My two newest credit cards: both Southwest Airlines Visas!

If one of your New Year’s Resolutions is to travel more, then it’s time to jump into action and earn yourself one of the best travel-hacking values on the market: the Southwest Companion Pass.

I’ve written a lot about the Southwest Companion Pass in the past, but here’s what you need to know:

  • You earn it by accruing 110,000 Southwest miles in one calendar year
  • Once earned, it’s good for the remaining portion of that year and the entire next calendar year. Meaning, passes earned in early 2017 will be good all the way through December 2018.
  • The pass allows you to to get a FREE “companion ticket” for your designated companion ANY TIME the pass holder has a ticket on Southwest. It doesn’t matter if the main pass holder’s ticket was a paid ticket or free miles ticket. If they have a ticket, the companion gets a ticket, so long as there is still space available on the place REGARDLESS of the current price of those tickets.
  • Points earned from Southwest credit card bonuses DO COUNT towards the points threshold.

That last point is the most important one. Because right now, and for a limited time only, both Southwest credit cards, the Premier and the Plus Visas, are currently offering 50,000 mile bonuses for spending $2,000 in the first three months of card ownership. That’s 10,000 – 20,000 points higher EACH than the offers they run at other points in the year.

If you were to get both cards (as we’ve just done) and complete the minimum spending for each bonus, that already puts you at 104,000 miles earned towards the 110,000 needed to get the pass. You can then pretty easily earn those last 6,000 miles either by spending on the credit cards, flying paid flights on Southwest, or taking advantage of items like their shopping portal.

And the best part? If you earn the pass in this way, you still get to keep the 104,000 points you earned along the way. As such, many of those first few flights for the pass holder can be absolutely FREE too, just like their companion’s.

Now, time for my common caveats: if you don’t have good credit, this may not be an option for you, as it’ll be hard for you to get approved for both cards. If you don’t regularly and consistently pay off your full credit balance each billing period, you shouldn’t be messing around with high interest-rate cards like this in the first place. And finally, if you don’t normally spend at least $2,000 in credit cards over three months time, then I generally don’t think it’s a good idea to “manufacture” spending just to earn the credit card bonus.

Finally, in the past year, we’ve seen Chase (the card issuer) institute a new rule about travel bonus-earning credit cards; they’ll only allow you to open 5 maximum in any 24-month period. So if you’ve opened a lot of other cards recently, this may not be an option for you, either.

But, if you’ve got good credit and it’s just a matter of switching your current spending to a new card? Then this is a fantastic deal that lets you essentially travel the country for free for two full years with very minimal effort.

Happy flying!


4 Steps We Took to Save $700+ on Flights to Cancun

This week, after planning out our travel itinerary for all of 2017, it was time to turn to booking and making those vacations we’d planned out in a document actually come to life!

As I discussed in that last post, one of our strategies for elongating our vacations is to book over holiday weekends; unfortunately for cash-based rewards systems (in which the amount of points needed for an award is tied to the cash price of a ticket) holiday weekend are usually more expensive redemptions.

So, sometimes we have to get a little creative. We ended up booking 2 nonstop, round-trip flights from Austin to Cancun over President’s Day weekend on Southwest. The retail price of this trip was $1,012 at time of booking. But we managed to book those same tickets and only spent $276 — just about a quarter of the price.

How’d we do it?

Well, this one took a few steps. At time of booking, the hubby had around 17k Southwest points in his account leftover from work travel this year. I had around 9k in my account. And perhaps most importantly, the hubby had just received 2 $100 “Luv Vouchers” from Southwest for a severely delayed flight experience a few weeks earlier.

Step 1: I booked the most expensive single leg using the hubby’s points stash

This was fairly straightforward. The most expensive leg of this trip was the return flight to Austin at 13,912 Rapid Rewards points. So I booked that with the hubby’s surplus of points, but I booked it in my name – not his. (Reason for that coming later.)

The important thing about this step is the ORDER that I did this. Knowing that I’d be using points for my flights, I needed to book my flights BEFORE I booked the hubby’s paid flights. Because Southwest ties their awards to the cash value of the ticket, and the ticket price is tied to the remaining availability on the flight, I may have risked increasing the points-price of the ticket had I booked the hubby’s paid ticket first.

