Get ready to wing away from the Windy City to sunny Miami. Find low fares on 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 lowest available fares 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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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 COVID-19 Travel Information page for information about potential restrictions on air travel.
Departing from: Chicago Midway International Airport (MDW)
Arriving at: Miami International Airport (MIA)
Other popular flights from Chicago (Midway)
View our interactive mapMiami 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.
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 Miami 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 Miami the best it can be. Learn more about the Southwest® travel experience before you book your flight from Chicago Midway International Airport to Miami 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 Miami, 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®1. Want the latest news, information, and promotional offers from Southwest? Sign up to receive email from us. Looking for tours, activities, and more hidden gems to add to your Miami adventure? Explore getaways with Southwest®. Book your flight today and know that you'll earn Rapid Rewards® points when you fly.
1First and second checked bags. Weight and size limits apply.
2Fare difference may apply.
To find the lowest fares by day and time to fly Chicago (Midway) to Miami with Southwest, check out our Low Fare Calendar.
You can rent a car at Miami International Airport—book yours with your flight.
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.
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