Cheap flights from Chicago to Havana

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What’s the cost of a flight from Chicago 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.

Which departure and arrival airports are available?

Between Chicago and Havana, flight options may depend on the combination of airports available.

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

Sometimes flying into a nearby city can be more cost-effective. When a city has multiple airports, it’s worth comparing different flight combinations.

Flights from Chicago to Havana

Plan your journey from Chicago to Havana with ease

Use Jetcost to tailor your search — direct or connecting flights, round-trip or one-way, filtered by airline, price, travel time, or agency.

Other popular destinations

Exploring options in Cuba? These cities are trending: Camaguey, Havana, Holguin, Santa Clara, Santiago de Cuba.

Flight availability can change quickly — refresh the results if you’ve been away from the page for a while.
Frequently Asked Questions

Frequently asked questions about flights from Chicago to Havana.

How much does an airline ticket from Chicago to Havana cost?

Flight prices can vary a lot depending on the period and destination. At the moment, this information is not available for flights from Chicago to Havana.

How far is Chicago from Havana?

Chicago is about 2152 km from Havana.

What are the airports in Havana?

Havana has one airport: Havana.

What are the airports in Chicago?

Chicago has 3 airports: Midway, O'Hare, Rockford.

What are the most popular cities in Cuba?

The most popular cities in Cuba according to our users' searches are: Camaguey, Havana, Holguin, Santa Clara, Santiago de Cuba.

When should I book a flight from Chicago to Havana?

This information is not available at the moment.

What is the cheapest month to fly from Chicago to Havana?

This information is not available at the moment.

What is the most expensive month to fly from Chicago to Havana?

This information is not available at the moment.

What is the best day of the week to fly from Chicago to Havana?

This information is not available at the moment.