And, indeed, after booking both his and my ticket, the points price of that return leg has now risen to 17,708 points. So knowing the right order to book in saved me nearly 4k points.

Step 2: I transferred the hubby’s Chase points to my Chase account

With step one complete, my return flight was booked, so I now needed to book my departing flight. Unfortunately, I didn’t have enough Southwest points to book the 13,912 point award flight with the points left in my points stash. (And Southwest doesn’t offer a free points transfer for spouses; you *can* transfer points to other people, but they charge you a hefty fee to do so.)

However, we did still have some Chase Sapphire Reserve points left, and Chase points transfer at a 1:1 rate to Southwest Rapid Rewards. Unfortunately, that card is also in the hubby’s name, and Chase only lets you transfer points to accounts affiliated with the user OR authorized users of the account. Since it costs an extra $75 to become an authorized user, and doesn’t garner you any extra benefits, I wasn’t one.

But, there’s a workaround. Since I also have a card with Chase Ultimate Reward benefits, the hubby was able to do an immediate transfer of points to my Chase account. And then, of course, I could transfer those points to my own Southwest account.

Sunset in Cancun by Flickr user Jose Luis Cruz under a Creative Commons license.

Step 3: I transferred Chase points to Southwest to book my departing leg

So, with an extra 4,000 points recently transferred over to my Chase account, I was able to transfer those at a 1:1 rate to my Southwest account.

Combined with the points I already had in my Southwest account from recent work travel, that was enough to cover the cost of an award flight on the way to Cancun, at 13,912 points. And voila, suddenly I’m going to Cancun, baby.

Step 4: I booked the hubby’s travel with cash + travel vouchers

Now, with my travel secure, I went back to the hubby’s account.  The hubby had recently received two $100 Southwest Luv Vouchers, as an apology for a very bad flight experience on a work trip where he was about 6 hours delayed. So our goal was going to be to use those vouchers on his flights for two key reasons:

  1. Southwest Luv Vouchers expire, so it’s use ’em or lose em.
  2. Southwest Luv Vouchers can ONLY be used for tickets in the name of the passenger to which the voucher was issued.

That second reason is why we used points for my ticket, but cash for the hubby’s, even though moving the points around was a little more labor-intensive. Applying the Luv vouchers, that took the price of the hubby’s RT tickets down to $261.

So there you have it. For longtime readers of the blog, though, you may be asking “but why didn’t you just use your Southwest Companion Pass for the second ticket?” Well, the reason is that our pass is expiring at the end of this year. We’re going to work towards earning it again, but it’s not certain that we’ll have the 2017-2018 pass in time for this trip.

If we DO earn the pass, though, that’s yet another reason that I bought MY fare on points — that would allow me to keep my mostly free fares and still let us CANCEL the hubby’s cash ticket and rebook it for free with the companion pass. Meaning our ending out-of-pocket costs for these flights could end up being even lower, like around the $100 mark for just taxes and fees only!

In the end, all these steps did take me at least a solid hour to complete, and of course, I had to know about all these points and miles rules as well. But if an hour of work can save me $700? Yeah, I’m into that! Here we come, Cancun!

Header photo courtesy of Oasis Resorts in Cancun.

How We’re Saving $1,200 on our Five-Star Dublin Hotel

If you’re a fan of the blog, then you’ve likely been following our planning for next year’s UK & Ireland trip, including how we saved $6,500+ on our business class flights using Citi & Chase points on Singapore Airlines, and how we saved ~$600 on our hotels in Manchester & Liverpool using Starwood points.

The next item up for us to book was going to be the hotel for the bulk of our stay, in Dublin. The hubby wanted to stay right in the heart of the city centre, where (in his own words) “we could try a new pub every night and eat all the things.” And I mean..who could argue with that logic?

As we’d recently earned 100,000 new Chase Ultimate Rewards points for meeting the minimum spending requirements for the Chase Sapphire Reserve card, we were happily sitting atop roughly 114k UR points, and given the improved redemption rate for Chase Sapphire Reserve cardholders, we knew we could turn those points into $1,700+ of free travel through the Chase travel portal.

