Where Does Southwest Fly To From Chicago

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So, You Wanna Get Outta Chicago? Let's Talk Southwest

Chicago, the Windy City. Great pizza, deep dish dreams, and a whole lotta people trying to escape the winter. If you're one of those people, and you're thinking of using Southwest to make your great escape, let's break it down.

Where in the World Does Southwest Fly From Chicago?

First things first, let's get this straight: Southwest flies out of TWO airports in Chicago: O'Hare (ORD) and Midway (MDW). So, if you're planning your getaway, make sure you know which one you're leaving from. Don't want to end up in the wrong terminal, looking like a lost puppy.

O'Hare (ORD): Your Gateway to the World (Or at Least a Good Chunk of It)

If you're flying out of O'Hare with Southwest, you've got a pretty decent selection of destinations. We're talking about cities like:

  • Las Vegas: For those who prefer their concrete jungles to the real ones.
  • New York (LaGuardia): The Big Apple awaits!
  • Orlando: Theme parks, sunshine, and overpriced souvenirs - what's not to love?
  • Boston: Clam chowder, history, and accents thicker than a Boston cream pie.

Midway (MDW): A More Compact, But Still Sweet, Selection

Midway might be smaller, but it's got its charm. You can catch flights to:

  • Denver: Perfect for those who crave mountains and wide-open spaces.
  • Phoenix: Embrace the desert heat and cacti galore.
  • Dallas: Tex-Mex, cowboys, and big hair - need we say more?

Tips for Flying Southwest Out of Chicago

  • Check Your Bags: Southwest used to be all about the free checked bags, but those days are sadly over. So, pack light or be prepared to pay up.
  • Early Bird Gets the Worm (Or the Seat): Want to board early? Get to the gate on time. Southwest's boarding process can be a bit chaotic, so being early is key.
  • Embrace the Randomness: Seat assignments? What's that? Southwest is all about the free-for-all, so don't expect to be sitting next to your travel buddy.

How to... Southwest Edition

How to choose between O'Hare and Midway?

  • It depends on where you live in Chicago and your destination. O'Hare generally has more flights and destinations, while Midway is often closer for those on the South Side.

How to get to the airport?

  • Both airports have public transportation options like trains and buses. You can also take taxis or rideshares.

How to survive a Southwest flight?

  • Bring your own entertainment, be flexible, and maybe pack some snacks.

How to find cheap flights?

  • Use Southwest's website or app, be flexible with your dates, and consider traveling on weekdays.

How to avoid checked bag fees?

  • Pack light, or be prepared to pay. You can also explore options like carry-on luggage or shipping your belongings ahead of time.

So, there you have it. Your Southwest guide to escaping Chicago. Now go forth and conquer!

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