Cheap Flights from Chicago (ORD) to Havana (HAV)

Popular airlines from Chicago O'Hare Intl. Airport (ORD) to Havana (HAV-Jose Marti Intl.)

Find available prices by choosing your travel dates.
Flights from Chicago (ORD) to Havana (HAV)
Origin airport
O'Hare Intl.
Destination airport
Jose Marti Intl.
Distance
1349 mi

Chicago to Havana Flights

The cheapest times to fly from Chicago to Havana

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Havana are during the month of . You can find some of the cheapest flights from Chicago to Havana with Expedia's search tool and vast selection of airlines.

The best time to book a flight from Chicago to Havana

Sunday is one of the best days to book for cheap flights from Chicago to Havana: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

How to find cheap round-trip tickets from Chicago to Havana

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Havana in 2025. You can also book with separate airlines for your outbound and return journeys, from one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Havana flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

You could also save big by booking one of Expedia's vacation packages. Bundling together your Chicago to Havana airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

*Terms apply.

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

Frequently asked questions

How much does a flight from O'Hare Intl. Airport (ORD) to Havana (HAV-Jose Marti Intl.) cost?
Discover the latest flight deals from ORD to HAV by entering your preferred travel dates and searching on Expedia. Easily compare prices by departure date if you have flexibility with your schedule and use handy filters to explore prices for your preferred journey. As a member of One Key™, our free loyalty program, you can use Price Tracking to watch fares and receive notifications if prices go up or down.
What is the cheapest month to fly from ORD to HAV?
The cheapest flights from ORD to HAV are usually during off-peak season, when demand is lower. To save money, avoid flying during public holidays, school breaks and major local events.
What is the cheapest airline that flies from ORD to HAV?
Use the filter tool on Expedia to compare airlines and find the cheapest carrier that’ll take you from ORD to HAV. Sort your results by “Price (lowest to highest)” to snap up a great deal.
How many flights per day from O'Hare Intl. Airport (ORD) to Havana (HAV-Jose Marti Intl.)?
Nonstop flights from O’Hare Intl. Airport (ORD) to Havana (HAV-Jose Marti Intl.) aren’t available daily, so you’ll have to take a flight with a layover. Explore your options with Expedia’s filter tool. Enter your travel details and click on either “1 Stop” or “2+ Stops.”
What day of the week has the most flights from ORD to HAV?
Usually you’ll find the most flight options available on a Friday. Tuesdays tend to be the quietest.* But this can change depending on the time of year, airline and other factors.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from O'Hare Intl. Airport (ORD) to Havana (HAV-Jose Marti Intl.)?
To avoid potential delays on the O’Hare Intl. Airport (ORD) to Havana (HAV-Jose Marti Intl.) route, fly before 3 PM. Flights after this time are 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.
Is it cheaper to buy a plane ticket from O'Hare Intl. Airport (ORD) to Havana (HAV-Jose Marti Intl.) last-minute?
Last-minute fares from ORD to HAV are generally more expensive. For the lowest rates, start looking for flights well ahead of time. That being said, if you can play around with your travel dates, you may land a cheap ticket right before your journey.
Can I cancel or change the date of my flight from O'Hare Intl. Airport (ORD) to Havana (HAV-Jose Marti Intl.)?
If you reserved your ORD to HAV flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond that time. Airline policies and contact information can be found in your itinerary or confirmation email. Or, go to our Customer Service portal for more information.

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*Available to One Key members.