Pointing My Way to the (Online) Shopping Mall

Last week I ended up sleeping through Black Friday as I was nursing a serious turkey and pumpkin pie hangover.  Upon returning to the office, back-to-back “catching up” meetings kept me away from my computer.  Before I knew it, Cyber Monday had slipped by me as well.  The Holidays are upon us. I’m feeling seriously guilty about not doing my part to boost our economy. I should have been out there with everyone else partaking in a spree of rampant consumerism.

I know the shopping MUST get done. However, I’m loath to brave the crowds on Michigan Avenue. I’d much rather sit in the comfort of my own home in my boxers shorts, inhale a bag of Skinny Pop popcorn and mouseclick my way through my shopping “to do” lists as a marathon of Christmas-themed movies on Lifetime plays in the background. Of course, what would make things even better is if I was able to earn points the whole time I was doing this.

It is here where the concept of the online shopping portal comes into play.  Many of the major airlines maintain sites that enable the shopper to earn points by patronizing a variety of online retailers. In order to use a shopping portal, you simply login with your frequent flyer number, identify an online retailer that is of interest to you and “click through” to the retailer’s regular website where you complete the transaction as you normally would. The portal notes the transaction and awards you bonus points for the purchase.  Although you can use any credit card to make your purchase, you can maximize your Pointing by paying with your favorite awards earning credit card.  In other words, you would earn points from shopping through the portal AND points associated with the card that you are using.

Some of the major Airline Online Shopping Portals include the following:

American Airlines


















US Airways




Several of the airlines are also offering bonus points for channeling your purchases through their shopping portals:

American: Earn 500 bonus miles (up to a maximum of 2000 miles) for every $250 spent through December 17.

United: Earn 500 bonus miles (up to a maximum of 2500 bonus miles) for every $250 spent through December 31.

US Airways: Earn 300, 500 or a maximum of 1000 bonus miles when you spend $150, $250 or $500 through December 31.

Nevertheless, I realize that by shopping at home I am missing out on the camaraderie that arises when you cram large numbers of bargain hungry consumers into a confined space.  Therefore, in order to reproduce the “popular discount store” Black Friday experience I slept through last week, I plan on waking my Partner F at 3:00 am and making him stand in line in front of our refrigerator.   At 4:00 am as I open the door of our Sub-Zero, I will promptly body-check him as we both dive for the last bottle of Go-Go Mixed Berry Flavored Vitamin Water Zero.

Aaahh … I love the smell of a Pointing opportunity in the morning.  Happy Holiday Shopping everyone!

Frasier and Niles in Portland? Chicago – Portland for $178 Roundtrip on United

My Partner F and I have sometimes been described as the Frasier and Niles Crane of Chicago.  We enjoy fine restaurants, have a penchant for Mid-Century Modern furniture and have been known to take in an occasional performance of The Mikado at The Lyric.  However, as much as we enjoy having recreated our own version of that Seattle based sitcom here in the Midwest, we have come to realize that it’s time to freshen up our repertoire.

It seems that the epicenter of cool has shifted south from Seattle.  At least that’s what we’ve heard. We’ve become huge fans of the IFC series Portlandia. As a result, we are now considering fashioning ourselves after the various bohemian, artsy, foodie, techie, crunchy, lefty characters that populate this hilarious sketch comedy show.

Of course, in order to get properly into character F and I will need to take our act on the road to do some field research.  For the past several months we’ve been thinking of taking a trip out west to visit The City of Roses.  However, fares from Chicago to the Pacific Northwest have remained stubbornly high.

Therefore, I was thrilled when The Flight Deal reported today that Alaska Airlines we offering a fare of $178 roundtrip between Chicago and Portland.  Upon doing further research I discovered that United had matched the fare.  Here’s what availability looks like in January / February:

We’re thinking of taking a long weekend in order to make the best use of the Martin Luther King, Jr. Day (January 21) or Presidents’ Day (February 18) Holidays.  Here are a couple of potential itineraries:

These are some really great fares that have me tempted. Perhaps a trip to Portland might just be what I need to satisfy my latest travel urges.  In addition, could it be Kismet which is pushing us towards Portland?  Both of the cities I’ve been talking about in this blog entry have a common theme – they’re known for their great coffee.  Spooky, huh?

