Where Does Southwest Fly From Chicago

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So, You Wanna Fly Southwest Outta Chicago?

Let's talk turkey, or should I say, let's talk Southwest flights from the Windy City. Chicago, a city renowned for deep-dish pizza, towering skyscrapers, and... surprisingly, a decent airport situation for Southwest.

Midway or O'Hare: The Age-Old Question

First things first, where are you flying out of? Chicago has two major airports: Midway (MDW) and O'Hare (ORD). Think of it like choosing between pizza and hot dogs – both delicious, but entirely different experiences.

  • Midway: This is your classic underdog story. Smaller, more manageable, and often with less hassle. Perfect for those who prefer a more intimate airport experience.
  • O'Hare: The big leagues. More flights, more people, and more opportunities to get lost (just kidding, kind of). If you're a frequent flyer or love a bit of chaos, O'Hare might be your jam.

Where Can You Actually Go?

Southwest has a pretty decent route map from both Chicago airports. You're not exactly limited to your neighbor's backyard. Expect to find flights to popular destinations like:

  • Beach Vacations: Think Florida, California, and the Caribbean.
  • City Escapes: New York, Los Angeles, Denver, and more.
  • Mountain Adventures: Colorado, Utah, and beyond.

Basically, if you can dream it, Southwest might just fly there.

Tips for Surviving Chicago Airports

  • Pack Light: Chicagoans are known for their layers, not their luggage.
  • Arrive Early: Especially during peak travel times. Chicago traffic is no joke.
  • Embrace the Deep Dish: Because, why wouldn't you?

How to...

  • How to choose between Midway and O'Hare: Consider the size of the airport, your preferred airline, and your destination.
  • How to find the best Southwest deals: Use Southwest’s website or a travel search engine to compare prices. Be flexible with your dates for the best savings.
  • How to survive a long layover in Chicago: Explore the city! There's plenty to see and do.
  • How to pack for a Chicago winter: Layers, layers, and more layers. Don't forget a warm hat and gloves.
  • How to enjoy a Chicago hot dog: No ketchup, ever. Trust us.
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