We may receive a commission when you use our links. Monkey Miles is part of an affiliate sales network and receives compensation for sending traffic to partner sites, such as CreditCards.com and CardRatings. This relationship may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. Monkey Miles is also a Senior Advisor to Bilt Rewards. Terms apply to American Express benefits and offers. Enrollment may be required for select American Express benefits and offers. Visit americanexpress.com to learn more Opinions, reviews, analyses & recommendations are the author’s alone, and have not been reviewed, endorsed or approved by any of these entities.
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.
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. 
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.
Opinions, reviews, analyses & recommendations are the author’s alone, and have not been reviewed, endorsed or approved by any of these entities.
Chase Sapphire Preferred® Card
Welcome Offer
Earn 60,000 bonus points after you spend $4,000 on purchases in the first 3 months from account opening.
Annual Fee
$95
Points Earned
Transferrable Chase Ultimate Rewards
- 5x on all travel purchased through Chase Travel℠
- 3x on dining, including eligible delivery services for takeout & dining out
- 3x on select streaming services
- 3x on online grocery purchases
- (excluding Target, Walmart and wholesale clubs)
- $50 Annual Chase Travel Hotel Credit via Chase Travel℠
- The begins immediately for new cardmembers and after your account anniversary for existing cardmembers
- 2x on all other travel
- 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℠ and the slew of other benefits remain in tact including Auto Rental Collision Damage Waiver ( primary ), purchase protections, etc.
- Points are transferrable to 14 Ultimate Rewards partners
- Redeem in Chase Travel℠ for 1.25 cents per point
- No foreign transaction fees
- Suite of Travel and Purchase Coverage
- Auto Rental Collision Damage Waiver is my favorite
- Get complimentary access to DashPass which unlocks $0 delivery fees and lower service fees for a minimum of one year when you activate by December 31, 2027.
- $95 Annual Fee
We keep an up to date spreadsheet that lists the best ever offers: You can find that spreadsheet here.
Historically 80k is a very, very good offer and hit in both 2022 and 2023. 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.
The Chase Sapphire Preferred® is exceptional starter card and offers transferrable Ultimate Rewards, and pairs well with other Chase cards.
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.
The responses below are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved, or otherwise endorsed by the bank advertiser. It is not the bank advertiser's responsibility to ensure all posts and/or questions are answered.