Verdict: choose Bergamo for a relaxed, budget-friendly medieval hill town; stay in Milan for fashion, art and big-city energy. • Bergamo: the Città Alta is a medieval hill town reached by funicular, with Piazza Vecchia and the UNESCO Venetian Walls; the regional train from Milan is about €5.50 each way (≈50 min / 60 km), and the round-trip funicular is about €5, so transport totals roughly €16. • Milan: the Duomo (terrace about €10), Galleria Vittorio Emanuele II, The Last Supper and Sforza Castle; a single transit ticket costs about €2. • Costs: a mid-range meal runs about €15–25 per person in Bergamo vs €20–30 in Milan; hotels start around €50 in Bergamo and €70 in Milan. • Note: Milan Bergamo Airport (Orio al Serio) is actually in Bergamo — about 15 min by bus to Bergamo centre, but roughly 1 hour to central Milan.