The cheapest order to fly Mexico City, Cancun and Guadalajara from San Francisco
There are 6 ways to fly these cities, and 4 of them can be priced from fares we have seen. They do not cost the same. The cheapest works out at about $574 a person and the most expensive at $662, a difference of $88 for visiting exactly the same places.
Fly them in this order
San Francisco → Mexico City → Cancun → Guadalajara → San Francisco
About $574 per person in flights, based on fares recently seen on these routes, and the cheapest of the 4 ways round we could price.
The 4 we can price
- San Francisco → Mexico City → Cancun → Guadalajara → San Francisco$574cheapest order
- San Francisco → Cancun → Mexico City → Guadalajara → San Francisco$590$16 more per person
- San Francisco → Mexico City → Guadalajara → Cancun → San Francisco$622$48 more per person
- San Francisco → Cancun → Guadalajara → Mexico City → San Francisco$662$88 more per person
Why Mexico City first
- San Francisco to Mexico City$203
- Mexico City to Cancun$56
- Cancun to Guadalajara$93
- Guadalajara to San Francisco$222
- Out of San Francisco, Mexico City is the cheapest first stop at about $203. Cancun would be $279.
- Going home, Guadalajara is the cheapest city to leave from at about $222, against $286 from Cancun.
- The dearest order pays $279 for San Francisco to Cancun, a flight the cheapest order never takes.
Between the cities
- Mexico City to Cancun: about 1,290 km (800 miles) as the crow flies. No train or bus we would suggest instead of flying.
- Cancun to Guadalajara: about 1,710 km (1060 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
Rules change; check the official source for your passport and dates before you book.
What these numbers are
Cached one-way fares, 11 of 12 legs priced from real observations, put together on October 29, 2026, from fares departing November 1, 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 Mexico City, Cancun and Guadalajara from San Francisco 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.