Oh wait a minute, neither F nor I drink coffee.  Oh well, maybe we’ll take in a microbrewery instead.

What’s In My Wallet – My Workhorse Cards

As I indicated in an earlier post, I am primarily a leisure traveler. Many of the frequent flyer points that I accumulate are earned not by “time in the air” but through credit card spending.  Over the last several years, the emergence of credit cards associated with pretty much every airline or hotel brand has provided the consumer with a multitude of Pointing vehicles and opportunities. In addition, credit card “Sign Up” bonuses can yield a healthy kick start to an average traveller’s mileage balances.

However, any discussion of credit cards must first start with a discussion of financial responsibility. I take a very conservative approach to my use of credit cards.  I always pay my balance off in full every month and keep a close watch on my credit score.  I take a very thoughtful and strategic approach to choosing the credit cards I apply for and the timing of when I apply for those cards. The maintenance a strong personal financial situation and responsible spending habits create a “virtuous cycle” that is very important part of an overall Pointing strategy.

There is an astonishing array of points earning cards available in the credit card universe. However, to get us started I’d like to give you a sense for “what’s in my wallet” and how I am using those cards as part of my overall Pointing strategy.  Please, bear in mind that I am very much of a “United Airlines guy” so that my credit card choices will have a MileagePlus / Star Alliance slant to them.

So how am I earning all of these points? Well, the answer is fairly obvious – instead of using cash, I try to pay for every financial transaction I conduct with a credit card.  By using a card that earns points, I am “monetizing” every purchase I normally would have made.  In addition, certain cards offer bonuses based on spending category

The following are the cards that I use on a daily basis.  They form the core of my Pointing strategies.

Chase Sapphire Preferred Visa

I just applied for this card in September and it has quickly become my favorite “everyday use” card.  What makes this card a cornerstone of my personal Pointing strategies is that it rewards me with 2X points in the categories that account for the largest portion of my personal spending – Dining and Travel.  For example, I use this card to pay for my monthly public transportation fare cards in addition to the taxis that I take when it’s raining and I’m too much of a wimp to wait for the bus.  I also receive double points on Uber – the on demand car service (more on this latest obsession of mine in a future post). Once I get to the office I’ll charge my morning bagel followed by mid-day slice of pizza and get double points as I do it.  The card earns 1 point per each $1 dollar spent on everything else.

Using this card earns Ultimate Rewards points which can be transferred on a 1:1 basis into the mileage programs of United Airlines, British Airways, Southwest Airlines and Korean Air.  Alternatively, you can transfer your Ultimate Rewards points into the loyalty programs of Marriott, Hyatt, Ritz-Carlton, Priority Club (Holiday Inn and Intercontinental) and Amtrak. Another great travel benefit of this card is that when any I book my travel through the Ultimate Rewards website I get 3 points for every dollar that I spend. In addition, the card does not charge you foreign transaction fees on any purchases that are made outside of the United States.

Finally, the Chase Sapphire Preferred will award you with a 7% Annual Points Dividend on all points that you have earned on purchases over the course of the year (including on points that you have redeemed for awards).  Signing up for this card will also give you a big boost of 40,000 Ultimate Rewards points once you have met the minimum spending requirement of $3,000 in the first 3 months of card ownership.

Chase United MileagePlus Select Visa

This is a card that I’ve had for several years now.  The Chase United MileagePlus Select Visa provides me with 3X Mileage Plus points on eligible United purchases.  However, the true value of this card is that I earn 2X points in such everyday spending categories as gas, home improvement purchases and dining.  However, what really makes this card a “keeper” for me is that I earn 2X points on all of my grocery purchase.  With Dining and Travel covered by my Chase Sapphire Preferred and Groceries covered by my Chase MileagePlus Select I have the overwhelming majority of my daily spending earning me at least double points.  Unfortunately, Chase no longer offers this card.  However, in a future post I’ll provide you with some ideas for other cards that can help you capture some additional value on that quart of milk that you just purchased at your local grocery store.

