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The cheapest order to fly Tallinn, Riga and Vilnius 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 $945 a person and the most expensive at $1,007, a difference of $62 for visiting exactly the same places.

Fly them in this order

Chicago → Riga → Tallinn → Vilnius → Chicago

About $945 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 → Riga → Tallinn → Vilnius → Chicago$945
    cheapest order
  2. Chicago → Riga → Vilnius → Tallinn → Chicago$1,007
    $62 more per person

Why end in Vilnius

  1. Chicago to Riga$397
  2. Riga to Tallinn$54
  3. Tallinn to Vilnius$25
  4. Vilnius to Chicago$469
  • Going home, Vilnius is the cheapest city to leave from at about $469, against $539 from Tallinn.
  • The dearest order pays $539 for Tallinn to Chicago, a flight the cheapest order never takes.
  • Vilnius to Chicago is 50% of what the cheapest order spends on flights, so it is the leg to watch.

Between the cities

  • Riga to Tallinn: about 280 km (170 miles) as the crow flies. Also by ground: Lux Express / FlixBus, about 4h 30m, usually $15 to $30.
  • Tallinn to Vilnius: about 530 km (330 miles) as the crow flies. Also by ground: Lux Express / FlixBus, about 9h, usually $30 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 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.

What these numbers are

Cached one-way fares, 9 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.

Plan Tallinn, Riga and Vilnius from Chicago nowOpen the form instead and pick your own dates

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.