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 €1,112 a person and the most expensive at €1,344, a difference of €232 for visiting exactly the same places.
Fly them in this order
Madrid → Havana → Miami → New York → Madrid
About €1,112 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 $1,232. You pay in the airline’s currency.
Every order, priced
- Madrid → Havana → Miami → New York → Madrid€1,112cheapest order
- Madrid → Miami → Havana → New York → Madrid€1,115€3 more per person
- Madrid → New York → Miami → Havana → Madrid€1,165€53 more per person
- Madrid → Havana → New York → Miami → Madrid€1,211€99 more per person
- Madrid → New York → Havana → Miami → Madrid€1,235€124 more per person
- Madrid → Miami → New York → Havana → Madrid€1,344€232 more per person
Why end in New York
- Madrid to Havana€538
- Havana to Miami€258
- Miami to New York€85
- New York to Madrid€231
- Out of Madrid, the cheapest first flight goes to New York at about €251, but the cheapest order starts in Havana at €538 because the rest of the route is cheaper that way.
- Going home, New York is the cheapest city to leave from at about €231, against €542 from Havana.
- Havana to New York is about €288, but the other way round is €417. Same two cities, €129 apart on direction alone.
- Madrid to Havana is 48% of what the cheapest order spends on flights, so it is the leg to watch.
Between the cities
- Havana to Miami: about 370 km (230 miles) as the crow flies. No train or bus we would suggest instead of flying.
- Miami to New York: about 1,760 km (1090 miles) as the crow flies. No train or bus we would suggest instead of flying.
Entry rules for Cuba and the United States 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 €232 a person on this trip, 21% of what the cheapest way round costs. Of the 107 trips we price in full, that is number 57 for how much the order matters, about the middle: worth getting right, and worth checking against your own dates.
What these numbers are
Cached one-way fares, 12 of 12 legs priced from real observations, put together on November 12, 2026, from fares departing November 13, 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 16, 2027 to January 30, 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 trips 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, your first trip also searches Google Flights live, and you can change your trips afterwards.