A Whirlwind 50 Hour Trip to Chicago – Day 1

19553905_10154511663915974_1785449452011117391_nI’m writing this on the plane going back home from a short trip to Chicago. This was a shorter trip than Sharon and I would normally take so there had to be a good reason behind it. Just like our trip to New York in January, we traveled to Chicago because Sharon used her Ticketmaster skills to get us tickets to see “Hamilton.” Getting tickets for the show in Chicago was a little easier than for New York, but not much. To make things more complicated, we needed to change the dates of our tickets due to some conflicts that came up and then we had to shorten the rescheduled trip due to other commitments. Thank goodness I booked the original airline tickets with Southwest so I didn’t have to pay to change the flights. Even with it being a short trip and all the changes we had to make, we had a blast and are so glad we went.

Knowing we had such a limited amount of time to see the city, we narrowed down what

Continue reading “A Whirlwind 50 Hour Trip to Chicago – Day 1”

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My Experiences When Changing or Cancelling a Flight on Southwest Airlines

I’ve written before about how much we’ve traveled on Southwest recently and even how we haven’t paid for a flight on Southwest Airlines since 2015.  Well, the time eventually came when I had to book a ticket on Southwest with cash instead of miles. I just didn’t have enough Southwest miles left to cover the cost of the flight for both of us on this trip.

Southwest_Canyon_Blue
Photo By Brian from Toronto, Canada – Southwest 737, CC BY-SA 2.0, https://commons.wikimedia.org/w/index.php?curid=2271529

17761038_1121957987914685_4477871181367452954_oWe are flying to Chicago for a weekend to see Hamilton  (Again. Don’t hate us.) and I know I cleared these dates with Sharon before I booked the airline tickets. But sometimes life happens and plans change. This time we needed to change our travel dates because Sharon was cast in the choir of Encore!  for their upcoming production of Hairspray at the Dr. Phillips Center in Orlando (shameless plug – tickets are on sale here).  This did cause a bit of a dilemma as Sharon now has a rehearsal scheduled for the day we were going to be flying to Chicago, and that just wasn’t going to work.

When we realized this, I immediately was relieved because I knew I had booked the Continue reading “My Experiences When Changing or Cancelling a Flight on Southwest Airlines”