruptcy protection in 2008, before eventually ceasing operations in 2021. Was the typo the sole reason Alitalia failed? No. The airline was already dealing with deep structural and financial problems. But the $39 fare fiasco has become one of the most famous examples of how a tiny back‑office error can snowball into a multimillion‑dollar headache.

Why this matters for travelers today?

Even though this happened in 2006, twenty years later, in 2026, mistake fares still slip through - and savvy travelers who move quickly can score huge value before the plug gets pulled.

For deal hunters, the lesson is simple: when a premium‑cabin fare looks wildly off, book first, ask questions later, and always wait to make nonrefundable plans until the ticket tickets and the airline confirms it (wait 24 to 48 hours before confirming with the airline so they don't cancel the deal)

How you can pounce on the next glitch and here are a few practical ways to be ready if another “$39 business‑class” moment appears:

1) Stay plugged into real‑time deal alerts by subscribing to 5TownsFlights, the #1 source for mistake fares and flash sales primarily from JFK (as well as other local airports).

2) Be flexible on routes and dates; most error fares are ultra‑specific and vanish fast.

3) Keep a “go bag” of information ready - valid passport, rough travel wish list, and a backup plan in case the airline cancels and refunds the ticket.

Want to be among the first to hear when fares drop to “this has to be a typo” levels? Make sure you’re subscribed with your best email, share this story with a friend who loves flying in style for economy‑level prices, and stay tuned - because the next legendary deal could pop up any day (and Premium members get instant alerts and a free travel concierge!)