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 check out exciting getaways with Southwest® —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.

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
 
Orlando

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
 
Los Angeles (LAX)

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

Read more
 
Las Vegas

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

Read more
 
Seattle/Tacoma

Whether you choose to explore Emerald City or Grit City, your adventure starts with a flight to Seattle Tacoma International Airport.

Read more
 
New Orleans

Enjoy some easy living or all night excitement down in the Big Easy. Just be sure to bring your appetite to this Southern belle of the ball.

Read more
 
Miami

Conjure up a beachy adventure with a trip to Magic City and see why it’s one of the biggest tourism hubs in the U.S.

Read more
 
Tampa

Take in the Sunshine State from this Gulf Coast city, the jewel of the Tampa Bay area.

Read more