Haven’t Made Your First Miles & Points Redemption Yet?  Then This Is the Post for You!

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If you’re sitting on a pile of Chase Ultimate Rewards points but haven’t been able to decide how to use them, then this post is for you.

A few weeks ago I got a message from a friend, Josh, that said he was coming to Chicago to play in the Ultimate Frisbee US National Tournament.  And he was planning on using the bonus he earned on his new Chase Sapphire Preferred Card to cover the airfare.

This was Josh’s first time redeeming miles or points for travel.  So I’ll share how we went about booking the trip.  And show you how to quickly and easily decide on the best way for you to use Chase Ultimate Rewards points to get Big Travel with Small Money.

Josh started off looking for flights on the Chase Travel Portal.  The options he found that fit his schedule would have set him back over 47,000 Chase Ultimate Rewards points just for his flight!

But using a little transferable points magic he ended up booking his flight and 3 nights in a hotel for half the points he was originally planning to pay just for the airfare!  If that sounds confusing, don’t worry!  I’ll show you how to get value from your Chase Ultimate Rewards points without being an expert.

You Can’t Go Wrong If You’re Getting the Trip You Want

If you’re overwhelmed trying figure out the most efficient or cost effective way of booking travel with miles & points then remember this quote:

If it’s worth doing, it’s worth doing poorly

I’ve made plenty of miles & points “mistakes.”  I’ve used an absurd number of points to book dingy hotels, I’ve booked over-priced award flights, and I even shelled out $500+ in fees for a coach award flight (I’m shaking my fist at you London!).

Those were all part of my education and it was still way cheaper than college!

Redeeming miles & points for a “poor” value is better than not redeeming them at all!  And I would argue that all those “mistakes” were actually the best redemptions I’ve made because it got me interested in Big Travel with Small Money.  And it’s led to a lot of wonderful experiences I wouldn’t have had otherwise.

Understand What Your Points Can Do and Save Time & Money!

Because the Chase Sapphire Preferred is such a great card for beginners (and it’s the card Josh has), I’ll show you how you can easily use your Chase Ultimate Rewards points to save on travel expenses.

If you’re looking to get into the miles & points hobby, you can’t go wrong getting the Chase Sapphire Preferred card.  With it you can earn a 50,000 Chase Ultimate Rewards point bonus after spending $4,000 on purchases in the first 3 months from account opening.  And as you’ll see, this is a valuable bonus.

If you have the Chase Sapphire Preferred, there are 3 ways you can redeem your Chase Ultimate Rewards points for travel:

• Cash back
• Book travel through the Chase Travel Portal
• Transfer them to Chase’s travel partners

That’s it!  You can take a deep breath now because you only have 3 choices!  And if you have a rough idea of your travel plans, you should quickly be able to narrow down your choice.

Let’s look at the basic advantages and drawbacks of each method.

Cash Back

This is the quickest and easiest method because all Chase Ultimate Rewards points are worth 1 cent each as cash back.  So 50,000 Chase Ultimate Rewards points are worth $500!  Don’t ponder, don’t plan, just get the cash.

Think about this for a second.  If you get the Chase Sapphire Preferred card, the $95 annual fee is waived the first year.  So if everything falls apart – your passport is revoked, you’re put on the no-fly list, the sky falls down – you can still walk away with $500 in your pocket.

Chase Travel Portal

You can pay for travel booked through the Chase Travel Portal with your Chase Ultimate Rewards points.  The value of your points varies between 1 to 1.5 cents each, depending on which Chase Ultimate Rewards card you have.  This is an easy way to get more value for your points.

And it doesn’t take much extra time because you won’t have to worry about blackout dates or jump through the hoops airlines and hotels have if you want to book awards with them.  And you’ll still earn frequent flyer miles on your free flights with this method!

You can book flights, hotels, rental cars, and a variety of activities (including cruises!) this way.  If you want to know more about this option, read our detailed step-by-step guide on booking with the Chase Travel Portal.

With the Chase Sapphire Preferred card your Chase Ultimate Rewards points are worth 1.25 cents each toward travel booked through the Chase portal.  So 50,000 Chase Ultimate Rewards points are worth $625 in travel (50,000 Chase Ultimate Rewards points X 1.25 cents each)!

Transferring to Travel Partners

This can be the most valuable method in terms of how many free flights or nights you can book with a certain number of points.  But this is also where it’s easy to get stuck because it can be very time consuming to figure out the best Chase transfer partner for your travel plans.

Each airline has a different award chart, so even on the same route you can pay wildly different prices depending on which Chase travel partner you use!  And that’s not even considering that you need to find available award seats to book with points!