The only real question was whether that would be the best use of our points. In the past, we’ve frequently transferred UR points over to Hyatt, because of the great value of the Hyatt loyalty program. Unfortunately, Hyatt doesn’t have any hotels in Dublin, and so this time that wasn’t an option.

Another option was paying outright with our Citi ThankYou Prestige card, and using the 4th-night free benefit to get a reimbursement for the cost of the 4th night. However, with this method you don’t get the reimbursement until after you complete your stay, and we’re not sure right now whether it’s worth it to keep our Citi card for another year, given the steep $450 annual fee.

So that had us back to booking via the Chase Ultimate Rewards portal. From here, I just needed to research what hotel was best for us. After looking at reviews on Yelp, TripAdvisor, and several other sites, I had narrowed it down to either The Morgan or The Fitzwilliam. Both hotels were five-star properties with overwhelmingly positive reviews, but a slightly lower price and the fact that it’s allegedly Beyonce-approved pushed us towards ultimately deciding on the Fitzwilliam.

One thing I really like about booking through the Chase portal is that, unlike is often the case with award nights booked directly with the hotel chains, you can usually book any available room through the portal and not just the lowest-category room.

The lowest tier room at the Fitzwilliam.

As such, we reviewed the Fitzwilliam’s offerings and opted to upgrade from the “Executive Double” room to the “Signature Room” for just 3,000 additional points total; I mean, after all, it is our vacation — worth a little splurge. And in my experience, you’re also much more likely to be upgraded from a higher starting point room than if you book the bottom of the barrel.

Yet for just 3,000 more points, we could upgrade two full categories!

Taking a look at this room category through the hotel’s website, we would have had to pay €1146, or roughly 1,257 USD across our entire stay.  But using the Chase portal, we were able to secure our stay for four nights in a Signature room for just 80,910 UR points. That’s even slightly better than the stated redemption rate of 1.5 cents per point; closer to 1.6 in fact.

If you’re keeping track, that means that the total value of our trip to date is $9,598.44, and we’ve only had to pay $941 of that ourselves, meaning 91% of this trip so far is ABSOLUTELY FREE to us. 

Next step: positioning flights, trains, and ferries to get us from city to city along the way!

Header image courtesy of The Fitzwilliam Hotel Dublin, a member of the Preferred Hotels and Resorts group.

How the SPG & Marriott Merger Can Help You Get More Free Hotel Stays

As of this past week, SPG (the parent chain behind such hotels as W, Westin, Sheraton, and many others) is officially part of the Marriott company.

While many, myself included, predicted a bit of gloom and doom* about this merger, for now at least, the brands are playing nice. It was announced that Starwood points would transfer at a 3:1 rate to Marriott points, and that loyalty status holders would get an instant status-match between the two brands, as well as the Marriott-owned Ritz Carlton program.

Generally speaking, this is good news for Starwood loyalists who had come to enjoy one of the most rewarding loyalty programs in the game. And it’s also good news for us, former Starwood loyalists, in regards to our upcoming UK & Ireland trip.

Albert Square Plaza in Manchester, photo courtesy of Marriott

The primary cities we’re planning on exploring during our 9-day trip will be Liverpool, Dublin and Manchester. Starwood has hotels in 2 of these cities (Liverpool and Dublin) but not in Manchester. Meanwhile, Marriott has no hotels in Dublin, but has multiple options in Liverpool and Manchester.

Looking at our respective points balances (we had a measly 1,315 Marriott points, but a respectable 40,096 SPG points), we saw that we could easily book our hotels for both the Liverpool and Manchester parts of the trip with just our existing bank of points, thanks to the recent merger.

First, we booked two nights at the Aloft Liverpool, a modern hotel in a gorgeous old building (see header photo) for a mere 3,500 points per night (btw, Aloft is an SPG brand, which is why this is a very acceptable redemption rate!)


