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Flights from Miami (MIA) to Chicago (MDW)
See what makes the City of the Big Shoulders stand so tall. Find cheap flights from Miami International Airport to Chicago Midway International Airport and start planning to experience a city that’s got it going on. 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®.
Trade fun in the sun for a helping of Midwest nice mixed with big city hustle and bustle—book your flight.
Tripadvisor has rated us #1.
Best Airline in the U.S. and North America & Best Economy Class and Low Cost Airline in North America.
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 27 minutes
Departing from: Miami International Airport (MIA)
Arriving at: Chicago Midway International Airport (MDW)
†Based on DOT published scheduled average flights Monday-Friday between 1/29/2021 and 3/31/2021, as of 2/4/2021.
Explore Chicago.
Chicago may be the City that Works, but it plays just as well. When you deplane at Chicago Midway International Airport, grab a rental car, hail a ride, or board the Orange Line and head into the heart of the city to find your favorite way to play. While the train will take you directly into the Loop—what they call their downtown business district—there’s no need to spend your stay in this tourist favorite. Chicago is a city of neighborhoods, built of vibrant immigrant communities—see what you’ll discover.
Whether you’re a first-time visitor or have found Chicago to be a long-time favorite destination, everyone can find something new to learn at the Chicago History Museum. Founded in 1856, the museum calls the Lincoln Park neighborhood on the north side home. After your visit, consider stopping by Lincoln Park Zoo—one of the last remaining free-admission zoos in the U.S. If after you explore the fauna you crave some knowledge of flora, Lincoln Park is also home to the Peggy Notebaert Nature Museum.
If your sightseeing has helped you work up an appetite, there’s plenty to eat in the Lincoln Park neighborhood but why limit yourself? Whether you want to try the true Chicago-style pizza—thin crust, tavern cut, not deep dish—or indulge in Michelin-starred dining, there’s something for every craving waiting for you. From Restaurant Row to food trucks, get a taste of the city or one of the dozens of international cuisines that have made their mark on the local culinary landscape.
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
Let the Magic City lead you to the Second City—book your next flight 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 Miami International Airport to Chicago Midway International Airport.
Book your next flight to Chicago (Midway) 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 getaways with Southwest® 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
The average flight time from Miami to Chicago (Midway) is 3 hours 27 minutes.
There are 12 flights daily from Miami to Chicago (Midway) on Southwest Airlines.
Southwest flies nonstop from Miami to Chicago (Midway) once daily.
To find the cheapest day and time to fly Miami to Chicago (Midway) with Southwest, check out our Low Fare Calendar.
