The cheapest order to fly Berlin, Prague and Vienna from Chicago
There are 6 ways to fly these cities. They do not cost the same. The cheapest works out at about $1,059 a person and the most expensive at $1,221, a difference of $162 for visiting exactly the same places.
Fly them in this order
Chicago → Prague → Vienna → Berlin → Chicago
About $1,059 per person in flights, based on fares recently seen on these routes.
Every order, priced
- Chicago → Prague → Vienna → Berlin → Chicago$1,059cheapest order
- Chicago → Prague → Berlin → Vienna → Chicago$1,067$8 more per person
- Chicago → Vienna → Prague → Berlin → Chicago$1,073$14 more per person
- Chicago → Berlin → Prague → Vienna → Chicago$1,154$95 more per person
- Chicago → Vienna → Berlin → Prague → Chicago$1,200$141 more per person
- Chicago → Berlin → Vienna → Prague → Chicago$1,221$162 more per person
The cheapest order, leg by leg
- Chicago to Prague$395
- Prague to Vienna$73
- Vienna to Berlin$64
- Berlin to Chicago$527
- Out of Chicago, the cheapest first flight goes to Vienna at about $391, but the cheapest order starts in Prague at $395 because the rest of the route is cheaper that way.
- Going home, the cheapest flight leaves from Vienna at about $524, but the cheapest order ends in Berlin at $527 because the rest of the route is cheaper that way.
- Prague to Berlin is about $85, but the other way round is $107. Same two cities, $22 apart on direction alone.
- The dearest order pays $638 for Prague to Chicago, a flight the cheapest order never takes.
- Berlin to Chicago is 50% of what the cheapest order spends on flights, so it is the leg to watch.
Between the cities
- Prague to Vienna: about 250 km (160 miles) as the crow flies. Also by ground: Railjet / RegioJet, about 4h, usually $20 to $50.
- Vienna to Berlin: about 520 km (320 miles) as the crow flies. Also by ground: Railjet (via Prague), about 8h 30m, usually $40 to $130.
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 $162 a person on this trip, 15% of what the cheapest way round costs. Of the 72 trips we price in full, that is number 56 for how much the order matters, one of the smaller gaps: on this trip your dates are likely to matter more than the order.
The same cities from other airports
The cheapest order depends on where you start. From Chicago it starts in Prague.
- From New Yorkstart in Prague, about $737 a person, $156 less than the dearest order
- From Torontostart in Prague, about $923 a person, $218 less than the dearest order
- From Bostonstart in Prague, about $998 a person, $147 less than the dearest order
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.
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.
Plan Berlin, Prague and Vienna from Chicago nowOpen the form instead and pick your own datesSigned 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.