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 $333 a person and the most expensive at $510, a difference of $177 for visiting exactly the same places.
Fly them in this order
Chicago → Miami → San Francisco → Los Angeles → Chicago
About $333 per person in flights, based on fares recently seen on these routes.
Every order, priced
- Chicago → Miami → San Francisco → Los Angeles → Chicago$333cheapest order
- Chicago → Miami → Los Angeles → San Francisco → Chicago$335$2 more per person
- Chicago → San Francisco → Los Angeles → Miami → Chicago$343$10 more per person
- Chicago → Los Angeles → San Francisco → Miami → Chicago$354$21 more per person
- Chicago → San Francisco → Miami → Los Angeles → Chicago$481$148 more per person
- Chicago → Los Angeles → Miami → San Francisco → Chicago$510$177 more per person
Why Miami first
- Chicago to Miami$80
- Miami to San Francisco$143
- San Francisco to Los Angeles$21
- Los Angeles to Chicago$89
- Out of Chicago, Miami is the cheapest first stop at about $80. San Francisco would be $140.
- Going home, the cheapest flight leaves from Miami at about $66, but the cheapest order ends in Los Angeles at $89 because the rest of the route is cheaper that way.
- Miami to San Francisco is 43% of what the cheapest order spends on flights, so it is the leg to watch.
Between the cities
- Miami to San Francisco: about 4,170 km (2590 miles) as the crow flies. No train or bus we would suggest instead of flying.
- San Francisco to Los Angeles: about 560 km (350 miles) as the crow flies. Also by ground: FlixBus / Greyhound, about 7h 30m, usually $25 to $70.
How much the order matters here
Getting the order right is worth $177 a person on this trip, 53% of what the cheapest way round costs. Of the 107 trips we price in full, that is number 10 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 12, 2026, from fares departing November 16, 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 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, your first trip also searches Google Flights live, and you can change your trips afterwards.