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

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

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.

What are the airport options between Chicago and Havana?

If both departure and destination cities offer multiple airports, comparing them can help you save time and money.

• Airports in Chicago: Chicago has 3 airports - Midway, O'Hare, Rockford.
• Airports in Havana: Havana has one airport operating, Havana.

Some airports have different terminals for low-cost and traditional airlines — knowing in advance can save time. You can filter results to see only the airports that suit you.

Find flights from Chicago Midway to Havana that suit your schedule

Use Jetcost to sort and filter results based on your preferred flight time, number of stops, price range, or airline. View deals from the best airlines and travel agencies.

Other popular destinations

Interested in Cuba? These cities are also in demand: Camaguey, Havana, Holguin, Santa Clara, Santiago de Cuba.

Connecting flights can be cheaper but often mean longer layovers. You can easily select either direct or connecting flights with a single click using the filters.