The cheapest order to fly New York, Miami and Havana from Madrid
There are 6 ways to fly these cities. They do not cost the same. The cheapest works out at about €1,097 a person and the most expensive at €1,269, a difference of €172 for visiting exactly the same places.
Fly them in this order
Madrid → New York → Havana → Miami → Madrid
About €1,097 per person in flights, based on fares recently seen on these routes.
Shown in euros, converted from US dollars at today’s rate, so every amount is approximate. In dollars the cheapest order is about $1,221. You pay in the airline’s currency.
Every order, priced
- Madrid → New York → Havana → Miami → Madrid€1,097cheapest order
- Madrid → Miami → Havana → New York → Madrid€1,164€66 more per person
- Madrid → Havana → New York → Miami → Madrid€1,183€86 more per person
- Madrid → Havana → Miami → New York → Madrid€1,188€91 more per person
- Madrid → New York → Miami → Havana → Madrid€1,212€115 more per person
- Madrid → Miami → New York → Havana → Madrid€1,269€172 more per person
Why New York first
- Madrid to New York€250
- New York to Havana€294
- Havana to Miami€264
- Miami to Madrid€289
- Out of Madrid, New York is the cheapest first stop at about €250. Havana would be €547.
- Going home, Miami is the cheapest city to leave from at about €289, against €584 from Havana.
- Havana to New York is about €262, but the other way round is €294. Same two cities, €31 apart on direction alone.
- The dearest order pays €584 for Havana to Madrid, a flight the cheapest order never takes.
Between the cities
- New York to Havana: about 2,110 km (1310 miles) as the crow flies. No train or bus we would suggest instead of flying.
- Havana to Miami: about 370 km (230 miles) as the crow flies. No train or bus we would suggest instead of flying.
Entry rules for the United States and Cuba depend on your passport. Check them with the IATA Travel Centre before you book.
How much the order matters here
Getting the order right is worth €172 a person on this trip, 16% of what the cheapest way round costs. Of the 72 trips we price in full, that is number 55 for how much the order matters, one of the smaller gaps: on this trip your dates are likely to matter more than the order.
What these numbers are
Cached one-way fares, 12 of 12 legs priced from real observations, put together on October 29, 2026, from fares departing October 30, 2026 onwards. Right for comparing one order with another, not a quote for your dates.
A plan prices your own dates and weighs hours as well as fares, so it can pick a different order from this page.
Put dates on it
Same cities on real dates, plus what one search cannot show: layovers long enough to count as a free city, two tickets that beat one, and cheaper days either side. No account and no card.
One press starts it on January 2, 2027 to January 16, 2027, 14 days, for 2 travelers. Our dates, not yours, and about two minutes.
Plan New York, Miami and Havana from Madrid nowOpen the form instead and pick your own datesSigned out, 3 plans a day per address, priced from cached fares and the free sources, so some legs may be estimates and the plan says which. Signed in, legs are checked live, with 2 free trips you can change afterwards.