Southwest Airlines Finally Makes It Great To Fly Them Out Of Orlando

Southwest Airlines may not be the low-cost carrier they once were, but you can still find plenty of really cheap flights on their website.  Orlando is one of the routes from my home of Washington, DC that’s traditionally dirt cheap.  It’s not unheard of to see $20 one-way fares between DC and Orlando even at peak travel times.  But, Southwest is almost impossible to fly out of Orlando if you have a checked bag.  Well, they used to be.

Just to be clear, my checked bag strategy of having the airlines pry my bag out of my cold, dead hands hasn’t changed.  However, Orlando always involves two things for me, kids and souvenirs. That can sometimes make checking a bag a necessity.

Our most recent trip to Disney World wasn’t much different from previous Southwest flights.  After dealing with unbelievably predatory pricing for a few gallons of gas, we were showing up to the airport just over 2 hours prior to our flight to check a bag.

Even though we’re frequent visitors to Disney World I was still surprised by the line to check bags outside.  I asked Michelle to stand in line outside with the bags and kids while I checked what the line inside looked like.

Hard to believe, but the line inside was worse.  I asked people near the front of each line how long they had been waiting.  Folks outside said almost 90 minutes while the people near the front of the inside said it had been closer to 2 hours.  There was an outside chance that we could still make our flight if we waited 90 minutes to check our bags.  However, considering my disastrous afternoon at Disney World the day before (nothing like having a crowd watch you get violently ill in front of Tomorrowland Speedway) I didn’t have near enough energy to stand in a line for 90 minutes and then make a run for the gate.  Heck, I wasn’t even really confident we could make it.

The line bent around behind where I was standing as well

The moral of the story that day was that I got in the much shorter Business Select line to purchase upgrade so we could check our bags in time.  An unbelievable Southwest employee took pity on me (I must have looked pretty horrible) and checked our bags without charging me for the upgrade.

Change For The Better

Fast forward to our Disney World trip last month.  The airport is dealing with some construction.  Part of that construction is the renovation of the ticket counters.  Boy, is Southwest taking advantage of the renovation!  I was in the airport in the evening waiting to pick my family up.  I had flown down a few days earlier for a business trip.  It was easy to notice the drastic changes to the Southwest check-in area.

There are now dozens of kiosks where customers can self-tag their bags!  It was late at night and there weren’t that many passengers milling around.  Would the check-in kiosks be enough to stem the flow of a real crowd?  I asked a few employees standing around what they thought.  They said that they hadn’t seen lines longer than 20 or 30 minutes to use a kiosk.  Further, most days they said there was barely a line.

The true test of their statements would be on our return flight a few days later.  We showed up around the same time of morning as our previous trip.  I wasn’t expecting long lines, but I was expecting some sort of line.  Nope.  We walked right up to a kiosk and tagged our bags.  The whole process took less than 5 minutes.

The Final Two Pennies

We have yet to see the new setup during spring break, where Orlando airport represents a slow motion version of the bulls at Pamplona.  But, I’m pretty confident the days of 2-hour waits at Orlando to check a bag are a fading memory.  The airport still has some work to do on wrestling down long security lines.  Until they solve that, Clear or TSA Pre-Check can magically turn the busy airport into an easy trek with Southwest’s new bag check area.

The post Southwest Airlines Finally Makes It Great To Fly Them Out Of Orlando was published first on Pizza in Motion


  1. Completely agree with your assessment. We go to MCO a lot and I have always dreaded the bag check leaving MCO. During Christmas of 2016, the line was so long that we thought we had just gotten in line for the seven dwarfs mine train again. Fast forward to Christmas 2017 – wow! There were empty kiosks when we approached. It took 3 minutes and we were on our way. I won’t hesitate to bring my golf clubs to MCO next time. Thank you Southwest!

  2. I would love to say they have just added these kiosks to TPA as well, but like you, I rarely check a bag, so I don’t know how long TPA has had them, but we used them last month on the way out of town, so it was certainly nice. Of course I messed up applying the tag, but it still worked.

  3. This is good news. Those lines are the primary reason I do not think I’ve ever flown WN out of MCO. Just booked a flight out of there for July. Will hope for the best, especially since it’s on a Tuesday.

  4. I ended up on a last minute flight out of MDW in August, and they had just installed the kiosks. Since my boarding pass was on my phone, the kiosks (especially since I had two checked bags and two carry ons, long story) were a lifesaver. Then 10 minutes at TSA, regular line, and I was to the gate. ALB isn’t big enough to warrant these, but I’m glad the big airports are finding a way around the crowds.

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