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MTM101: Points & Miles For Beginners–Part 5: Your First Trip Using Points

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MTM101: Points & Miles For Beginners–Part 5: Your First Trip Using Points

MTM101: Points & Miles For Beginners–Part 5: Your First Trip Using Points

In Part 5 of our Points And Miles For Beginners series, we will learn how to book your first trip using points & miles. We will cover a few key points. First, we will look at some great websites you should bookmark for booking your trips. Second, we’ll use these tools to discover how many points & miles you need for a certain trip. Third, we’ll learn how to transfer your points to a hotel or airline program, plus we’ll learn how to search for trips in the Chase travel portal. This way, you can use your points for the best value. Lastly, we’ll look at some sample award searches to see how this works.

Recap From Parts 1-4

  • In Part 1, we understood the gist of this hobby. We got our credit profile updated, we understand how credit works, and we answered some common questions.
  • In Part 2, we applied for our first credit card. After it came, we activated it, enrolled for whatever perks it comes with, and now we are using it. We also created a system to stay organized and track all the information about our new credit cards.
  • In Part 3, we talked about business credit cards and what counts as a business. We also signed up for loyalty program accounts with airlines and hotel chains, since we’re going to start using those for our free travel soon.
  • In Part 4, we talked about hotel credit cards and looked at some common options. We talked about how hotel credit cards have different perks from general “rewards cards” and will provide combinations of ‘free nights’ + points.

At the end of Part 4, your homework was to start thinking about your first trip using points & miles. We asked you to think about where you’d like to go. Now that we’ve dreamed, it’s time to start making that dream come true.

Websites To Help With Booking Trips

Thinking about points & miles, keeping track of your credit cards, due dates, points…it can feel like a lot. That’s why we’ve talked about being organized a few times. You don’t have to use my system. Find something that works for you, then use it. However, there are a few websites I find especially helpful when it’s time to start booking a trip. As you prepare to take your first trip using points & miles, I encourage you to use these and bookmark them for later.

  • Award Hacker – Award Hacker shows you estimates of how many points & miles you’ll need for flights. Type in where you’re flying from & to, choose one way/round trip, and what class of travel you’re looking for.
  • Award Mapper – This site shows hotels in a given city that can be reserved using points. Scroll around to see their locations. Click on the hotel for its name, what loyalty program its in, and an estimate of how many points you need per night.
  • Award Wallet – You should have this set up already (it was homework in Part 3!). Keep track of your loyalty numbers and points balances for airline, hotel, rental car programs & more.
  • Chase Travel Portal – Since we’ve been earning points through Chase Ultimate Rewards, here is where we can see how many points we have & search for ways to use them. Redemptions include gift cards, cash back, guided tours & more. You also can use your points to book hotels & flights.

There are tons of other great websites in this hobby that you’ll likely bookmark along the way. However, there’s already a sense of being overwhelmed, so let’s not add to it. These websites will give you a great starting point to search for your first trip using points & miles.

How Many Points Do You Need?

“How many points do I need?” Great question. I wish there was a definitive answer. It can change depending on multiple factors. Are you going at a busy time? The hotel might charge more points for “peak season”. Is this hotel luxury, mid-range, or budget? What about your flights — first class, business class, or economy seats? Are you flying on a Tuesday in February or is it Christmas time? All of these can change how many points you will need for the flight or hotel you want to book.

How many points do you need for your first trip using miles?
Award Hacker basics when searching for award flights.

Finding An Estimate On Points Requirements

This is where Award Hacker can really help us. It’s not perfect; understand that from the beginner. It can’t promise you anything, but it can give you a great starting point. Here’s what settings you can use for your flight searches:

  1. From – you can type in a specific airport or type in a city and use all airports in the area.
  2. To – specific airport or city with multiple airports.
  3. Round trip or one-way – some programs require round-trip bookings & others charge less for round-trip than 2 separate one-way bookings.
  4. Cabin – search by economy, premium economy, business, or first class.
  5. Stops- how many stops you’ll accept on the trip (direct, 1 stop, or 2 stops).
  6. Frequent flyer program – do you only want to see results from specific program(s)?

Notably absent: number of passengers and dates. Why? This tool shows you how many miles you can expect to pay in typical situations. It doesn’t tell you if flights are actually available, so that’s why the number of passengers and dates aren’t included. For example, Award Hacker will tell you that an average flight for the cities you chose costs 20,000 miles, but you might find nothing or find flights for 30,000 miles on the dates you want.

Note: since we’re starting out, you may only have points / miles with Chase Ultimate Rewards. You can filter for that in number 6, so you only see airline programs that can be booked with the points you actually have.

Portal vs Transferring Points

The 2 most common ways to use your points for trips are through a travel portal or by booking with the airline after transferring your points to them. In this section, we’ll see how those are different and also how to compare which option is better in any given scenario.