This left us with around 33k SPG points, so then I turned to the Marriott site, to find a high-ranked property in the downtown area of Manchester. And lucky for us, the Renaissance Manchester City Centre Hotel had availability for 60,000 Marriott points, which at 3:1 rate, translated into just 20,000 SPG points for a two-night stay. We instantly transferred the 20k points over, and booked our room.

So, that means we’ve now booked 1/2 of the hotel nights needed for our trip with just our current surplus of Starwood points — no new credit cards or spending schemes required — and still have around 13k points leftover. This translates into a savings of $688, making the hotel rooms for this section of our trip entirely free.

We’ll likely book the rest of our trip using the points we’ll gain from our brand new Chase Sapphire Reserve card to book the Dublin portion of the trip, and will only have to spend out-of-pocket for taxes, meals and ground transportation.

(*That all being said, Marriott is still terrible. I called them today, asking if they were doing any sort of status match for existing Hyatt Diamond members — the highest level of Hyatt loyalty — and got an entirely rude and unhelpful response. Our plan is to use up these last few SPG/Marriott points, and then avoid the chain entirely in the future.)

Header image courtesy of SPG.

How We’re Saving $6,500+ on a Trip to the UK and Ireland

Well, we finally did it.  After a little bit of heartbreak, and a little bit of confusion, we finally booked a trip for early next year with all those points we’d transferred over to Singapore Airlines a couple months back.

To recap: after earning more than 200,000 points across our Chase Ultimate Rewards and Citi ThankYou Rewards accounts, largely thanks in part to credit card bonuses and strategic bonus-category spending, we’d earned enough transferrable points to book a first class trip on Singapore Airlines Houston – Moscow route. Unfortunately, just as we were ready to book, Singapore Airlines discontinued the route, leaving us scrambling to find an alternative destination for a similar amount of points.

In the end, we’ve booked a trip to Manchester, England, which will be our jumping off point for a trip across central England and Ireland. We’ve had to settle for business class instead of First (at least, for now) but Singapore’s business class still comes with lie-flat seats, their famous “Book the Cook” feature, and all the champagne we can drink both pre- and mid-flight.

So what will this fancy trip set us back, you might ask? If we’d been paying out of pocket, quite a bit:


But luckily, thanks to our points, we ONLY paid the taxes and fees – in other words, the two of us will get a full trip to Europe, in business class on the world’s top-rated airline, for only about $1,200.

We didn’t stop there, though. We put the taxes & fees on our brand new Chase Sapphire Reserve card, which gives us a $300 statement credit each year for travel-related purchases. So the total cost of the flights out of pocket was just $941, or ~$235 per person, per flight. That’s less than many domestic economy flights!

Putting the purchase on that card will also help us earn more points — namely  the 100,000 Chase Ultimate Rewards we can use towards hotels, positioning flights or activities, by meeting our spending requirement for the bonus offer on that card. And since this was a travel purchase, we’ll earn 3 points per dollar on the spend, or an additional 3,600 UR points, worth roughly $54 in future trips, as well.

As we continue planning, I’ll post about how we’re also saving money on our positioning flights, hotels, and activities as well, so stay tuned. And in the meantime, if you have any recommendations, especially in Manchester, Liverpool or Dublin, let us know in the comments!

Header image by Flickr user autumnal_fires under a Creative Commons license. Image has been cropped.

Introducing the Chase Sapphire Reserve Card!

We just got a new credit card! It’s always exciting in the miles and points game when you’re approved for a new card and can start dreaming about all the benefits that go along with it.

Today, it was the Chase Sapphire Reserve card. The card comes with a $450 annual fee, which is quite hefty, but look at all you get:

  • 100,000 Chase Ultimate Reward points for spending $4,000 on the card in the first three months of card ownership. This benefit is made even more attractive by the fact that cardholders will receive a value of 1.5 cents per point in the Ultimate Reward travel portal (as opposed to 1 cents for most Chase cards, or 1.25 cents for the Chase Sapphire Preferred), making this benefit worth AT LEAST $1,500 in travel benefits.  Of course, through transferring to travel partners, you can get even more value here.
  • $300 statement credit for travel expenses per calendar year.  Yes, calendar year, not cardholder year. Meaning you can get it now, and then again in January, without needing to pay another annual fee.
  • $100 statement credit for Global Entry. We already have Global Entry, but it makes a great gift, meaning we can save $100 from our Christmas budget
  • Priority Pass lounge access.  This was pretty much the only remaining useful benefit on the Citi Prestige card, which we’ll be cancelling as soon as we close out this whole Singapore Airlines booking debacle. But now we’ll still have that access as well. I value this at around $60 a year in value for us.
  • Lots of other consumer & travel protection benefits and concierge type services.

So, we’re going to pay $450 for this card, and get a minimum of $2,260 in value.  This is why we travel hack!

One worthwhile side note though – this card, like all Chase and Citi cards – is governed by the 5/24 rule.  This rule states that they’ll only approve you for a new card if you have less than 5 cards opened in any 24 month period with that bank. So if you’re already pretty heavy into travel hacking…this may not be an option for you.

For anyone just starting out though, these are pretty amazing benefits. Just remember to cancel the card before your 1-year mark, or be prepared to pay the $450 annual fee once again. Happy travels!

The Singapore Airlines Booking Saga Continues…

About a month ago, I posted about how after transferring all the points we’d saved over a 2-year period over to Singapore Airlines, they did away with the route that we were planning on booking.

Since then, I looked up EVERY single route that Singapore Airlines flies out of the US for the March – June 2017 time frame.  After considering our options, it seemed like the newly announced IAH – MAN flights that replaced our original route (IAH – DAM) were probably going to be our best option.

Only one issue: Singapore Airlines doesn’t seem aware this route even exists. You know you’re not going to have good booking luck when you’re having to educate customer service about their own press releases…


Le sigh. Still no trip planned for us.

How a Quick Phone Call Earned Me 12,000 Points

We’re currently deciding where to go with our Citi points. One option: Stockholm!

Around this time last year, I talked about how we’d just started a new round of card churning with the Citi Prestige and Citi Premier cards.

It was a good combo – we earned 100,000 Citi ThankYou Points between the card bonuses, as well as a lot of extra perks from the Prestige card alone.  To date, we’ve received:

  • $500 in air travel credits ($250 reimbursement per calendar year)
  • a $90 statement credit for Global Entry
  • Admirals Club access for me while on a work trip ($30 value in the wine I drank alone)
  • Priority Pass lounge access for the hubby and I on our lackluster Sandals trip (an $80 value in food, drinks and internet).

So, despite the fact that we paid a $450 annual fee for the Prestige card, we essentially got $700 of value, before even taking into account the bonus points — in other words, we MADE $250 by getting this card. And by Citi’s own calculations, the bonus points we got between the two cards are worth somewhere between $1,000 – $1,600 in travel.

However, the Prestige card is up for renewal next month and the hefty fee did cause us to take pause; it didn’t seem worth it to keep it for another year. But since I’d set a reminder on my calendar to call in advance of the fee being assessed, I had a little bit of leverage.

So, I called Citi to see what could be done.  If I cancelled the card outright, I’d lose all the points I’d earned from the account within 60 days.  Since we’re not quite ready to book a trip with all these points, that wasn’t a good option.  I was hoping they would agree to waive the fee entirely, but it appears that wasn’t an option either.  However, I was able to negotiate an additional 4 points per dollar spent on restaurants for the next six months, up to a 50,000 point limit, if I agreed to keep the card.

Considering that we have several trips coming up these next few months, I think we could easily expect the additional bonus from this promotion to be worth 10,000 – 15,000 additional points (so between $100 – $240 in value).  When combined with the additional $250 in airline reimbursement we’ll get in 2017, and the ability to hit up a couple more lounges on trips through the next year, the card will once again pay for itself, and it buys us another year to figure out what to do with our points hoard.

Making that phone call isn’t specific to Citi, either. Whenever I open a new travel credit card, I immediately add on my calendar a reminder one-month before the card anniversary. Then, I can call and negotiate, or if necessary, cancel. It’s just a fundamental step of the travel hacking game that a lot of people forget.  But considering how productive it can be, it’s definitely worth it!

Header photo courtesy of Flickr user Olof Senestam under a creative commons license. 

