Route Price Intelligence
Cheap Flights From Madison to Havana
Live pricing benchmarks, monthly patterns, and historical lows for this route.
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.
✓ 14 date combinations found at this price
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Best Time to Fly from Madison to Havana
The cheapest time to fly from Madison to Havana is typically September, when fares average around $487. The most expensive month tends to be July at around $576. For the best deals, consider flying in September, October, January.
Typical Price by Travel Month
Median round-trip fare for each month, with the typical price range, from our ongoing tracking of this route