Chase Travel Portal

After earning your Ultimate Rewards points from Chase, they are in your Ultimate Rewards account. Once you are logged into your credit card account with Chase, scroll down and click on where it shows the number of points you have. Inside the points portal, click on where it says “Earn / Use” at the top, and choose ‘travel’. From here, you can choose the type of travel you want to search for.

When searching for flights and hotels in the travel portal, you are using your points against the cash price of what you’re booking. This is where using the 1.5 cents value of the Chase Sapphire Reserve or 1.25 cents value of the Sapphire Preferred helps you. Other cards only give 1 cent per point value.

After searching for a hotel or flight, you’ll see a cash price and right next to it a points price. Because you are effectively paying cash on flights this way, when it comes time to fly you’ll also earn miles in your frequent flyer account. When you book ‘free flights’ using miles, you don’t earn miles. Because the airline sees bookings from the travel portal the same as cash tickets, you will earn miles!

Transferring Points To Loyalty Programs

The 2nd option is transferring your points. This is why we refer to Ultimate Rewards points as ‘transferable’: you can send them to numerous different airline and hotel programs. After seeing how many points Chase wants for that hotel or flight, see what you’d pay to book directly with an airline or hotel itself. Is it more or less? Do whichever makes sense for you.

If you need to transfer points, you can only do that from a paid version of points-earning cards. This means the Sapphire Preferred, Sapphire Reserve, or the Business Preferred cards. In the portal, click on ‘Earn / Use’ and look for the ‘Transfer to Travel Partners’ option. On the next page, you’ll provide the info of the program you want to send your points to, such as the name on the account, the account number, and how many points you want to transfer. You must transfer in increments of 1,000 points.

Combining Points

A cool thing about Chase is that they allow you to combine points with those living in your home. This provides 2 advantages: 1) you can put all of your points in 1 place, so you don’t have multiple different reservations, and 2) you can put them into the account that gets the best value. If making a booking in the Chase travel portal, I send my points to my wife’s Sapphire Reserve account for the best value. If transferring points to an airline or hotel, my wife sends her points to my account, since I’m more familiar with the process. To combine points, look for ‘Combine Points’ under the ‘Earn / Use’ options.

2 Examples – Your First Trip Using Points & Miles

Now that we know a little about ‘how many points do I need?’ and the ways to actually redeem your points, it’s time to book your first trip using points. For this exercise, I’ll show 2 examples, so you can see how to get started. The principles work for your trip, so you can follow along.

Using your Ultimate Rewards points to fly to Hawaii.
Estimated points values for round-trip tickets between Chicago and Honolulu.

Couples’ Trip To Hawaii

The image above shows estimates from Award Hacker for round-trip flights between Chicago and Honolulu. You’ll immediately notice there are tons of abbreviations. When in doubt, Google it! Our cheapest price is “SQ miles” — what are those? SQ is the abbreviation for Singapore Airlines, and their program is KrisFlyer. The colored boxes on the right tell me all the different types of points I can transfer to KrisFlyer. In the middle, we see “operated by”, meaning which airlines are actually flying me to Honolulu. AS=Alaska Airlines.

This is where points & miles gets weird. My cheapest estimate is to send my points to Singapore Airlines…in Singapore…to fly to Hawaii…on Alaska Airlines. Yes. Many times, you will use your points to book using partnerships. Use your points with airline A to fly on airline B. Unfortunately, Singapore Airlines doesn’t allow for booking flights on Alaska Airlines via their website. You can contact them here.

It’s worth the phone call. For comparison, if you just wanted to book online, you’ll pay a lot more miles.

Using KrisFlyer miles to fly to Hawaii in economy.
Using Singapore KrisFly website to book Chicago to Honolulu.

If you book via the Singapore Airlines website, you’ll pay 17,500 per person per flight. That’s 35,00 round trip, so 70,000 miles for the 2 of you. Singapore would have you fly on United Airlines this way.

Using United miles to fly to Hawaii
Chicago to Honolulu using United MileagePlus.

If you’d use United’s own website to book these flights, you’d pay even more. United wants 22,500 miles per person per flight. 45,000 miles per person, so 90,000 total. It’s worth picking up the phone to pay only 25,000 miles per person!

Using points for hotel stays in Honolulu for your first trip using points & miles
Hotel options using points in Honolulu.

Hotels abound in Hawaii. Depending on where you’re going and how fancy you want to be, as well as the time of year you’re going, you’ll pay more or less points. This is where Award Mapper can help us spot out some hotels in the area. While we can book hotels from IHG, Hyatt, and Marriott with Chase points, the best value is usually with Hyatt. Since our points will transfer 1:1 to any of those programs, the cheapest is the cheapest.

After I put in my destination city, Award Mapper showed me a TON of hotels. On the left side, I turned off hotel programs I can’t book using Chase programs. Now, I can see only Hyatt, IHG & Marriott. On the right, I can scroll (more off screen) through hotels by name and estimated number of points. Points estimates are obviously for a standard room, so you’ll need more for things like a suite, preferred views, etc. Map markers show me where the hotels are.

