Book low fares from Chicago (Midway) to Havana with Southwest Airlines®. It’s easy to find the Chicago Midway International Airport to José Martí International Airport flight to make your booking and travel a breeze. Whether you’re traveling for business or pleasure, solo or with the whole family, you’ll enjoy flying Southwest®. Have flexible travel dates? Plug them into the Low Fare Calendar and see the lowest fares available within your travel window. You may also want to browse Southwest Vacations® to see special offers and package deals on flights, hotels, rental cars, and more.
Explore your options and book your Chicago (Midway) to Havana flight with Southwest today!
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Middle seats open through November 30
Full exchange of fresh, outdoor air every 2-3 minutes while inflight
Face coverings required
During the ongoing COVID-19 pandemic, the availability, health and safety procedures, operations, and schedules for local attractions are changing constantly. Please contact attractions directly for hours of operation, potential temperature screenings, and other possible health and safety procedures and restrictions. Visit our Coronavirus Travel Information page for information about potential restrictions on air travel.
Departing from: Chicago Midway International Airport (MDW)
Arriving at: José Martí International Airport (HAV)
Daily flight
Weekly flights
Flightbefore noon
Other popular flights from Chicago
View our interactive map*Based on DOT published scheduled average flights Monday-Friday between 10/30/2020 and 12/31/2020, as of 11/2/2020.
One child over 14 days and under two (2) years of age, not occupying a seat, may be carried free of charge when traveling with an adult (12 years of age or older). Learn more.
Customers flying with a pet are subject to a pet fare. To learn more about traveling with your furry friend, explore the Southwest® pet policy.
Minors under the age of 18 are not permitted to fly unaccompanied on international flights or any itinerary that includes an international flight. Learn more.
Start packing! Every ticketed Customer’s first two checked bags are free. Learn more.
At Southwest, we know it takes more than great deals on Havana airfares and convenient scheduling options to make your trip memorable. So from booking to boarding, we offer services and features designed to make your travel from Chicago (Midway) to Havana the best it can be. Find out more about the Southwest® Experience before you book your Chicago Midway International Airport to José Martí International Airport flight.
Flying with Southwest is simple and fun, no matter which of our dozens of exciting destinations you choose. And when you search for your next flight to Havana, you know you won’t be surprised at checkout. Low fares, no hidden fees. That’s our Transfarency® promise. And, as always, bags fly free. Enroll in our Click 'N Save® emails and stay up to date on our latest flight deals. Looking for tours, activities, and more hidden gems to add to your Havana adventure? Explore Southwest Airlines® Experiences and earn Rapid Rewards® points when you fly.
1First and second checked bags. Weight and size limits apply.
2Fare difference may apply.
How many Southwest flights from Chicago (Midway) to Havana occur daily?
There is one flight daily from Chicago (Midway) to Havana on Southwest Airlines.
What day is it cheapest to fly from Chicago (Midway) to Havana?
To find the cheapest day and time to fly Chicago (Midway) to Havana with Southwest, check out our Low Fare Calendar.
Can I rent a car at José Martí International Airport?
You can rent a car at José Martí International Airport—book yours with your flight.
Can I change my flight reservation for my flight from Chicago (Midway) to Havana?
Yes! Flights from Chicago (Midway) to Havana—or from here or there to anywhere—can be changed with no change fees. Fare difference may apply.
Where can I find the status of my flight from Chicago (Midway) to Havana?
Check the status of your upcoming Southwest flight here.
Where can I find answers to other questions about flying from Chicago (Midway) to Havana with Southwest?
Check out the Southwest Airlines® FAQs for answers about everything Southwest.
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