Tag Archives: Award Travel

Want to Track Southwest Airlines Reservations for Price Drops? Try Southwest Monkey!

Don’t you just hate it when you leave money on the table? OK, maybe hate is too strong of a word, but would you rather have money in your pocket or give the airlines more money than you need to? We all know that airline ticket prices fluctuate, and so do the airlines! They don’t make it easy for us to catch the price drops and then rebook our tickets at lower prices. That brings us to Southwest Airlines, which has built a community by being different from other airlines.

Southwest Airlines has never allowed other websites to show their fares. They’ve always chosen to be the only sales outlet for their own flights. This means they are able to track and create a uniqueness in the way they serve Southwest Airlines flyers. I’ve read that some industry experts feel that it’s because Southwest Airlines does not always deliver the lowest fares all the time that they prefer to stay out of the comparisons. Instead, they provide an “everyday low price” value proposition. This could likely be the case, though in many markets, Southwest Airlines prices can actually be higher than full service carriers.

Southwest Airlines also distinguishes itself in that if your ticket price drops, both for paid flights and flights booked with Southwest Airlines points, you’ll get back the difference in the fare price. The process isn’t complicated, but YOU have to do the fare price checking and then of course, rebook the flight.

I like the expression “time is money” because I often find it to be true, especially in the miles/points world. I apply my “time is money” thinking to booking my award tickets with Juicy Miles. I often feel like spending some money to save both time AND money is a double win. I’ve had my frustrations with Southwest Airlines rules and regulations that’s for sure. So anything I can do to save me from having to check for price drops on Southwest Airlines is a win for me.

Enter Southwest Monkey. It’s a relatively new alert service available only for Southwest Airlines. Their website is simple and easy to use. You set up alerts on all the Southwest Airlines tickets you’ve booked and if the price drops, you’ll receive an email alert. If the price drops by more than $10, you’ll be charged their $3 fee. You rebook the Southwest Airlines flight yourself. This takes the pain point out of the equation because you no longer need to fuss about getting the lowest fare possible, and secondly it’s no longer necessary to continually check your Southwest Airlines fares for savings.

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Bye Bye Paper! United Airlines Club Passes Have Gone Digital

You might recall from a few months ago that I went to the San Diego Airport to gift my expiring United Airlines Club passes to two lucky people who just happened to be in the right place at the right time. It was a fun way to spend a few hours, and it mostly went smoothly! Looks like United Airlines has gone the digital route with these club passes as of November 2017.

Here’s the letter I received. You’ll notice that United will now be automatically adding these passes to our accounts within four weeks of our Chase United MileagePlus Credit Card anniversary date.

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Say Hi to Grant at the Chicago Seminars Travel Conference this Weekend (October 20-22)

Good afternoon everyone.  This weekend, October 20-22, I will be at the world famous Chicago Seminars in beautiful Chicago Elk Grove, Illinois (near Chicago O’Hare International Airport).  I love going to travel conferences, especially the Chicago Seminars.  It is great to see so many familiar friends, both readers and bloggers alike.  I will be there from Friday afternoon through Sunday evening wearing my Travel with Grant shirt.  If you see me, please stop by and say hi.

Every year, I go to several travel conferences and wear my Travel with Grant shirt, so I am very easy to spot.  But I always get emails the Monday after the event saying something along the lines of, “I saw you at the travel conferences and wanted to say hi, but I was too shy.”  Please don’t do that, if you see me, or any other travel blogger that you recognize, please stop and say hi.  We are there to meet and talk to you.  You flew or drove all the way to the travel conferences, so you just have to go the last 5-10 feet and make an introduction.  Trust me, it is worth the initial awkwardness (everyone feels like that at their first travel conference).

While you are there, keep a lookout for this guy pictured below.  His name is Ray and he knows a thing or two about churning credit cards. I hope to see some of you this weekend.  Safe travels everyone.

Grant and Ray @ Chicago Seminars (October 2014)

Find the Perfect Routing for your Next Award Flight

Do you have all the time in the world to keep track of all the airlines, the alliances, which airlines are adding flights and routes, and which routes are being canceled? I certainly don’t. I was reminded of this a few weeks ago when United announced its new non-stops to Europe for Summer 2018. Sure, these are seasonal routes, but still, for those of us who work hard accumulating miles and points, this is exactly the kind of knowledge we need to book those award tickets, and book them early. Knowing when award charts open, and seasonal route award seats are bookable, is just not something I’m good about keeping track of. In addition to United’s new Summer routes, United also started daily service between LAX and Singapore and between New York and Buenos Aires. See what I mean? That’s a lot of news to follow. And that’s just United.

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Caroline Lupini: An Introduction

Well, in typical Caroline fashion, I got too excited about writing a travel related post and completely forgot to introduce myself!

So hey, nice to meet you!

I’ve been around the points and miles world for a while, so perhaps you’ve seen my name somewhere. I used to write a blog on Boarding Area called Point Princess, but I wanted to expand my blogging topics beyond points and miles, so I started an über creatively named site called Caroline Lupini.

Since then, I definitely haven’t slowed down on the points and miles writing, but I’ve also had some fun writing a few destination pieces too.

Overall, my goal is to travel as much as I can. I have the luxury of working online, so I spend about half of the year outside of the U.S. I’ve been to 70 countries so far, and I hope to one day visit them all. I really enjoy off-the-beaten-path destinations like Iraqi Kurdistan, Algeria, and Myanmar, and I’m super excited about my upcoming trip to Iran!

Virtue is concerned with what we do, and honor is concerned with how we do it. -Gregory David Roberts 📸@forrestlin90

A post shared by Caroline Lupini (@caroline.lupini) on

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