I am a pretty big fan of flying southwest when I am flying domestically. I love the flexibility of their program, I generally find their prices to be pretty competitive, and I think their service is at least on par with most other domestic carriers. Not to mention that by buying Southwest gift cards online, through Staples, I can usually get 7x UR points/dollar spent, and still earn the 1.67 cents/dollar spent towards future Wanna Get Away Fares.

When I was searching for flights for Charleston, they were running somewhere around $400 round trip from any airport I was willing to fly out of to CHS. I looked into flying into nearby airports down there, but due to timing restrictions that I thought I was going to have from work, there was nothing that I was able to make work. I wasn’t really interested in redeeming miles for this trip, either. So I just sucked it up… Southwest’s flights were hitting around that $400 mark as well, so I decided to fly with them. I ended up with a 2-hour layover at BWI on the outbound and a 3 hour layover at MDW on the inbound (and I’ll actually just be staying in Chicago for a few days and getting a ride home with a friend, as it turns out).

Fast forward a couple months… I am now not starting my full-time job until the following week, and I am looking at a school   out in Baltimore, in addition to having made a bunch of friends who live out that way on the 4K. I wanted to make the 2-hour layover at BWI longer. Initially, I looked into just flying in that morning. It originally added about $20 to my total ticket price, a price I was willing to pay to check out this school, since otherwise it would warrant another trip (not that I would complain about that). I really got to thinking though, and realized I should just go out to Baltimore for a few days! Check out the school and catch up with friends! It still only added about $20 to my trip price, and I didn’t really have to worry about hotels since I am staying with friends (although now I am checking out a Kimpton property while I am out there too). With the recent $69 Southwest sale, I was able to get $17 back for use on future Southwest flights… bringing my extra cost down to only $3! (plus the elective Kimpton stay)

I would say that was a great price for extending my trip for an extra three days. All I had to do was book the segments separately.

 

Another example of this working out well happened just recently for a friend of mine. One of my 4K friends, who is from St. Louis, was looking at coming to visit me at some point before school starts for him. He was debating between coming on his way out to school (in Baltimore), or going out to school and then flying to Michigan. The additional cost of flying into DTW and out of FNT was only $100, whereas it would have cost $180 for him to fly round trip between BWI and FNT.

 

If you ever have the option to string multiple trips together, this could be a great method of doing so to save a bit of money!