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The cheapest order to fly Berlin, Hamburg and Munich from Chicago

There are 6 ways to fly these cities. They do not cost the same. The cheapest works out at about $1,109 a person and the most expensive at $1,359, a difference of $250 for visiting exactly the same places.

Fly them in this order

Chicago → Berlin → Munich → Hamburg → Chicago

About $1,109 per person in flights, based on fares recently seen on these routes.

Every order, priced

  1. Chicago → Berlin → Munich → Hamburg → Chicago$1,109
    cheapest order
  2. Chicago → Munich → Berlin → Hamburg → Chicago$1,114
    $5 more per person
  3. Chicago → Munich → Hamburg → Berlin → Chicago$1,171
    $62 more per person
  4. Chicago → Hamburg → Munich → Berlin → Chicago$1,243
    $134 more per person
  5. Chicago → Berlin → Hamburg → Munich → Chicago$1,244
    $135 more per person
  6. Chicago → Hamburg → Berlin → Munich → Chicago$1,359
    $250 more per person

Why end in Hamburg

  1. Chicago to Berlin$450
  2. Berlin to Munich$101
  3. Munich to Hamburg$95
  4. Hamburg to Chicago$463
  • Out of Chicago, the cheapest first flight goes to Munich at about $404, but the cheapest order starts in Berlin at $450 because the rest of the route is cheaper that way.
  • Going home, Hamburg is the cheapest city to leave from at about $463, against $583 from Munich.
  • Hamburg to Munich is about $75, but the other way round is $95. Same two cities, $20 apart on direction alone.
  • The dearest order pays $583 for Munich to Chicago, a flight the cheapest order never takes.
  • Hamburg to Chicago is 42% of what the cheapest order spends on flights, so it is the leg to watch.

Between the cities

  • Berlin to Munich: about 500 km (310 miles) as the crow flies. Also by ground: ICE, about 4h, usually $40 to $120.
  • Munich to Hamburg: about 610 km (380 miles) as the crow flies. Also by ground: ICE, about 6h, usually $30 to $150.

Entry rules on a US passport

  • US passport: visa-free in the Schengen area for 90 days in any 180. The Entry/Exit System registers biometrics at the border, and the ETIAS pre-travel authorisation may now be required; check the official site. Official source

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

How much the order matters here

Getting the order right is worth $250 a person on this trip, 23% of what the cheapest way round costs. Of the 73 trips we price in full, that is number 37 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 October 29, 2026, from fares departing October 30, 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 2, 2027 to January 16, 2027, 14 days, for 2 travelers. Our dates, not yours, and about two minutes.

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Signed out, 3 plans 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.