Ultimate Rewards: How to book with points despite online limitations


Ultimate Rewards: How to book with points

This is a story of courage and bravery, love and loss, tragedy and excitement…  Just kidding.  It’s not any of those things…  But it is a story about seemingly unattainable goals and persistence in the face of repeated obstacles.  Will the hero in this story win out?

Thanks to the 40K to Far Away Challenge the Frequent Miler team has been more motivated than ever to find great ways to eke out value from our points and cash.  This has led us to find things like the amazing 7.5K one-way award to Hawaii, how to find United 5K awards within the US, which Priority Pass lounges have showers, and much much more.  One discovery that I wrote about previously was the ability to use Chase points at 1.5 cents value with the Sapphire Reserve card to book cheap flights that don’t appear on the Chase travel portal (see: How to book the cheapest flights with Chase Ultimate Rewards).  The key, I thought at the time of writing that post, was simply to get transferred to the “help desk”.  But it turns out that there’s much more to the story…

A simple need

One of my 40K to Far Away plans involves arriving at a large international airport and picking up a one-way car rental to drive to my next adventure.  After a fair bit of research, I found only one major rental car company, Sixt, that offered pickup at that particular airport and drop-off where I needed to be next.  And, as luck would have it, the smallest Sixt car was quite cheap and there was no one-way drop off fee.  Awesome.

I could have booked this rental directly, but for one thing: most of my $400 budget for the 40K to Far Away Challenge was already spoken for.  I’ve used quite a bit for award fees, and I’ve reserved a fair bit for things like bus and subway transfers to and from airports.  Even now, I’m scraping the budget barrel for spare pennies.  For example, in one case I found a bus option that was $2 cheaper than the one I had previously planned, but it drops me off almost two miles from where I need to be.  Cool, I’ll take it.  A little walking is good for me, right?  I’ve never been this frugal before, but this challenge has me in serious cheapskate mode!

So, what was my alternative to booking the car directly?  I had just enough Chase points left over to pay for the majority of the rental at 1.5 cents per point value if I could book the rental through Chase.  I really wanted to do this because my alternative would be to cash out those remaining points at only 1 cent per point each.  With so few points remaining, we’re not talking big bucks here, but the little added value at 1.5 cents per point would make a difference in the challenge.  It could easily mean the difference between eating a complete meal or settling for yet another protein bar “meal” from my backpack.

It should have been simple.  I should have been able to log into the Chase portal, pick out the car, and pay for it with points.  But, of course, this wouldn’t be much of a story if it was simple.  Believe me, it was not.

Unable to find any cars

After logging into the Chase Ultimate Rewards portal, I selected Travel… Cars.  And to keep things initially simple, I plugged in a simple request to pickup the car at the airport and return it to the same place.  I figured that it would be good to see the round trip prices before putting in a one-way itinerary.

Unfortunately, even with this simple request at a major international airport, Chase was unable to find any cars.  It suggested adjusting my pick up to a nearby locations.  So, I tried again with the metropolitan area rather than the airport, but received the same message.  I wasn’t searching for cars in Dublin, but a Dublin search also returns zero cars, so this is a handy way to show you what the message looks like without revealing my real destination:

Well, poo.

I wasn’t done, though.  Not by a long shot.  I knew from past experience that it is sometimes possible to get Chase to book flight options not available online by calling and asking for the help desk.  So, I decided to try that approach for my car rental.  Little did I know that I was about to begin an epic quest for a tiny car rental…

Ultimate Rewards: How to book with points

Air, Hotel, and Car Team Agent 1: “Let me transfer you…”

After I described my plight, this agent quickly offered to transfer me to “someone who might be able to help.”  I didn’t have a chance to ask specifically for the help desk.