Chase United MileagePlus Club Card

Now that I have the Dining, Travel and Groceries categories covered, what about everything else? Not being the type of Pointer content to earn a merely a single point for every dollar I spend, I’ve turned to the Chase United MileagePlus Club Card to fill in the gaps.  The MileagePlus Club allows you to earn 1.5 MileagePlus points for every dollar that I spend.  The rest of my non-dining and non-travel spending goes on this card.  As with the Chase Sapphire Preferred card, foreign transaction fees are waived.

The card provides access to the United Club, the airline’s airport lounge network, in the U.S. as well as participating Star Alliance affiliated lounges overseas.  The card comes with Premier Access travel services which allows the cardholder to use the airline’s priority check-in, security, boarding and baggage handling services.  You and a companion are also allowed to each check two bags for free when you charge your airline ticket on the card.

However, this is a pricey card.  The annual fee is a whopping $395 ($95 statement credit after your first purchase).  That said, in my case I did the math in advance and found that my travel patterns are such that I can justify the cost of the card.  In particular, I travel a few times a year with my parents.  On those trips, the 3 of us always check our bags which alone nearly covers the cost of the annual fee.  In addition the Premier Access Travel services and Lounge Access make traveling through the airport with my elderly parents less stressful and more comfortable.

Another way to look at “what I get” with this card is that I have effectively “purchased” lower level Elite Status on United.  I get the same advanced boarding and travel benefits as MileagePlus Premier Silver members. What I do not receive are the 25% bonus miles, free access to Economy Plus preferred seating at check-in and the possibility of upgrades that come with Elite Status.  That said, I am still receiving double points on United purchases.  In addition, I can always “buy up” to Economy Plus if I’d like a little more legroom.  Finally, flying out of an “elite-heavy” hub like Chicago means that the possibility of upgrades for Premier Silver members may be limited anyway.

I have a few other cards in my Pointing arsenal that I use for other purposes and in specific travel scenarios.  I’ll talk more about those cards in future posts.  However, in terms of day-to-day credit card spending the Sapphire Preferred, MileagePlus Select and MileagePlus Club cards are my Pointing workhorses.

One last thing that falls into the “cool” category … the Sapphire Preferred and MileagePlus Club cards are issued in a “metal” material that is heavier than your typical plastic credit card.  I love a financial product that doubles as weapon and will pair nicely with my James Bond lifestyle and cat-like reflexes.  Oh but wait, that’s for a future post as well 😉

What kind of Pointer are you?

Update: There have been ALOT of changes in the Miles & Points world since I originally published this blog post. For an overview of what kind of Pointer I’ve become in 2015 please check out the update to this article here.

Wikipedia has this to say about a Pointer:

1. Anything that points or is used for pointing.

2. A needle-like component of a timepiece or measuring device that indicates the time or the current reading of the device.

3. A breed of hunting dog.

4. (programming) A variable that holds the address of a memory location where a value can be stored.

5. (computing) An icon that indicates the position of the mouse; a cursor.

6. A tip, a bit of advice (usually plural.) The instructor gave me some pointers on writing a good paper.

7. Something worth a given number of points. a ten-pointer 

To this definition I’d like to add:

8. A traveller who expresses a passion for the collection and redemption of loyalty award points; Pointing – process of collecting and redeeming loyalty award points.

Yes, I’m definitely a #8.  I’m a Pointer.  I’ve used airline and hotel reward points many times to not only get from Point A to Point B but also to enjoy travel experiences I would never otherwise have been able to afford.  Yes, points have allowed me to attain my travel goals.  Yet, it may seem to others that I’ve been a bit obsessive in my pursuit of points.  Rest assured my friends, there has always been a method to my madness.

Any discussion of points accumulation and the associated strategies for attaining those points needs to start with a close examination of one’s own personal motivations.  All of your efforts should really begin with a round of introspection and the asking of the question: Why?

