The cheapest order to fly Los Angeles, Miami and San Francisco from Chicago
There are 6 ways to fly these cities. They do not cost the same. The cheapest works out at about $327 a person and the most expensive at $548, a difference of $221 for visiting exactly the same places.
Fly them in this order
Chicago → Los Angeles → San Francisco → Miami → Chicago
About $327 per person in flights, based on fares recently seen on these routes.
Every order, priced
- Chicago → Los Angeles → San Francisco → Miami → Chicago$327cheapest order
- Chicago → Miami → San Francisco → Los Angeles → Chicago$340$13 more per person
- Chicago → San Francisco → Los Angeles → Miami → Chicago$361$34 more per person
- Chicago → Miami → Los Angeles → San Francisco → Chicago$392$65 more per person
- Chicago → San Francisco → Miami → Los Angeles → Chicago$472$145 more per person
- Chicago → Los Angeles → Miami → San Francisco → Chicago$548$221 more per person
Why end in Miami
- Chicago to Los Angeles$100
- Los Angeles to San Francisco$20
- San Francisco to Miami$123
- Miami to Chicago$84
- Out of Chicago, the cheapest first flight goes to Miami at about $74, but the cheapest order starts in Los Angeles at $100 because the rest of the route is cheaper that way.
- Going home, Miami is the cheapest city to leave from at about $84, against $192 from San Francisco.
- San Francisco to Miami is about $123, but the other way round is $141. Same two cities, $18 apart on direction alone.
- The dearest order pays $192 for San Francisco to Chicago, a flight the cheapest order never takes.
Between the cities
- Los Angeles to San Francisco: about 560 km (350 miles) as the crow flies. Also by ground: FlixBus / Greyhound, about 7h 30m, usually $25 to $70.
- San Francisco to Miami: about 4,170 km (2590 miles) as the crow flies. No train or bus we would suggest instead of flying.
How much the order matters here
Getting the order right is worth $221 a person on this trip, 68% of what the cheapest way round costs. Of the 107 trips we price in full, that is number 6 for how much the order matters, one of the trips where it matters most: flying these cities in the wrong order is an expensive mistake.
What these numbers are
Cached one-way fares, 12 of 12 legs priced from real observations, put together on November 10, 2026, from fares departing November 10, 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 9, 2027 to January 23, 2027, 14 days, for 2 travelers. Our dates, not yours, and about two minutes.
Plan Los Angeles, Miami and San Francisco from Chicago 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, legs are checked live, with 2 free trips you can change afterwards.