The other way to find a hotel is starting from the other side. If there’s a specific hotel or hotel program I want, I’ll just go to the website of that hotel chain and search from there. Once I’m on the hotel website, I can find availability and number of points needed. Make sure to compare this to how many points you’ll need when booking via the Chase travel portal!

Note: remember that we said using the Chase travel portal earns you miles on flights? It earns you nothing on hotel stays. You need to book directly with the hotel to get credit for staying there when accruing nights in their loyalty program, earning points with them, etc. You might get lucky by asking at check-in, but it’s not a guarantee and not required. If points / prices are the same, book directly with the hotel.

Family Trip To Disney World

Our 2nd example for your first trip using points & miles is a family trip to Disney World in Orlando, Florida. For the purposes of this example, we’ll assume 2 adults, a 4-year-old & a baby are your “family”. Your fictional family lives in Denver.

Award Hacker estimates for Denver to Orlando


From Denver to Orlando round trip, Award Hacker says our best bet is starting with United. Remember that we filtered for Chase Ultimate Rewards on the right side, so that we’re only seeing programs that work for us. If you’ve got points of other types, you can adjust these settings.

United flights Denver to Orlando for your first trip using points & miles

United has numerous direct flights to choose from, and you’ll pay only the mandatory $5.60 tax per ticket. 25,000 miles per person round trip means 75,000 miles for the 2 adults and the child. The good news is that lap infants fly free on domestic flights, so you’ll save money and points here. While child tickets (at a cheaper price) exist with some airlines, you’ll pay the same amount of points for an adult or a child in most cases. Adding children & their ages is done in the ‘advanced search’ area.

Using the Chase travel portal DEN to MCO

Interestingly, you’d use less points booking this trip through the Chase travel portal, if you have the Chase Sapphire Reserve. You’d pay 70,040 points, which is a savings of 4,960 points + $33.60 in cash. Note that the cheapest fares in the portal are for basic economy. You can read our overview of basic economy here and also a look at what it’s like flying basic economy with kids.


There are numerous hotels near Disney’s parks. In fact, the number of options can be overwhelming. Many people want to stay at the hotels owned by Disney, because of increased perks like extra hours at the parks, free shuttles, etc. However, you can get those perks and also save money / use points. This sweet spot is with Disney-affiliated properties.

I recommend you check these out. Earlier this year, we stayed at the DoubleTree from Hilton right near Disney Springs. We stayed there using points, got free shuttles to the parks, got the extended park hours, and also saved money. There are Disney-affiliated hotels with these perks that are owned by Hilton, Marriott, Wyndham & IHG, all of which have programs where you can book your stay with points.

Going Forward – What’s Next?

Now that we’ve looked at examples of how to book your first trip using points & miles, it obviously leads to the question of “what’s next?” Hopefully, this is a launching pad. We previously looked at deciding between a few different credit cards, so now you understand a bit about the process of evaluating which card to get next.

We looked at how to go about booking a trip, so you understand the basics. Sure, trips can get more complicated, but now you know how to get started. Brain storm, ask some questions in our Facebook group, and use these tools to start booking.

I also previously mentioned working in “2-player mode” with my wife. You can get cards that compliment one another. You can take turns getting credit cards, also, which helps your credit report cool down a bit, since banks don’t like to see you opening a bunch of cards too quickly.

So, what’s next? Next is reading, learning, finishing the spending requirements on your current card and then moving on to the next one. The best bang for your buck is to always have a new credit card you’re working on, putting every dollar you spend on it, paying the bill, and then earning that massive welcome offer. Another thing you can learn about is using shopping portals to earn extra points/cash back online, which is why I believe you should never earn just 1 point per $ spent online.

It also can be helpful to build a strategy for yourself. Thinking about your travel goals and working toward those can help you earn the points & miles you’ll need and find most useful for the trips you want to take.

Final Thoughts

That’s a wrap on our Points And Miles For Beginners series. We introduced this hobby, understood how credit works, and then jumped in. Next, we applied for our first credit card, started using the perks, and put all of our normal spending on this card to meet the requirements. We also talked about business credit cards and hotel credit cards. Finally, we looked at how to go about booking your first trip using points & miles to go on a free vacation. You now understand the basics. Congratulations! The points & miles hobby is awesome, interesting, frustrating at times, but massively rewarding. If you have questions, ask. That’s the best way to learn as you continue moving forward.

Disclosure: Miles to Memories has partnered with CardRatings for our coverage of credit card products. Miles to Memories and CardRatings may receive a commission from card issuers.

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Ryan Smith
Ryan Smith
Travel hacker in 2-player mode, intent on visiting every country in the world, and can say "hello" or "how much does this cost?" in a bunch of different languages.

Responses 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.


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