Navy memorabilia at Chicago Midway airport, named for the WWII Battle of Midway in the Pacific (courtesy Ralph Paglia at Flickr CC)

Once a year, I fly into Chicago for the SOBCon online business conference.

The City of Broad Shoulders is magnificent and one of my favorites;  without pretension, relatively clean, full of spectacular architecture and world-class museums like the Art Institute with its Monet collection (and my personal favorite, Nighthawks.)

But lets’s talk about how to arrive in Chicago by air – via the Midway airport, if possible.

The big main aviation hub at O’Hare Airport is not bad, but it is much further outside the city. To use Midway, you’ll probably need to fly in on Southwest Airlines (although a few other carriers use the airport) but that’s OK with me because I like Southwest. Their crews seem to actually be happy with their jobs, and they don’t treat passengers as though we were inconvenient annoyances.

One year when I booked my flight to SOBCon, I had to leave Austin super-early in the morning and fly into Midway. At first I was pretty annoyed, but that’s when I discovered that by arriving so much closer in, with quick access to Chicago Transit Authority public transport options, I could be in the downtown Loop eating pancakes at Lou Mitchell’s by about 9:30 am, even if I took a quick spin around the Loop on the Brown Line of the El (elevated subway) to see the sights.

After breakfast, the whole day stretched before me, and I was already located in the thick of the action.

Moral of the story – never assume that all airports are the same. You could be putting a fine breakfast at risk.

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I'm a writer and speaker specializing in tourism, travel and social media. NHRA drag racing fan. Co-founder of Tourism Currents. U.S. Navy veteran. Caffeinated.