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The cheapest order to fly Bangkok, Phuket and Chiang Mai from Chicago

There are 6 ways to fly these cities, and 2 of them can be priced from fares we have seen. They do not cost the same. The cheapest works out at about $1,360 a person and the most expensive at $1,375, a difference of $15 for visiting exactly the same places.

Fly them in this order

Chicago → Phuket → Chiang Mai → Bangkok → Chicago

About $1,360 per person in flights, based on fares recently seen on these routes, and the cheapest of the 2 ways round we could price.

The 2 we can price

  1. Chicago → Phuket → Chiang Mai → Bangkok → Chicago$1,360
    cheapest order
  2. Chicago → Bangkok → Chiang Mai → Phuket → Chicago$1,375
    $15 more per person

Why end in Bangkok

  1. Chicago to Phuket$651
  2. Phuket to Chiang Mai$75
  3. Chiang Mai to Bangkok$38
  4. Bangkok to Chicago$596
  • Out of Chicago, the cheapest first flight goes to Bangkok at about $580, but the cheapest order starts in Phuket at $651 because the rest of the route is cheaper that way.
  • Going home, Bangkok is the cheapest city to leave from at about $596, against $675 from Phuket.
  • The dearest order pays $675 for Phuket to Chicago, a flight the cheapest order never takes.
  • Chicago to Phuket is 48% of what the cheapest order spends on flights, so it is the leg to watch.

Between the cities

  • Phuket to Chiang Mai: about 1,210 km (750 miles) as the crow flies. No train or bus we would suggest instead of flying.
  • Chiang Mai to Bangkok: about 580 km (360 miles) as the crow flies. Also by ground: SRT sleeper train, about 12h overnight, usually $25 to $55. Or Nakhonchai Air (overnight), about 10h, usually $15 to $30.

Entry rules on a US passport

  • US passport: visa-free in Thailand for short tourist stays (currently 60 days); check the digital arrival card requirement. Official source

Rules change; check the official source for your passport and dates before you book.

What these numbers are

Cached one-way fares, 10 of 12 legs priced from real observations, put together on November 12, 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.

Other trips priced this way

From Chicago

Trips through the same cities

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 Bangkok, Phuket and Chiang Mai from Chicago nowOpen the form instead and pick your own dates

Signed 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.