How much is a ticket from Chicago O'Hare to Havana?

Flight prices from Chicago to Havana change depending on demand and time of booking.

Select your dates to check current offers.

Flying at off-peak hours — such as early morning or late evening — can help you save. Also, the best deals tend to appear in the weeks leading up to departure.

Which airports serve Chicago and Havana?

When planning a trip of about 1350 mi, it's a good idea to check flights from surrounding airports too.

• Airports in Chicago: Chicago is connected to 3 airports - Midway, O'Hare, Rockford.
• Airports in Havana: The only active airport in Havana is Havana.

The closest airport isn’t always the cheapest — it’s worth checking the alternatives too. In some cities, smaller airports offer lower fares than the main ones.

Refine your flight search from Chicago O'Hare to Havana

With Jetcost, it’s easy to narrow down results to find flights that match your schedule and preferences. You can filter by airline, price, trip type, and more — including offers from Expedia, eDreams, and top carriers.

Other popular destinations

Also looking at Cuba? These cities are trending: Camaguey, Havana, Holguin, Santa Clara, Santiago de Cuba.

Online agencies can show different offers for the same flight — it’s worth comparing. Filters let you narrow things down further, like selecting a specific time slot to find flights that suit you best.