We introduced the PointsAway Award Odometer a couple weeks back and already have a few new notes to add based on recent bookings. Here’s the latest, and how we booked each:

Weekend in Philadel…I mean, Atlanta

My brother will be in Atlanta for a couple weeks on work, and invited me to meet him there for the weekend in between his two work weeks. I agreed, after seeing tickets from JAX to ATL available for only around 5,800 Rapid Rewards points each way on Southwest.

Needless to say, I was upset when I checked back two days later and the price had risen to 8,204 points each way! While dropping 11,600 points for a weekend trip was palatable to me, I had a hard time justifying an expense of 16,408 points – or the equivalent in dollars – for a trip that would scarcely last three days. I was certain there had to be a better way, especially knowing how Southwest schedules its flights out of Jacksonville with many destinations connecting through Atlanta.

I decided to see if taking advantage of hidden city pricing would be possible on this itinerary, and I was shocked by what I found. This is a concept we haven’t discussed before at PointsAway, but one that’s fairly easy to understand. Sometimes, airlines charge more for a flight to a hub than they do for a flight connecting through a hub. In this case, that meant there was a chance the flight from Jacksonville to Atlanta was pricing at a more expensive rate than a flight from, say, Jacksonville to Chicago, Boston, New York or a variety of other destinations that connected through Atlanta along the way.

Airlines play these pricing games in order to better exploit demand between particular city pairs, but it can be an infuriating technique given that it effectively costs less to fly farther when hidden city pricing is in effect.

The way around this is simple, though not without risks: simply find a flight connecting through the city you’d actually like to travel to, and don’t take the connecting flight. Obviously, checking bags is out of the question in such a case, as your bags would continue on to the “final destination” even if you don’t! Secondly, if you miss a connecting flight, the rest of your itinerary will almost certainly be cancelled, so this trick only works on one-way journeys where a return is booked separately. Finally, many airlines specifically prohibit this in their contract of carriage, and may even void your frequent flyer account if you repeatedly break this rule!

Thankfully, Southwest’s program is one of the few to simply not mention hidden city pricing routes whatsoever. In past years, the airline’s contract of carriage even explicitly permitted knowledgeable flyers to take advantage of these pricing phenomenons. That means there’s little harm to taking advantage of this trick once in a while on Southwest.

Sure enough, after a few minutes of searching, I discovered this pricing discrepancy. On the day I’m looking to travel, here’s a look at the flight from Jacksonville to Atlanta:

Meanwhile, here’s an itinerary from Jacksonville to Philadelphia:

Notice anything interesting about this flight? It begins with the exact same flight to Atlanta, though it theoretically continues on to Philadelphia from there. The cost is about 40% less despite consisting of another flight, due to the games Southwest is playing on price!

At 4,967 Rapid Rewards points, this flight is now even cheaper than the one I initially had hoped to book. Because Southwest doesn’t levy any change fees, I’ll keep checking back and if a true direct flight from Jacksonville terminating in Atlanta opens up at this rate or lower, I’ll change my booking accordingly. Otherwise, I’ll simply walk off at Atlanta, let the gate agent know I won’t need to continue on to Philadelphia, and head on in to Atlanta.

For my return flight, I booked a cash fare to Orlando for $129 on Delta. I chose this route because I’m planning a fun feature from Atlanta’s Hartsfield Jackson airport on the day of my return flight, so you’ll see what all that is about in a few weeks.

Return from Pioneer Nation

I was vexed for the past month about what to do about my return flight from Pioneer Nation coming up at the end of March. While I was able to score a good flight from Southwest for just 10,680 points from Jacksonville to Portland, taking the same route home was going to require in excess of 16,000 points!

I simply wasn’t willing to part with that many, given I could book a return via American for just 8,750 AAdvantage miles using one of the Citi Reduced Mileage Awards available when heading to Jacksonville, but not on the way to Portland. However, I didn’t particularly want to use AA miles at all, since I’m in the process of saving up as many as I can for some future adventures.

Because I’d be heading out on a Saturday, I started taking a look at where I might spend a few days in order to lower the cost burden of the flight. While simply staying in Portland was an option, I had a better idea:

Vegas.

PDX-LAS

I love Vegas, and any good reason to go is welcome news. Vegas served me well as a stopover on the way home from Portland when I was last there in August of 2013, though that stop was by choice and less by need. I had a few thousand Virgin American Elevate points laying around and knew that this airline – a favorite of mine I get to fly rarely due to my Southeast locale – was currently having a sale on West Coast fares.

Sure enough, I found a route from Portland to Las Vegas by way of San Francisco that came in at just 3,535 Elevate points. I was just under 1,000 Elevate points short, so I transferred 2,000 Membership Rewards points from American Express at a 2:1 transfer ratio in order to make up the difference.

Just like that, my flight to Vegas was secured for a grand total of $5, with the majority of the cheap fare being covered by miles that would have likely otherwise expired a few months later unused.

Staying in Vegas

While in Vegas, I’d obviously need somewhere to stay. While I normally am able to find a great deal with MGM Grand, my Mlife rates failed me for once, with a prohibitively expensive charge for Saturday night of over $160 with more reasonable (for Vegas, where room rates are traditionally quite low) rates of roughly $45 per night for Sunday and Monday. I’d already identified a returning flight for Tuesday, hence my three night stay.

I wasn’t pleased with this rate, so I began searching around and found a new booking site called TravelPony.com. This site offers a sign-up bonus of $35 good toward your first booking! Additionally, a limited time promo code for an extra $50 off was floating around the night I was making my booking.

I checked TravelPony and found a Deluxe King Room at the Hard Rock for just $268.99 for all three nights. This rate was initially comparable to the rate at MGM, but after applying the coupon code and sign-up bonus, my total for all three nights fell to $183.99!

Even better, I paid using my Barclaycard Arrival because I had $100 in free travel credit available on the card. That lowered the price for my three night stay to only $83.99, or less than $28 per night!

At this point, I realized that not only was staying in Vegas for a few nights in order to catch a cheaper flight cost comparable to flying straight home: it was cheaper.

LAS-JAX

As I mentioned, I’d already found a cheap flight home from Las Vegas on Southwest. Requiring just 6,586 Rapid Rewards points, this flight was nearly 10,000 points less than a flight directly back to Jacksonville leaving Portland on Saturday.

I transferred Ultimate Rewards points from my Sapphire Preferred and booked the flight for $5 a few minutes later.

This is my favorite kind of award booking: one that doesn’t simply get you from one place to another, but adds value along the way. I’d have no business booking a separate trip to Las Vegas any time soon, but through clever use of miles and snatching up a good cash hotel rate, I created a three day stopover in one of my favorite cities in a way that saves money compared to staying in Portland and saves more than 10,000 points versus simply flying home directly.

It’s no surprise, then, that I couldn’t help but reinvest some of my savings: I’ll be seeing Elton John at Caesar’s and Penn & Teller at Rio while in town!

For this update, we didn’t include the flight back from Atlanta to Jacksonville, but dutifully included the rest, adding 3,049 miles and 3 nights to our running total! More to come as 2014 progresses.