The cheapest order to fly Berlin, Prague and Vienna from Chicago
There are 6 ways to fly these cities, and 4 of them can be priced from fares we have seen. Of those, 2 tie for the cheapest. The cheapest works out at about $977 a person and the most expensive at $1,336, a difference of $359 for visiting exactly the same places.
Fly them in this order
Chicago → Berlin → Prague → Vienna → Chicago
About $977 per person in flights, based on fares recently seen on these routes, and the cheapest of the 4 ways round we could price.
The 4 we can price
- Chicago → Berlin → Prague → Vienna → Chicago$977cheapest order
- Chicago → Berlin → Vienna → Prague → Chicago$977same price
- Chicago → Prague → Berlin → Vienna → Chicago$1,006$29 more per person
- Chicago → Vienna → Berlin → Prague → Chicago$1,336$359 more per person
Why Berlin first
- Chicago to Berlin$341
- Berlin to Prague$90
- Prague to Vienna$61
- Vienna to Chicago$485
- Out of Chicago, Berlin is the cheapest first stop at about $341. Vienna would be $688.
- Going home, Vienna is the cheapest city to leave from at about $485, against $504 from Prague.
- The dearest order pays $688 for Chicago to Vienna, a flight the cheapest order never takes.
- Vienna to Chicago is 50% of what the cheapest order spends on flights, so it is the leg to watch.
Between the cities
- Berlin to Prague: about 280 km (170 miles) as the crow flies. Also by ground: EC, about 4h 20m, usually $25 to $60.
- Prague to Vienna: about 250 km (160 miles) as the crow flies. Also by ground: Railjet / RegioJet, about 4h, usually $20 to $50.
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 authorization may now be required; check the official site. Official source
Rules change; check the official source for your passport and dates before you book.
The same cities from other airports
The cheapest order depends on where you start. From Chicago it starts in Berlin.
- 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, 11 of 12 legs priced from real observations, put together on November 12, 2026, from fares departing November 18, 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 16, 2027 to January 30, 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 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.