Start with the 07:30 FlixBus bus from Frankfurt to Karlsruhe central, about 1h 23m. Transfer in Karlsruhe central, then take the 09:15 FlixBus bus on to Darmstadt central (1h 12m). Transfer in Frankfurt, then take the 20:10 Condor flight on to Milan (1h 10m). You arrive in Milan around 21:20. In total it's roughly EUR 118 over 12h 45m, 2 transfers.
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Opens Omio — enter your date to compare trains and buses for this route; the price is finalised at checkout.
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Fly into Frankfurt, then continue to Milan by bus (1h 23m) — routing via Frankfurt keeps the trip simple. Bus (FlixBus, 1h 23min) + Bus (FlixBus, 1h 12min) via Karlsruhe central + Flight (Condor, 1h 10min) via Frankfurt.