How much is a ticket from Chicago to Havana?

Depending on when you travel and how far in advance you book, fares between Chicago and Havana can differ a lot.

Choose a date to explore the best fares now.

If you’re flexible with timing, consider overnight flights — they often cost less and are less crowded. Exploring multiple date and time combinations can help you find the cheapest solution.

Planning flights between Chicago and Havana? Don’t forget the airport options

Especially when flying to medium or large cities, it's worth checking all possible airport combinations before booking.

• Airports in Chicago: 3 airports are listed in Chicago - Midway, O'Hare, Rockford.
• Airports in Havana: Only Havana is currently available.

Check for differences in transport costs to and from each airport — they affect your total spend. Choosing the right airport can make a real difference in price and timing.

Choose the right flight for your trip from Chicago to Havana

Jetcost helps you tailor your flight search based on what matters to you — flight length, budget, airline, or agency. Whether you prefer round-trip or one-way, direct or with stopovers, you’ll see options from the best airlines and travel agencies.

Other popular destinations

Flying to Cuba? Many users also explore: Camaguey, Havana, Holguin, Santa Clara, Santiago de Cuba.

Looking for a specific airline? Select it directly in the filters to speed up your search. The search filters help you see only the options that match your needs.