Traveling from Midway.

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.

Other airports in the Chicagoland area.

Want to depart from another airport Southwest serves? Consider booking a flight from Chicago O'Hare International Airport.

Where you can fly from Midway.

Plan your ideal trip from Midway.

Dallas (Love Field)

Get ready to be wowed by the Big D! Dallas does everything big and they do it well—from blues to leading a herd of bronze steers.

Read more about Dallas (Love Field)

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.

Read more about Orlando
Los Angeles (LAX)

Experience the sparkle of Tinseltown—jet off to the West Coast for a visit to Los Angeles (LAX).

Read more about Los Angeles (LAX)
Las Vegas

Jet off to America’s Playground! When you travel to Las Vegas, having a good time is a sure thing.

Read more about Las Vegas