Air, Hotel, and Car Team Agent 2: “Can book special airfare, but not anything else”

I described the issue to this agent and she apologized.  She said that nothing could be done.  There was no way for them to book anything that wasn’t available online.  “But the help desk previously booked a flight option for me that wasn’t available online,” I said.  “Yes, we can make special airfare bookings, but nothing else.”  She was supremely confident about this statement and so I almost believed her.  In fact, I did believe her until I asked the next question…

Air, Hotel, and Car Team Agent 2 (continued): “There is no help desk”

Even though this agent almost completely convinced me that my quest was unobtainable, I wasn’t ready to give up.  So I asked her to transfer me to the help desk.  She replied that there was no help desk.  Um… what?  I explained that I previously spoke with someone at the help desk who told me that I could always call back and ask for the help desk.  She replied with something like “for travel requests other than cruises, we’re the only department.”

Okaaaay…  “Please transfer me to the cruise department,” I said.

Cruise Desk Agent: “I can escalate your case…”

The Cruise Desk agent was sympathetic, but unable to help.  She said that she couldn’t book cars without an accompanying flight or hotel booking.  Even then, she didn’t see any cars at the particular airport I needed.  I asked her about the help desk and she replied with something like “well, there is a department for escalating issues with existing reservations…  I suppose I could escalate your case…”  “Cool! Yes please!”

Help Desk / Escalations: “I can definitely help you with that today”

I finally made it to the help desk, or escalations desk, or something possibly useful!  After explaining the situation, the agent said “I can definitely help you with that today.”  What?  Wow!  I was happy dancing around the room!

She said that she had access to “the old system.”  And with the old system, she could indeed find cars at this particular airport.  And she even found cars from Sixt.  Unfortunately, she couldn’t find the drop-off location I needed.  This didn’t surprise me since even Kayak couldn’t find this drop off location.

I asked her if she could book directly through Sixt instead of through the system she was using.  “No, unfortunately, there’s no way we can book things outside of the system.”  Really?  Bummer.

I was about to let the whole thing go when I had an inspiration.  I asked her to book the car for pickup and return to the airport.  I would separately contact Sixt to see if I could change the drop off.  The agent agreed that this was worth a shot.  And she explained that there was no penalty for cancellations up until the time of the rental.  Cool.  We booked the round trip reservation with points.

Sixt: “unable to make any changes to reservations made by a third-party vendor”

Soon after booking the car from the airport where cars don’t exist on the Chase travel portal, I received the Chase confirmation email.  Almost a day later, I received one from RentalCars.com as well.  Apparently RentalCars.com is the company Chase uses behind the scenes for rental cars, at least when it comes to these “old system” reservations.

The RentalCars.com email led to a page to manage my reservation.  Not surprisingly, it wouldn’t let me change the drop-off destination.  That would have been too easy.  But it did give me the Sixt confirmation number, so I contacted Sixt to see if they could make the change for me.  Nope.  Here was their response:

We would be unable to make any changes to reservations made by a third-party vendor since changing the reservation in our system would effect the rate that you received with the third party.  However, you would be able to contact the third-party and make the requested changes through them directly.

RentalCars.com: “No changes to an affiliate booking”

Next, I called RentalCars.com to ask to change the drop-off.  The call center agent said that she would be able to do this for me but there was a prominent note in the file saying that no changes could be made to this affiliate booking.  I would have to go to the “affiliate” (which I assume is Chase Travel) to make any changes.  I asked her to look up my desired drop-off location to see if it would have been possible without that prominent note.  She found the desired drop-off and said yes.

Chase: “Happy to help. I’ll call Sixt”

Ultimate Rewards: How to book with points

When you call Chase about an existing travel reservation, I think you get connected with yet another department that is actually able to do things.  At least, that was my experience.  The call center agent listened to my request and immediately offered to call Sixt to get it done!  Holy helpfulness batman! Yay!

He warned me that I would be on hold for a long time (I was).  And yes, all told, it took about half an hour or more for him to make the change to my reservation, but he did it.  I don’t know exactly what went on behind the scenes, but one way or another the end result was that I had booked exactly what I needed.  Sweet!


Honestly I’m a bit mystified by Chase’s travel department.  Maybe I should say travel departments, with a long “ssss” at the end.  Officially, there are only two: the air, hotel and car desk, and the cruise desk.  Unofficially, I spoke with five people who all claimed to have different abilities to get things done.  Worse, most of them confidently asserted that what they could do was the absolute limit of possibility.  So, what should you do when you want to book something that isn’t available online?  Here’s what I suggest:

  1. Call and explain what you need.  When the first agent can’t help, ask for your case to be escalated.
  2. If you then get to the help department, they should be able to help you.  If they can’t fully help you, ask them to book something that’s close to what you want.
  3. Once you have a close to what you need booking, call to change it.  Hopefully you too will get the magic department with someone who can really help.

