What’s the cost of a flight from Chicago O'Hare 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.

Best airport options between Chicago and Havana

If you're open to flying into or out of more than one airport, you’ll have more routes to compare.

• Airports in Chicago: Chicago is served by 3 airports - Midway, O'Hare, Rockford.
• Airports in Havana: Havana is the sole airport currently available.

Some airports offer extras like lounges, fast track, or self check-in — good to keep in mind. Comparing airports by services offered helps you balance cost and comfort.

Smart ways to search flights from Chicago O'Hare to Havana

Use Jetcost to view tailored results based on what you care about — time, duration, number of stops, or even your preferred booking agency. Results include the best airlines and travel agencies.

Other popular destinations

Flying to Cuba? Other travelers also searched: Camaguey, Havana, Holguin, Santa Clara, Santiago de Cuba.

Prefer non-stop flights? Just activate the filter to skip unnecessary layovers. If your dates are flexible, you can also explore different departure and return combinations to find the best fit.