Trip Report: Weekend in San Antonio, Part One – the Hyatt Regency

As I wrote about a couple months back, getting loyalty status with various travel brands can certainly make frequent travel a lot easier. Sometimes, it also makes it a lot more luxurious!

Seeing as how I recently acquired Hyatt Diamond status for free, I figured it was high-time to take advantage of it. And since our anniversary was also coming up, I decided to see if I could book a nice room on the Riverwalk for little-to-no out of pocket cost using my points + status for our anniversary weekend.

There are two Hyatt properties right on the riverwalk in San Antonio – the Hyatt Regency San Antonio (which is older, but in a prime location) and the Grand Hyatt San Antonio (which is huge and new, but in a quieter section of the Riverwalk). Standard room rates for both properties during the timeframe we were looking started around $229 a night, which was a little steep for a last-minute getaway.

We looked at doing a pure points booking, but at 12,000 points per night, that only came out to a redemption rate of 1.9 cents per point. Given that we’d be transferring points over from Chase Ultimate Rewards into my Hyatt account, that’s not a very effective redemption rate. (Chase Ultimate Reward points are roughly valued at about 2.1 cents per point at present; trading in points for a lower redemption rate is considered a poor use of points.)

So, things weren’t looking great – until, that is, we looked at the points + cash rates. 

One of the properties, the Hyatt Regency San Antonio Riverwalk, was offering a points + cash rate of 6,000 Hyatt points + $75 a night for the dates we wanted. That meant the points portion of the stay would jump up to a 2.6 cents per point redemption rate – a pretty nice value for the Chase points we’d earned with our Chase Sapphire Visa.

However, my Hyatt Diamond status also comes with four “Suite Upgrade” certificates each year, delivered around the first of March. Each certificate is good for upgrading any regular room booking to a suite for up to a seven-night stay at any Hyatt property, and can usually be confirmed at time of booking. The certificates are only valid on paid stays, but lucky for us, points + cash rates count as a paid booking for suite certificate purposes!

Combining the cash + points rate with a suite certificate, we were able to secure what we thought would be a “Regency Suite,” as that’s listed as the lowest level suite for the hotel on the Hyatt website. Hyatt doesn’t advertise the rates for suites at this property, but compared to other comparable Hyatt properties, it probably averages about $400-$500 a night for a cash booking.

Unfortunately, when we showed up, we weren’t placed in a Regency Suite, but in an “Atrium Suite”.  Fair warning – these may be considered “suites” because they have a separate bedroom and living area but they’re AWFUL. Seriously.  You’re better off in just a standard room, as these have no windows, zero natural light, the world’s worst balcony…just…yuck.

The living room area of the Atrium Suite was cramped and dark.
The small, windowless bedroom of the Atrium Suite
The craptastic balconies of the Atrium Suite. They’re not even big enough to put a chair on and overlook the conference center instead of the outside.

Not wanting to ruin our anniversary weekend in such a horrible room, we returned promptly to the front desk and asked if they had anything else.  They said their suites were sold out, so they offered us an “Executive King with Partial River View.”  Disappointed, we took the offer and went to check out room #2.

Our second room was definitely an improvement over the Atrium Suite (if you’re listening, Hyatt, you should seriously get rid of those rooms altogether…) but wasn’t what we were expecting either.  It was a small room with no couch, only one chair (with a mismatched ottoman) and a small desk. Overall, still quite a disappointment from what we thought we had reserved.


The Executive King Room was small – built for one person, not two – but at least it had  nice floor to ceiling windows.

So, we took to social media, and messaged the Hyatt Facebook account. Hyatt is pretty legendary for their customer service, and has even won awards within the social media industry for their world-class social customer care programs. And they did not disappoint. Within 2 minutes of sending my first message, they had responded to request additional information, and within 30 minutes, had managed to reach out to the hotel manager to make things right.

When we returned down to the hotel lobby for the second time, the manager greeted us by name and apologized for the mix up, then offered us a “Riverbend Suite” — the nicest suite they have at this property, with a separate bedroom, two bathrooms (!!!), and a fantastic river view.