And the same goes for hotels.  You’d need to transfer 70,000 Chase Ultimate Rewards points to IHG to book their top-tier hotels.  While it would only take 30,000 Chase Ultimate Rewards points (transferred to Hyatt) to stay at the best Hyatt hotels.  That’s a big difference!

But Hyatt hotels aren’t nearly as common as IHG locations.  So you’ll want to make sure there is not only a hotel where you’re going, but you’ll also need to find available award nights on the dates you’re traveling.

This is a lot of moving parts to manage.  It’s easy to feel overwhelmed and get bogged down in the details of trying to squeeze more value from your points.  If this option is stressing you out, then save yourself the mental anguish and go with one of the other 2 methods.

But if you’re willing to put in the time, you can turn 50,000 Chase Ultimate Rewards points into $1,000+ in travel!  I’ll show you how Josh was able to use less than 24,000 Chase Ultimate Rewards points to book $650+ in airfare and hotels.

Making Josh’s First Miles & Points Trip a Success

Josh’s first instinct was to pay for his travel with his Chase Ultimate Rewards points through the Chase website, which isn’t a bad choice.  He would have used fewer points than if he redeemed for cash back toward airfare and it would have been almost as easy.

But because he was booking his flight fairly last minute, the tickets were pricey for a short-haul domestic trip.  Still, I imagine he would’ve felt pretty good getting a free ~$700 flight, even if it would’ve cost ~47,000 Chase Ultimate Rewards points.  That’d be way better than my first miles & points award!

To save on flights, the first thing we did was check with the Chase Ultimate Rewards transfer partner Southwest.  Southwest doesn’t have set prices for their award flights, so the number of points you pay varies depending on the cash price of the flight.  Josh was able to book what would have been a ~$151 round-trip ticket for less than 9,000 Southwest points (transferred from Chase at a 1:1 ratio) + ~$11 in fees!

The flight times weren’t ideal and he had to be a bit flexible with his schedule to book the cheapest flights.  But it worked out great and gave him more time to explore the city after his tournament.  And he saved a ton of Chase Ultimate Rewards points because typically you’d need to transfer 15,000 to 25,000 points to book the same type of award with other airlines.

Pro Tip:   Southwest flights won’t show up on any 3rd-party sites (i.e. Google Flights, Expedia, Chase Travel Portal), so you’ll have to check their site directly to see their prices.  And you can book Southwest flights through the Chase Travel Portal, but you’ll have to call to book.

The Ultimate Frisbee tournament was in the suburbs, so he needed a hotel for 3 nights.  I looked to see if Hyatt had any nearby locations because you can book the lowest category Hyatt hotels for only 5,000 Hyatt points a night!  In the end, Josh got 3 nights at a nearby Category 1 Hyatt House for 15,000 Hyatt points.  The same rooms were going for ~$170 a night, so he avoided a hefty $510+ bill by transferring his Chase Ultimate Rewards points to Hyatt at a 1:1 ratio.

And on top of that, Hyatt House hotels have, in my opinion, the best free breakfast of any hotel – you can’t beat free made-to-order omelettes (at most locations) every morning!

Including the Southwest flight, he was able to book ~$660 in travel with only 24,000 Chase Ultimate Rewards points!  And the best part is, we had this all figured out in ~20 minutes.

Could we have done even better?  Would it make more sense to pay cash for the cheap flight and use the points for a more lucrative award?  Sure, but to be honest the answer to that question is just about always going to be yes.  And at some point you need to value your time enough to just book the trip.

We booked this trip so quickly and efficiently mostly because I have traveled that route a bunch of times before and had a good understanding of the best options.  In other words, I have booked a lot of over-priced awards on that route before and learned from my mistakes.

But if we both had been starting from scratch, we could have easily spent hours combing through award charts, calculating the best options, and searching for available award seats.  So you can see how in that scenario it can make sense to skip all the effort it takes to book the “best” award and instead to pick the low hanging fruit, even if it costs you more points.

Bottom Line

No matter what your travel goals are, there are miles & points that can get you there cheaply.  Earning flexible points, like Chase Ultimate Rewards points, makes the most sense because they will give you more travel options.

But all those options can be overwhelming.  So if you’re stuck and haven’t pulled the trigger on your first award flight or free hotel stay, then you should simplify your strategy.  A “bad” award flight you book (can free or cheap ever actually be bad?) is better than the best award you never get around to booking.

If you’re looking for your first travel rewards credit card, I recommend the Chase Sapphire Preferred card.  It earns valuable Chase Ultimate Rewards points that are so simple to redeem, you’ll earn no less than $500 from the card’s sign-up bonus the first year you have the card!

What is the trip you want to take but haven’t made because it seems too confusing book?  Let me know in the comments and I’ll help point you in the right direction.