The cheapest order to fly Chicago, Los Angeles and New York from Dallas
There are 6 ways to fly these cities. They do not cost the same. The cheapest works out at about $427 a person and the most expensive at $537, a difference of $110 for visiting exactly the same places.
Fly them in this order
Dallas → Chicago → Los Angeles → New York → Dallas
About $427 per person in flights, based on fares recently seen on these routes.
Every order, priced
- Dallas → Chicago → Los Angeles → New York → Dallas$427cheapest order
- Dallas → New York → Chicago → Los Angeles → Dallas$429$2 more per person
- Dallas → Los Angeles → Chicago → New York → Dallas$446$19 more per person
- Dallas → New York → Los Angeles → Chicago → Dallas$457$30 more per person
- Dallas → Chicago → New York → Los Angeles → Dallas$524$97 more per person
- Dallas → Los Angeles → New York → Chicago → Dallas$537$110 more per person
Why end in New York
- Dallas to Chicago$112
- Chicago to Los Angeles$100
- Los Angeles to New York$144
- New York to Dallas$71
- Out of Dallas, the cheapest first flight goes to New York at about $75, but the cheapest order starts in Chicago at $112 because the rest of the route is cheaper that way.
- Going home, New York is the cheapest city to leave from at about $71, against $148 from Los Angeles.
- New York to Chicago is about $106, but the other way round is $122. Same two cities, $16 apart on direction alone.
Between the cities
- Chicago to Los Angeles: about 2,800 km (1740 miles) as the crow flies. No train or bus we would suggest instead of flying.
- Los Angeles to New York: about 3,940 km (2450 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 $110 a person on this trip, 26% of what the cheapest way round costs. Of the 107 trips we price in full, that is number 41 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 10, 2026, from fares departing November 9, 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 Chicago, Los Angeles and New York from Dallas 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.