I’ve found that the asking of the “Why” question helps the budding Pointer figure out not only the best ways to accumulate points but also the most effective ways to spend those points.  Moreover, the spending of points should go beyond what’s most “efficient” and should also factor in what would be the most valuable to you from a personal, professional and / or experiential perspective.

With these thoughts in mind, I think it’s important to ask yourself the following questions to help guide your Pointing strategies.  These are all questions that I have asked myself and they’ve proved very useful to me as I plot out strategy.  As you work your way through this questionnaire, I’ve provided my own answers so that you can start to get a sense for who I am and the thought process behind my Pointing strategies:

Why do you want to collect points?

I know that’s a ridiculously simple question.  However, unless you answer it you won’t have a starting point.  For example, should you be working towards an airline or a hotel reward or a combination of the two?

My focus is on airline points with my secondary goal being the accumulation of hotel points.

What kind of travel experience are you seeking?

Some people are just looking to get from Point A to Point B and traveling in economy is just fine.  Others are saving up for a Trip of a Lifetime. The answer to this question will determine just how many points you will need.  That number in turn will give you a sense for how much time you will need to accumulate those points.

I would fall into the aspirational award category. I’m currently saving up for a “Dream” Anniversary Trip to Thailand in 2015 for my Partner F and I.  Of course that sounds a LONG way off.  However, I’m hoping to earn enough points to fly to Asia in First Class on Thai Airways’ new A380 or perhaps stretch out in Asiana’s new First Class Suites. In addition, once I get there I’m hoping stay at the Conrad Koh Samui and a few other luxury hotels along the way.

That said, this trip will cost me at least 280,000 United Mileage Plus miles and 200,000 Hilton HHonors points for a 4 night stay on Koh Samui.  How am I going to earn all of those points? I’ll tell you how I plan to do this (and shave a few points off the points requirements) in future posts in my blog.

How much do you travel now?

Are you a Road Warrior who travels significantly for business?  Are you the occasional leisure traveler?  Have you never left your hometown? Travel provides the opportunity to earn the “currency” of award travel, the loyalty reward point.  Your current travel patterns will determine how much of this currency you have to reach your Pointing goals.

I don’t travel at all for business.  However, I do take 4-5 leisure trips a year which provides me with about 15,000 Mileage Plus miles annually. Given my travel patterns, flying alone will not allow me to reach my Pointing goals in the timeframe of when I would like to take my trip. I’ll need another way to earn those reward miles.

Where do you live?

The answer to this question helps determine who might be the best travel partners for you.  For example, do you live near one of the Major Airline Hubs?  For example, someone from Minneapolis, Detroit or Atlanta might best be served by aligning with Delta.  Someone out of Dallas might best be served by American Airlines.

I’m a Chicago guy who benefits from living near O’Hare so I have a great deal of choice with all the major carriers flying into my city.  In my case, I’ve aligned with my hometown airline of United.  Of course I do have frequent flyer accounts with all the major airlines and will fly American from time to time.  However, by declaring a “home” airline I’ll be able to focus my more limited time, travel and financial resources.  Of course, I’m never averse to opportunistic Pointing opportunities on other airlines as they arise.  All those points add up after awhile!

What’s in your wallet?

Credit cards have changed the landscape of the travel reward industry. Period.  These will prove to be a major tool in the Pointing strategies for most people.

Given that I won’t be relying heavily on time in the air to generate points, I will need to rely heavily on credit cards to earn the points I will need to travel.  The cards I am currently using include a legacy Chase Select Visa, United Club Card and my new all-time favorite, the Chase Sapphire Preferred card. There are also other specialty cards that I’ve found to be very useful for specific purposes. I’ll go into more details on the benefits of these cards and how I’m using them in future posts. However, the most important concept associated with using “credit card spend” to achieve your Pointing goals is this: NEVER carry a balance and ALWAYS pay your bills off in full every month!

What kind of Pointer am I?

