See what makes the City of the Big Shoulders stand so tall. Find low fares on 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 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®.
Trade fun in the sun for a helping of Midwest nice mixed with big city hustle and bustle—book your flight.
Miami, FL to Chicago (Midway), IL
departing on 10/25
one-way starting at*$79
*Restrictions and exclusions apply. Seats and dates are limited. Select markets. 20 travel days available.
|Departing from||Miami International Airport (MIA)|
|Arriving at||Chicago Midway International Airport (MDW)|
|Average flight time||3 hours 5 minutes|
|2‡||Nonstop flights per day Monday through Friday|
|2‡||Nonstop flights on Saturday|
|2‡||Nonstop flights on Sunday|
†Weekly flights based on DOT published scheduled average flights Monday through Sunday between 10/1/2022 and 10/31/2022. Note: route may not operate every day of the week.
‡Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 10/1/2022 and 10/31/2022.
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.
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.
Chicago Midway International Airport is a quick 30-minute 'L' ride from downtown Chicago. Get going—adventure awaits.
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 Miami to Chicago (Midway) the best it can be. Learn more about the Southwest® travel experience before you book your flight from Miami 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®1. 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.
1First and second checked bags. Weight and size limits apply.
2Fare difference may apply.
3Failure to cancel a reservation at least 10 minutes prior to departure may result in forfeited Travel Funds.
4Flight credits unexpired on or created on or after July 28, 2022, do not expire and will show an expiration date until our systems are updated. See full details here.
5Available only on WiFi-enabled aircraft. Limited-time offer. Where available.
6Internet access for $8 a day, per device. In order to provide the best experience, we block access to certain high-bandwidth applications, websites, and video conferencing services, including, but not limited to, Netflix, HBO Max, Zoom, and Microsoft Teams. In consideration of the public environment onboard, we also block potentially offensive online content.