What’s the cost of a flight from Havana to Chicago Midway?

Prices vary based on date, airline, and availability. Compare several options if you're flying between Havana and Chicago.

Choose a date to explore the best fares now.

If possible, avoid holiday periods: ticket prices tend to rise quickly and availability drops, especially on busy routes. Morning and evening flights are often in high demand too — book early to get a good fare.

Which airports are most convenient between Havana and Chicago?

Whether it’s cost or connection time, the right airport combination can make a difference.

• Airports in Havana: Only Havana is currently active.
• Airports in Chicago: In Chicago you can fly to/from 3 airports - Midway, O'Hare, Rockford.

In some cases, flying into a secondary airport can also reduce transfer costs. Connections from multiple airports give you more flight options and airlines.

Compare flights from Havana to Chicago Midway with advanced filters

Find your ideal flight using Jetcost. Select whether you want nonstop or connecting flights, round-trip or one-way, and filter by airline, price, or booking site.

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If you have a preferred time to leave or arrive, filters can help you show only the matching flights. You can also filter by your favorite airline and see only those deals.