Let’s be honest. We all have that one friend.

You know the one. They make a normal salary, yet show up at every destination wedding and somehow spend their PTO drinking vintage Krug in a lie-flat seat on the way to the Maldives.

Meanwhile, you’re in row 34, knees crushed against the seat in front of you, wondering if you have to pay extra for water.

I used to think these people were either secretly trust-fund kids or selling feet pics. Turns out, they just speak a different language: points and miles.

If you’ve avoided this world because it feels like you need a PhD to book a flight, you’re in the right place. At Departure Digest, we don’t do 20-tab spreadsheets. We do champagne taste on a Two Buck Chuck budget.

This is your crash course. We’re going to strip away the jargon and show you how to turn everyday spending into flights, your rent into hotel stays, and your business trips into family vacations.

Once you understand a few core ideas, the whole thing gets way less intimidating.

At their core, points and miles are just rewards currencies. Think of them like arcade tickets. You play the game (spend money), you win tickets (earn points), and eventually, you trade them in for a prize (a flight to Paris).

People use “points” and “miles” interchangeably, but there are three buckets that matter.

Airline miles come from airline loyalty programs (like Delta SkyMiles or United MileagePlus). You earn them by flying, using certain cards, or earning through partners.

You generally redeem them through that airline’s program, even if the flight ends up being on a partner airline (more on that soon).

Hotel points are earned through programs like Marriott Bonvoy or Hilton Honors. 

Hotel chains are huge “families” with a lot of brands under one umbrella. So, a basic work stay can still earn points that you can later use at a nicer resort.

This is the gold standard for beginners.

Transferable points are the flexible points you earn from certain rewards cards. They’re called transferable because you can move them to airline or hotel programs, so you’re not locked into one brand.

Common examples include:

If you only remember one thing today, make it this: Flexible points are the best starter currency. Because you can transfer them to different airlines or hotels, you aren't locked into one specific brand before you even plan a trip.

There’s a massive misconception that you need to fly a lot to earn a lot. Not true. Most points are earned on the ground.

You could take a flight from New York to London and earn 3,000 miles. Or you could earn 60,000 to 100,000 points from a welcome bonus without stepping into an airport.

That’s why rewards cards matter, as long as you use them responsibly.

Before you earn a single point, you need to understand value. Not all points are created equal.

Fixed points are like store credit. If you earn Delta SkyMiles, you’re mostly using them for Delta and its partners. If you earn hotel points, you’re mostly using them within that hotel family.

Transferable points are more like a flexible currency. You can move them to different airlines or hotels depending on who has the best deal for your trip.

For example, let’s say you have Chase Ultimate Rewards. You could transfer them to United MileagePlus for flights or transfer them to World of Hyatt for a hotel stay. If you only earned United miles, you wouldn’t have that hotel option.

Points do not have one fixed price tag. The value changes based on how you use them.

Here is the simplest way to check if a redemption is "good" or "bad" using the "cents per point" math:

Cash price ÷ Points price = Value per point

If you’re getting 1 cent per point (i.e., a $500 flight costs 50,000 points), that is a standard "fixed" redemption. It’s easy, but it’s not amazing. The "champagne" value comes when you transfer points to partners, where you might get 2 cents per point or more.

Here are the beginner-friendly ways to build a balance fast.

This is the fastest infusion of points most people will ever get. Many travel cards offer large bonuses if you spend a certain amount in the first few months.

If possible, it can be smart to time a new card with a planned expense, like wedding expenses, a tax bill, or a move.

Different cards reward different spending.

You don’t need a complicated setup. Even one or two smart choices can make a big difference.

If you’re not ready to open a new card, you can still earn real rewards.

Okay, you have the points. Now, how do you use them? 

You generally have three options.

This works like Expedia. You log into your bank’s travel site, search for a flight, and pay with points.

Some programs let you book travel normally with your card, then use your miles to offset that specific charge later. This is great for beginners who just want to keep it simple.

This is how people fly a $10,000 business class seat for just the taxes and fees. Instead of booking through the bank, you transfer your points to the airline’s loyalty program and book an "award ticket" directly with them.

Real-world example: A flight to Europe might cost $1,500 cash. In the bank portal, that might cost you 150,000 points. But if you transfer those points to an airline partner (like Air Canada Aeroplan or Air France/KLM Flying Blue), you might find that same flight for only 60,000 points.

The beginner-friendly booking flow:

Just like cash prices for flights and hotels change, points prices change, too. This is called dynamic pricing. However, some programs still use award charts or price ranges, meaning a luxury hotel night might have a maximum points price regardless of how expensive the cash rate gets. This is typically where you find the best value.

Also, know that you can technically redeem transferable points for cash back, gift cards, or merchandise. However, we rarely talk about those options because the value is almost always terrible compared to travel. Friends don’t let friends burn valuable points on toasters.

You might be thinking, "But I don't fly Air France." Here is the cool part: You don't have to.

Airlines have teammates. The three big global alliances are Star Alliance, SkyTeam, and Oneworld.

Hotel chains are huge. Marriott Bonvoy is not just “Marriott.” