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Flights from Havana (HAV) to Chicago (MDW)
Book flights from Havana to Chicago (Midway) with Southwest Airlines®. It’s easy to find the José Martí International Airport to Chicago Midway 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 Havana to Chicago (Midway) flight with Southwest today!
This route has a travel restriction that may impact your trip.
Entry into the United States: The U.S. government is requiring anyone traveling into the United States to provide COVID-19-related documentation and contact tracing information. Visit our COVID-19 Travel Information page for more information.
*Weekly flights based on DOT published scheduled average flights Monday through Sunday between 5/1/2022 and 5/31/2022. Note: route may not operate every day of the week.
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.
The Southwest travel experience
At Southwest, we know it takes more than great deals on Chicago (Midway) 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 Havana to Chicago (Midway) the best it can be. Learn more about the Southwest® travel experience before you book your flight from José Martí International Airport to Chicago Midway International Airport.
Flying with Southwest is simple and fun, no matter which of our dozens of exciting destinations you choose. When you search for your next flight to Chicago (Midway), know that you won’t be surprised at checkout. Low fares and no hidden fees. That's Transfarency®. And as always, two bags fly free®3. Want the latest news, information, and promotional offers from Southwest? Sign up to receive email from us. Book your flight today and know that you'll earn Rapid Rewards® points when you fly.
1Available only on WiFi-enabled aircraft. Limited-time offer. Where available.
2Internet access for $8 a day per device on WiFi-enabled aircraft. Price is subject to change. May not be available full duration of flight. In order to provide a top-notch WiFi experience, we prohibit access to certain high-bandwidth applications and websites, including Netflix, HBO GO® and VoIP. We also prohibit access to certain obscene or offensive content.
3First and second checked bags. Weight and size limits apply.
4Fare difference may apply.
5Failure to cancel a reservation at least 10 minutes prior to departure may result in forfeited Travel Funds.
Questions we hear the most
There are 22 weekly flights from Havana to Chicago (Midway) on Southwest Airlines.
To find the lowest fares by day and time to fly Havana to Chicago (Midway) with Southwest, check out our Low Fare Calendar.