And, regarding 40K to Far Away… rental car success means that I’ll have a few extra bucks to buy a sandwich.  It was worth it.

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[…] Area Meetup: #40KFarAway Send Off (Oct 1, 8:30PM, near IAD) (9/28/2019) Ultimate Rewards: How to book with points despite online limitations (9/25/2019) Greg’s #40KFarAway practice: Driving Denali […]

[…] Ultimate Rewards: How to book with points despite online limitations […]

Peter Allemano

A very interesting read — and very entertaining too! Thanks for sharing your experience in such detail, Greag!


Head of Teavel at Chase should read this. Better yet Jamie Dimon should read it

Buffalo gal

I love this blog and find lots of helpful travel tricks here. Thanks Greg! I have an upcoming trip for a convention. Our organization has negotiated rates at several hotels in the city. Is there any way to book the hotel room through Chase so that I can pay with points at 1.5 cents per point?


What happens if you budget for a certain thing that suddenly becomes more expensive? For instance, what if your car company hits you up with a $200 drop charge at the end of the rental? Will you lose the competition? I always tell people that I travel with that the first rule of travel is that things go wrong. Given your extremely tight budget, I guess you don’t really have much leeway for contingencies.


Some of the comments here are weird. It is nice that some of the 40k to faraway has revealed some generally useful tips. But I think it’s equally clear that there are going to be things involved that none of us would ever do. Including, well, the whole concept.

If you’re not along tor the entertaining ride why bother to comment? This post itself states that Geg is walking two miles to save $2 so I think the gist of this thing is pretty well established.

Yes, I can confidently predict none of us is likely to make 2 hours of phone calls so we can save $8 and avoid eating hard candies stolen from an airport lounge as dinner. I think that is missing the point. I’m enjoying all of this.


wow, good finagleing, and patience with your quest


sounds like a lot of time wasted on the phone, for little gain…


I love this! And to RKToledo, the perspective is that now you don’t need a lot of time to make “all these calls” thanks to Greg’s article. 3 calls. And what other calls can you make in your daily life when you have a question about ANYTHING do not take time?

This sort of info is so helpful, you guys have saved me money and time and made me aware of possibilities many times. Thank you!


Many times I did similar trick, but not through Chase. For example, I book a car via OTA in a city, then when I pick up, I ask – can I return this car in the airport? They always said – yes. And vice versa – pickup at airport, dropoff in a city. Was never told no.


Might want to be careful with this one. There are plenty of cases where others are told the same (verbally) but get hit with a one-way after drop-off.


I’m still waiting for the “4 million to nearby” challenge. Based on the price of an economy ticket from Las Vegas to Cabo San Lucas on AA on Oct 2nd (over $2000 one way), I think I’ve already won. Just for kicks I priced a private jet and it was significantly more. FYI I broke down and bought a Southwest ticket–the last one offered.
I’d break out my pilot’s license and do the flight myself but I can’t find anyone willing to rent their plane for a flight into Mexico.


Some perspective is needed with this post. You have time to make all these calls because it is relevant to how you make a living. Everyone doesn’t have this kind of time and will stop after the first call. Good info to know though.


Precisely, and I would be one who gives up relatively quickly exactly because of the time involved, but the value of the 40k to Faraway to me is the process. In the end, I’ll vote for someone, but the appeal is really the things we learn along the way about a host of topics related to getting the most for our points and/or cash, some of which will make sense to my own bookings and some of which won’t.


Don’t jump to conclusions. Sure he said it was a cheap rental so the savings weren’t huge in this instance, but like everything in this game: THE TECHNIQUE is what’s important! Another time you could be in a position to save $1000 or more, then I bet an hour of calls would be much more acceptable.


Yes, chase uses Expedia as their travel portal and rentalcars.com belongs to expedia.