Well from my answers to these questions you can see that a Profile of me has emerged.  I’m a non-Road Warrior who will be responsible for funding my own travel.  I’ll rely primarily on loyalty points earned from credit card spending. Since I live in Chicago, as a matter of personal preference I will by relying heavily on United Airlines.  These characteristics are going to influence the subject matter that I will cover in this blog.  In addition, I’m all about the “aspirational” trip.  However, getting there I realize will involve spending alot of time at the back of the plane. That said, I’ll also share with you how I’ve managed to take a bit of the sting out of “non-elite” travel.

The wealth of information available is simply staggering. I’ll take the approach of relaying to you what I’ve learned as it applies to my own situation.  I plan to personalize the whole Pointing process and give you concrete examples.  In some cases, I’ve not done things in the most efficient way and I’ll be ready to share those examples with you so that you can learn from my mistakes. I’m hoping to make Pointing a much more accessible and understandable endeavor.  This blog will likely be best suited to the budding Pointer who is trying to sift through a lot of information and is trying to make sense of it all.

I won’t try to be all things to all people.  In addition, there will be times where you will be learning things right alongside me. However, I feel I’ve learned a lot over the last several years and would be happy to share it with all of you as I do.

Oh yes, I guess I should also add a #9 to the definitions that started out this post:

9) Pointing / Pointer – a quick shorthand and misuse of the English language that will enable me to more quickly and concisely express the process of collecting and redeeming loyalty award points.  I’m not trying to be clever.  I’m just too lazy use a thesaurus for coming up with new ways to express this same concept.

With that, let’s get this blog started … and please, be gentle with me …

Turkey Day in Turkey?

For some people, part of the Thanksgiving ritual is to wake up early, strap on the running shoes and take a quick “Turkey Trot” to help counter the effects of an anticipated day of consuming copious amounts of turkey, stuffing and pumpkin pie.  For others, a leisurely walk around the block following the meal will do the trick.  However, for a travel and points obsessed person like me, the following idea popped into my head this morning … “Wouldn’t it be cool to fly to Turkey on Turkey Day? Why don’t I do a Mileage Run?”

Hmmm.  Let’s see, I could sit down to Thanksgiving lunch, go back for seconds and still have time for a tryptophan induced nap.  I then grab a carry on bag and head out O’hare and catch the following flight:

Wow, only $660 that’s a pretty incredible price. Very tempting!  Of course, I’m not quite sure if I’d be able to get buy in from my Partner F on this latest hair brained scheme of mine.  I’m sure I would get one of those “What are you nuts?” looks from him.

Perhaps a more plausible scenario would be to take a trip early next year.  For example, this is what pricing of flights from Chicago to Istanbul looks like in February:

Based on these rates, a flight to Turkey would cost LESS than the amount I am paying to visit my family in San Diego this Christmas.  In addition it is HALF the price of what we are paying to go on our upcoming trip to London.  I have my eye on the following itinerary:

Turkish Airlines is a member of the Star Alliance so we would be able to be able to collect 10,948 United MileagePlus points on this trip. In addition, the inbound and outbound flights are both non-stops which would save us a lot of time.  Furthermore, February 18 is Presidents’ Day which would make this a very viable “long weekend” option.

“Hey F, what do you think about spending Valentine’s Day in Turkey?”

(Insert, aforementioned “What are you nuts?” look here)

Happy Thanksgiving Everyone!

Where Points have taken me

I was very fortunate that my first job after graduate school was with an internationally oriented government agency.  That position enabled me to travel around the country and provided me with the experience of my first overseas business trip.  I next went to work for a European company.  That job also provided regular opportunities for domestic travel along with a 2-3 week annual temporary assignment to the company’s headquarters in London.  I started accumulating points and started to realize what points could do for me.  In 1995 I redeemed my first award.  What a concept … a “free” transatlantic plane ticket!

