Southwest Airlines is proud to serve Chicago Midway International Airport.
Boarding a Southwest flight departing Midway is a snap—just hop on the “L” train! The Orange Line will take you directly to the airport, the first stop on your adventure beyond the Second City. Of course, long-term parking and calling a car are always options, too.
A world-class city like Chicago has something for everyone and pockets of cultures from around the globe, but it doesn’t have everything. Ocean views? Not one, though Lake Michigan is lovely. Mountain peaks? The only heights you’ll find among the flat terrain of this Midwestern hub are skyscrapers. Dry desert heat is of course unheard of—that lovely lake sure does make it plenty humid in the summertime. There’s so much world out there to explore beyond the Chicagoland area, and Southwest can take you there. And since Chicago Midway International Airport is a Southwest Airlines hub, many of those flights out of Chi-Town are direct!
It’s time for a change of scenery. Take a break from the hustle and bustle of big-city life (or trade Second City vibes for the buzz of another metropolis) with a flight on Southwest Airlines. Whether you choose an oceanside getaway, a desert retreat, or to disappear into another walk of life entirely, Southwest can take you there from Chicago Midway International Airport. Discover all your destination and flight options and rack up those Rapid Rewards® points when you fly. Know your booking process will be straightforward from flight selection to checkout to boarding. Learn more about what makes the Southwest® Experience different.
Experience otherworldly theme parks or enjoy the down to earth vibes in this Central Florida city that’s the perfect steppingstone for once in a lifetime day trips.
*Fares are updated hourly. Fares displayed on external channels may no longer be available at time of booking. To find the most updated fare, please visit Southwest.com. Restrictions and exclusions apply. Seats and dates are limited. Fares may vary by destination, flight, and day of week and won't be available on some flights that operate during very busy travel times and holiday periods.
Got flexible travel plans?
Use our Low Fare Calendar to find the lowest fares on flights from Midway available inside your travel window.
Cities with daily nonstop flights Monday through Friday from MDW
72‡
Cities with daily nonstop flights Saturday through Sunday from MDW
73§
*Fares are updated hourly. Fares displayed on external channels may no longer be available at time of booking. To find the most updated fare, please visit Southwest.com. Restrictions and exclusions apply. Seats and dates are limited. Fares may vary by destination, flight, and day of week and won't be available on some flights that operate during very busy travel times and holiday periods.
†Weekly flights based on DOT published scheduled average flights Monday through Sunday between 3/1/2025 and 3/31/2025. Note: route may not operate every day of the week.
‡Nonstop flights based on DOT published scheduled average flights Monday through Friday between 3/1/2025 and 3/31/2025.
§Nonstop flights based on DOT published scheduled average flights Saturday through Sunday between 3/1/2025 and 3/31/2025.
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