The view from our Riverbend Suite, where we could see revelers on the Riverwalk below and horse-drawn carriages on the streets above.
The living area in the Riverbend Suite was spacious, bright and airy.
The bedroom in the Riverbend Suite was a great size, and very inviting.
The bathrooms in the Riverbend Suite were pretty standard EXCEPT that we each got our own, which was amazing.

Third time was indeed a charm, and our final room was FANTASTIC. In fact, we liked it so much, we immediately called room service and asked them to send up a bottle of champagne so that we could toast the start of the weekend and do a little people watching of those down below on the Riverwalk.

All in all, we ended up spending just $150 out of pocket (plus taxes) for two nights in the Hyatt’s top level suite, which would have surely cost well over $1,000 if we’d booked the same with cash.  For the points-aholics out there, it was essentially like getting a 7 cents per point redemption value.  That’s a points + status win if I’ve ever heard one. 🙂

Tomorrow, I’ll bring you part two, and detail all the things we saw and (more importantly) ate in San Antonio, so stay tuned!

The Cash + Points Booking Trick You Need To Know About

The lobby of the Hyatt Regency Minneapolis. (Photo courtesy

The hubby is away this week at a work conference in Minneapolis, a city that neither of us had previously ever been to. And while his work was picking up the tab for his hotel room starting this past Saturday, I suggested we tack on a night to the front end of his trip so that we could explore the city together beforehand, and then I could fly home once the conference started.

I used my Southwest companion pass to fly up to Minneapolis with the hubby for free, then booked my return ticket using my own Southwest points, making my flights gratis.  Then, we added a free night using Hyatt points (actually Chase Ultimate points that we had transferred over to Hyatt) in the same hotel that the hubby’s conference was in, the Hyatt Regency Minneapolis.

But here, I used a trick of the trade that will often help you to upgrade a longer stay for cheap: I booked the points portion of the stay in a higher category room than the hubby was booked in for the conference.  In this case, I paid 17,000 Hyatt points to get us a room on the Club level – which includes free breakfast, evening hors d’oeuvres, free bottled water and sodas, and an upgraded room itself – instead of the 12,000 points it would have cost me to just book a standard room.

And here’s why: most hotels, if they have the space available, will attempt to let guests on back-to-back bookings stay in the same room for their entire stay. 

My breakfast from the Club lounge.  Offerings included a wide variety of cereals, yogurts, and pastries, fruit, hard boiled eggs, smoked salmon, bagels, and fresh juices.
My breakfast from the Club lounge. Offerings included a wide variety of cereals, yogurts, and pastries, fruit, hard boiled eggs, smoked salmon, bagels, and fresh juices.

So even though only the one night points-portion of my hubby’s hotel stay was “supposed” to be on the Club level, the hotel was able to give him a Club-level room he could keep even through the cash-portion of his stay (which should have been a standard room at the “conference rate” that his work paid.)

As such, if you give a conservative estimate that the perks of the Club level are worth about $30 a day (in savings from not having to buy breakfast, bottled water, snacks, etc.), then the extra 5,000 points that we paid to get on the Club level for the extra night ended up being worth $210 over the course of his entire weeklong stay. In redemption terms, that comes out to roughly 4.2 cents per point value – which is nearly 2.5 times the current estimated value of Hyatt points, or double the estimated value of Chase Ultimate points.

Now let me be clear – the hotel was in no way required to do this. They could have just as easily made us switch rooms after our points stay to a standard room, and they would have been totally in the right to do so. And if they had made us change rooms, the redemption value on those extra 5,000 points would only be 0.6 cents per points for one day’s worth of Club access- pretty measly.

Still, I’ve found this trick works well over 1/2 the time – making it a gamble I was willing to take.  It’s also good to remember that you could do this the other way around just as easily, with an upgraded cash portion of your stay at the front of the trip, followed by standard-room level points redemption at the back end.  Whichever way you book it, just make sure the higher-level room is at the beginning of your stay, and don’t be upset with the check-in agent if it doesn’t work out.

Tomorrow, I’ll detail where we went and what we saw in the great city of Minneapolis, so stay tuned!