Deal found on October 7, 2026
Madison to Havana
$370$48824% off
Round trip
American is flying Madison to Havana for $370 round trip, down from the usual $505 for this route. The same fare just popped up at several other Midwest airports, so it looks like a genuine Havana sale rather than a one-off. Havana's old town architecture and easy day trips to Varadero's beaches make it one of the most walkable, affordable Caribbean trips you can book this fall and winter.
Travel dates
Dates in November
e.g. Nov 1 – Nov 10 · 9 nights
Date options
14 at this price
Lowest we've seen
$332
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