Flights from Chicago (MDW) to Miami (MIA)

Get ready to wing away from the Windy City to sunny Miami. Find cheap flights from Chicago Midway International Airport to Miami International Airport and start planning for fun in the sun. If you have flexible travel dates, remember to explore the Low Fare Calendar to see the cheapest available tickets inside your travel window. Make the most of your reservation with package deals on flights, hotels, rental cars, and more from Southwest Vacations®.

See what makes Miami the Magic City—book your next flight with Southwest today.

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Chicago (Midway), IL to Miami, FL

departing on 12/18

one-way starting at*

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*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 65 travel days available.

Check out Chicago (Midway) to Miami flights and book yours now!

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Travel Advisory

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.

Flight details

Average flight time: 3 hours 15 minutes

Departing from: Chicago Midway International Airport (MDW)

Arriving at: Miami International Airport (MIA)


Route information


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Based on DOT published scheduled average flights Monday-Friday between 10/30/2020 and 12/31/2020, as of 11/2/2020.

Explore Miami

Miami is on the scene when you deplane at Miami International Airport. Don’t get us wrong—Chi-town’s got it going on, but Magic City has an energy you can’t get anywhere else. A trip to Miami is about more than fun in the sun—hop on a bus or train, call a rideshare, or rent a car and start exploring. Whether you’re planning a group trip to say, “thank you for being a friend,” a romantic getaway for two, or a whole-family outing, there’s something for every visitor in this eclectic oceanside city.

Dive right into learning about Miami and greater Florida with a visit to HistoryMiami, the largest history museum in the state. Here, you’ll find a permanent exhibit that traces 12,000 years of the area’s history, making it a jam-packed way to spend an afternoon of your visit. After you’ve had your fill of historical context, take a bite of something else that makes Miami unique: Floribbean cuisine. An organic fusion of Caribbean, Hispanic, and Asian cuisines brought to the region by large immigrant communities, Floribbean cuisine relies on fresh seafood and assertive spices. Hungry for something else? Seek out a Cuban sandwich, which some believe originated in town rather than elsewhere in South Florida.

While you may feel familiar with the city, thanks to its frequent portrayal in TV shows, movies, and songs, it’s no surprise that Miami is among the top stateside destinations for tourists. The eclectic tropical vibes just can’t transcend song or screen. Whether you yearn to see the moon over Miami while enjoying electric nightlife or prefer to worship the sun from a beach blanket, there’s plenty to do when you visit. See what you’ll conjure up during your trip to Magic City.

Travel tips


Infancy policy

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.


Pet policy

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.


Unaccompanied minor

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.


Bags fly free®1

Start packing! Every ticketed Customer’s first two checked bags are free. Learn more.


The Southwest® travel experience

It’s easy to say goodbye to the City of the Big Shoulders and hello to the Sunshine State when you book with Southwest. We work to make every step of your flight, from booking to boarding, as simple as possible so you can focus on enjoying your final destination. Learn more about what you can expect from the Southwest® Experience before you book your next flight from Chicago Midway International Airport to Miami International Airport.

Book your next flight to Miami with confidence—no hidden fees, reliably low fares, and bags fly free. That’s Transfarency.® Want to stay in the know about our latest flight and vacation package deals? Enroll in our Click 'N Save® emails. For more information on tours, activities, and more hidden gems, check out 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.

Questions we hear the most

How long is the flight from Chicago (Midway) to Miami?

The average flight time from Chicago (Midway) to Miami is 3 hours 15 minutes.

How many Southwest flights from Chicago (Midway) to Miami occur daily?

There are 9 flights daily from Chicago (Midway) to Miami on Southwest Airlines.

Does Southwest fly nonstop from Chicago (Midway) to Miami?

Southwest flies nonstop from Chicago (Midway) to Miami once daily.

What day is it cheapest to fly from Chicago (Midway) to Miami?

To find the cheapest day and time to fly Chicago (Midway) to Miami with Southwest, check out our Low Fare Calendar.

Can I rent a car at Miami International Airport?

You can rent a car at Miami International Airport—book yours with your flight.

Can I change my flight reservation for my flight from Chicago (Midway) to Miami?

Yes! Flights from Chicago (Midway) to Miami—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 Miami?

Check the status of your upcoming Southwest flight here.

Where can I find answers to other questions about flying from Chicago (Midway) to Miami with Southwest?

Check out the Southwest Airlines® FAQs for answers about everything Southwest.