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 $440 a person and the most expensive at $552, a difference of $112 for visiting exactly the same places.
Fly them in this order
Dallas → New York → Chicago → Los Angeles → Dallas
About $440 per person in flights, based on fares recently seen on these routes.
One press plans it on January 16, 2027 to January 30, 2027 for 2 travelers.
Plan this trip on real datesEvery order, priced
- Dallas → New York → Chicago → Los Angeles → Dallas$440cheapest order
- Dallas → Los Angeles → Chicago → New York → Dallas$452$12 more per person
- Dallas → New York → Los Angeles → Chicago → Dallas$472$32 more per person
- Dallas → Chicago → New York → Los Angeles → Dallas$473$33 more per person
- Dallas → Chicago → Los Angeles → New York → Dallas$485$45 more per person
- Dallas → Los Angeles → New York → Chicago → Dallas$552$112 more per person
Why New York first
- Dallas to New York$101
- New York to Chicago$116
- Chicago to Los Angeles$124
- Los Angeles to Dallas$99
- Out of Dallas, New York is the cheapest first stop at about $101. Los Angeles would be $152.
- Going home, Los Angeles is the cheapest city to leave from at about $99, against $140 from Chicago.
- Los Angeles to Chicago is about $87, but the other way round is $124. Same two cities, $37 apart on direction alone.
- The dearest order pays $152 for Dallas to Los Angeles, a flight the cheapest order never takes.
Between the cities
- New York to Chicago: about 1,140 km (710 miles) as the crow flies. No train or bus we would suggest instead of flying.
- Chicago to Los Angeles: about 2,800 km (1740 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 $112 a person on this trip, 25% of what the cheapest way round costs. Among the 107 trips we price in full, it sits 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 13, 2026, from fares departing November 13, 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
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 Chicago, Los Angeles and New York from DallasOpen the form instead and pick your own datesWhat a plan adds, and the limits
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.
Without an account, 2 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.