United Business Class Seat

However, when I went to work for a new company, my business travel patterns changed … and by changed, I mean that business travel for me effectively came to an end.  Don’t get me wrong, I loved my new job and career.  I find the work that I’m doing is intellectually challenging, I have great colleagues and I’m paid very well for what I do.  However, the tradeoff was that the nature of my role just doesn’t require me to travel for business. As a result, my primary source for generating points came to an end.

Pretty much all of my travel these days is purely for leisure purposes and I often “pay my own way” to get from Point A to Point B. However, I quickly discovered that there are other ways to accumulate points without actually travelling.  In fact, I earn more points now on an annual basis than I did when I was on the road for business.

I recently took an inventory of how I’ve used my points over the years and have come up with the following list (updated May 2015):

Year Award Destination
1995 1 Round Trip Economy Class Ticket on Northwest Airlines London, England
1998 1 Business Class Ticket on United Airlines Sydney, Australia
2000 3 Nights, Hilton Times Square New York, NY
2002 2 Business Class Tickets on United Airlines London, England
2005 2 First Class Tickets on United Airlines Sydney, Australia
2005 3 Nights, Hayman Island Resort Near Great Barrier Reef, Australia
2007 2 First Class Tickets on United Airlines Hong Kong and Thailand
2007 3 Nights, Royal Orchid Sheraton Bangkok, Thailand
2010 3 Nights, Sheraton Carlsbad Resort & Spa Carlsbad, California
2010 4 Nights, Hilton London -Tower Bridge London, England
2011 2 First Class Tickets on United Airlines Rome, Italy
2012 2 First / Business Class Tickets on American Airlines Buenos Aires, Argentina
2013 2 First Class Tickets on United Airlines Naples, Italy
2013 3 Nights, Hilton Sorrento Palace Sorrento, Italy
2013 2 Economy Class Tickets on Lufthansa Florence to London
2013 3 Nights, Andaz Liverpool Street London, England
2013 2 First Class Tickets on Lufthansa London to Chicago
2013 2 Business Class Tickets on United Airlines Amsterdam, Netherlands
2013 3 Nights, Doubletree Amsterdam Amsterdam, Netherlands
2014 2 Nights, Hyatt Regency Paris Etoile Paris, France
2014 2 Nights, Park Hyatt Paris Paris, France
2014 2 Business Class Tickets on Lufthansa Paris to Chicago
2014 2 First Class Tickets on United Airlines Chicago to Frankfurt
2014 2 First Class Tickets on Thai Airways Frankfurt to Bangkok
2014 2 Nights, Royal Orchid Sheraton Bangkok, Thailand
2015 5 Nights, Sheraton Krabi Beach Resort Krabi, Thailand
2015 3 Nights, Grand Hyatt Erawan Bangkok Hotel Bangkok, Thailand
2015 2 First Class Tickets, Cathay Pacific Bangkok to Chicago
2015 1 First Class Ticket, United Airlines Chicago to San Diego
2015 1 Economy Class Ticket, United Airlines San Diego to Chicago

The table above really demonstrates the concrete value of collecting points. As a Regular Guy in Chicago with a Day Job, I would never think of forking over $14,000 for a First Class Ticket to Bangkok.  However, by using points I was able to take just such a trip.

Thai Airways A380 First Class Seat Suite Frankfurt FRA to Bangkok BKK

How do I do it?  Well, I started this blog to share with others my experience in travel point collection.  Future posts will cover my personal tips, tricks and strategies.   I’ll also share with you what I’ve actually done with all of those points … though of course that will also entail subjecting the readers of this blog to my vacation photos.

I already have my sights set on a few Dream Destinations and the wheels are in motion for attaining those travel goals.  Naturally, I’ll be keeping you updated every step of the way.  However, as proud as I am of what I’ve been able to accomplish with points, thus far, there are some real Pros out there who have made the collection and redemption of points a true art form.

In particular, Lucky over at One Mile at a Time has served as the inspiration for my own blog.  Now that guy knows how to travel! I’m hoping that one day I’ll be able to look back on a Trip Index that will look like his .

I admit I’ve got a long way to go.  However, something tells me that I’ll enjoy the journey.  Stay tuned my friends.