Looking for the price of a flight from Havana to Chicago Midway?

There’s no fixed price — fares between Havana and Chicago can vary a lot by day or time.

Select your dates to check current offers.

It’s often useful to check whether nearby airports offer better fares. Flying during less crowded periods also increases your chances of finding good deals.

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.

Find the best flight from Havana to Chicago Midway

With Jetcost, you can filter results by flight time, airline, price range, and layovers. Choose direct or connecting flights, round-trip or one-way, and compare offers from Delta, American, United, and more.

Other popular destinations

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Use filters to exclude options that don’t match your budget or travel preferences and personalize your search for Havana – Chicago Midway flights.