Find out what a flight from Chicago Midway to Havana might cost

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

Select your dates to check current offers.

Try shifting your departure forward or backward by a day to find better options. If you’re looking for a good deal, consider flying outside peak hours as well.

Exploring all airports near Chicago and Havana

Checking all the airports available in the area can give you more departure and arrival options for your trip.

• Airports in Chicago: 3 different airports operate in Chicago - Midway, O'Hare, Rockford.
• Airports in Havana: Havana is the only option available right now.

Looking at expected traffic to the airport can help avoid surprises on departure day. On busy routes, flying from a quieter airport might also save you money.

Choose the right flight for your trip from Chicago Midway 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.