Why you should always ask about upgrades

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Why you should always ask about upgrades

Some of the best travel deals I’ve ever negotiated have actually been at check-in. Often times if a hotel or car rental agency has better options available they will discount them when you check in. It’s why you should always ask about upgrades.

I ended up in one of the best suites in the world because I asked about an Upgrade: The Peninsula Suite Bangkok

Staying in one of the world’s finest suites wasn’t an accident – it happened because I asked if anything bigger was available. If you click the link above you can read more about the suite and the trip, but essentially we got an INSANE upgrade on our 3 night stay for about $500 each. Not cheap, I’ll admit, but it was a once in a lifetime experience.

Peninsula Bangkok- Peninsula Suite - 1 of 21

The suite was an entire floor – almost 4000 square feet.

Check the Inventory before you arrive

You need to know your information and your options. If you’re only staying for a night or two you’ll have better odds, but if you see some BALLER suite available for the time period you need – ask if they’ll sell it to you cheaper. If you see an incredible car that hasn’t been sold – ask if they’ll rent it cheaper. You’d be surprised how much you can get just by asking.

As an example here’s a look at the Ritz Carlton Kuala Lumpur in January 2017

You can see that the 2 bedroom suite is available. If it’s still available at check-in – ask if they’ll give you a great rate on an upgrade. In fact, I did this a few years ago and lemme tell you – it’s a phenomenal experience. Butler and all.


Leverage your status.

I just got a Mercedes C300 for a week and paid just $142 including taxes. I saw Sixt’s inventory before I got to the branch and saw they didn’t actually have any entry level cars even though they were renting them. I also saw they had quite a few swanky German offerings. I was then able to increase my odds by doing some research.  I read about a status match on One Mile At A Time and my Hilton Diamond status turned into Sixt Platinum which includes a 2 category upgrade. I’ll write more on this process, but the point is it doesn’t hurt to ask. screen-shot-2016-11-14-at-5-56-04-pm

If you have status with a brand…it will definitely help you

Last year when I stayed a night at the Grosvenor House in London, A JW Marriott hotel, I asked if any upgrades were available when I checked in.  Gold status isn’t the highest, but sure enough, the desk agent hooked me up with a One Bedroom Suite.

This brings me to my last point: BE NICE

Clearly Miles and I like to have fun. The more fun you are, nicer to be around, and ultimately gracious when talking with employees – the greater the odds they will hook you up. I couldn’t tell you how nice the dude was at Sixt and I WAS STOKED to cruise around in a new C300. Every suite I’ve gotten from a check-in bump I have let the staff know how much I appreciate it.

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The Chase Sapphire Preferred is a great starter card that earns Premium Ultimate Rewards that can be transferred into over a dozen partners many of which are US based. 

Welcome Offer

60k Points after $4k spend in 3 months

80k offer in branch currently – I think this should be online soon

Annual Fee


Points Earned

Transferrable Chase Ultimate Rewards

Super solid welcome offer.

If you carry this card alongside Chase’s cashback cards like the Chase Freedom Flex℠and Chase Freedom Unlimited® or the business versions: Ink Business Cash , Ink Business Unlimited you can combine the points into Preferred account and transfer into hotel and airline partners

Annual fee is quite low at $95 a year + you get a 10% anniversary bonus on points + $50 hotel credit in Chase travel.

  • 3x on dining
    •  including eligible delivery services for takeout
  • 3x on select streaming services
  • 3x on online grocery purchases
    • (excluding Target, Walmart and wholesale clubs)
  • 5x on all travel purchased through Chase Ultimate Rewards – Chase Travel Portal
  • $50 Annual Credit on hotel stays purchased via Ultimate Rewards/Chase Travel
    • The begins immediately for new cardmembers and after your account anniversary for existing cardmembers
  • 10% Anniversary Bonus
    • Every year you keep the card, your total spend will yield a 10% points bonus. If you spend $10k in a year, you’ll get 1k bonus points
  • Chase Sapphire Preferred® continues to redeem at 1.25c in the Chase Travel Portal and the slew of other benefits remain in tact including primary rental car insurance, purchase protections, etc.
  • Points are transferrable to 13 Ultimate Rewards partners
  • Redeem in the Chase Travel center for 1.25 cents per point
  • No foreign transaction fees
  • Suite of Travel and Purchase Coverage
    • Primary rental car coverage is my favorite

There is currently an 80k offer after $4k spend in 3 months available in branch, and up to 90k after $6k spend in 6 months. I suspect some version of this will be online soon if you don’t want the hassle of going into a branch.

We keep an up to date spreadsheet that lists the best ever offers: You can find that spreadsheet here.

Historically 60k is a very, very good offer. In 2021, we saw the offer hit an all time high of 100k. Who knows if that will ever come back. .

Main Cast: 

Cards that earn flexible points and should be used on the bulk of your purchases.

Supporting Cast:

Cards that earn fixed points in the currency of the airline/hotel and can not be transferred at attractive rates. These cards yield benefits that make it worth keeping, but not necessarily worth putting a lot of your everyday spend on. 

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