Posted in Airlines

Flying with Southwest Airlines

This year I plan to fly a lot on Southwest Airlines because I have a Companion Pass and a pile of miles to use.  To start this years travel season, I set my daughter as my Companion.  We just flew from Michigan to Portland, Oregon for my first trip of the year.  $316 Round trip total for the 2 of us!

After we got back, I called Southwest and changed my Companion from my daughter to my husband for the duration of the year (although I could technically change it one more time if I wanted to).  Now I am able to start making reservations for our trips together.

Mark and I are planning some trips to Texas for A&M football games (which means we get to visit our son too), but we would also like to take a relaxing late fall beach vacation.  Now that Southwest has added Hawaii to it’s routes, we will have to consider it as one of our potential destinations along with these other great getaway locations.

Some Southwest Getaway Locations

  • Havana, Cuba
  • Aruba
  • San Juan, Puerto Rico
  • Hawaii
  • Punta Cana, Dominican Republic
  • Grand Cayman
  • Montego Bay, Jamaica
  • Nassau, Bahamas
  • Turks & Caicos
  • Puerta Vallarta, Mexico
  • Cabo San Lucas, Mexico
  • Cancun, Mexico, Mexico


My Thoughts on Southwest Airlines

Love It

  • 2 Bags fly free
  • Economical Fares with frequent sales
  • They Fly to and from my home airport (DTW)
  • No Cancellation or Change Fees
  • Good selection of inflight entertainment for streaming on your personal device

Just OK

  • List of cities they fly to
  • Quality of the seats
  • Cleanliness of the planes
  • Rapid Rewards Program is pretty good but could be a bit more robust
  • Even after paying the fee for Early Bird Check in, you still don’t get to pick your seats and are not guaranteed an A group boarding position

Hate It

  • No plugs or chargers to power your devices at your seat
  • Fare calendar needs to go further out
  • If my boarding position isn’t high enough, I could be stuck seated separately from my travel companion (my first flight with SW a few years ago, Mark and I were separated and I ended up squished in a  middle seat between 2 very large gents all the way to TX).


How I Prepare for a Southwest Flight

  • Either pay for the Early Bird Check in or make sure to check in as soon as we are allowed. (If I pay for the Early Bird Check in with my Amex Gold Card, they reimburse it as an “Airline Fee”).
  • I know to grab a snack before I board the plane.
  • Since there are no chargers, I try to make certain all my devices are 100% charged.
  • With no seat back entertainment, I pack magazines or travel guides to read. I find planes too distracting to sleep or do any serious reading.


I am a deal seeking budget traveler! Southwest works for me because they are an Economy Carrier and I get what I pay for and what I expect. No frills just an affordable way to fly and stretch my travel budget a little further.

So far, I have been fortunate that all my flight experiences have been smooth, on time and I haven’t had any real issues. I consider Southwest to be a reliable and dependable carrier and feel comfortable using them for air travel.  Even after my Companion Pass ends, I will continue to use them for my domestic air travel because I think they are a good value.





Just an Art and History Nerd from MI Who Loves to Travel, Explore, Save Money, Share Tips, Enjoy the Best Foods & Adult Beverages🍷🥂🍸 Then Blog About It!