The cheapest order to fly Mexico City, Cancun and Havana from New York
There are 6 ways to fly these cities. They do not cost the same. The cheapest works out at about $807 a person and the most expensive at $956, a difference of $149 for visiting exactly the same places.
Fly them in this order
New York → Cancun → Havana → Mexico City → New York
About $807 per person in flights, based on fares recently seen on these routes.
Every order, priced
- New York → Cancun → Havana → Mexico City → New York$807cheapest order
- New York → Mexico City → Cancun → Havana → New York$817$10 more per person
- New York → Cancun → Mexico City → Havana → New York$824$17 more per person
- New York → Havana → Mexico City → Cancun → New York$941$134 more per person
- New York → Havana → Cancun → Mexico City → New York$955$148 more per person
- New York → Mexico City → Havana → Cancun → New York$956$149 more per person
Why Cancun first
- New York to Cancun$158
- Cancun to Havana$225
- Havana to Mexico City$257
- Mexico City to New York$167
- Out of New York, Cancun is the cheapest first stop at about $158. Havana would be $462.
- Going home, the cheapest flight leaves from Cancun at about $166, but the cheapest order ends in Mexico City at $167 because the rest of the route is cheaper that way.
- Cancun to Havana is about $225, but the other way round is $276. Same two cities, $51 apart on direction alone.
- The dearest order pays $297 for Mexico City to Havana, a flight the cheapest order never takes.
Between the cities
- Cancun to Havana: about 510 km (320 miles) as the crow flies. No train or bus we would suggest instead of flying.
- Havana to Mexico City: about 1,780 km (1110 miles) as the crow flies. No train or bus we would suggest instead of flying.
Entry rules on a US passport
- US passport: no visa for Mexico; keep the FMM/arrival record if issued. Official source
- US passport: travel to Cuba is restricted to licensed categories under US law; a tourist card is also required. Official source
Rules change; check the official source for your passport and dates before you book.
How much the order matters here
Getting the order right is worth $149 a person on this trip, 18% of what the cheapest way round costs. Of the 107 trips we price in full, that is number 68 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 14, 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 Mexico City, Cancun and Havana from New York 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.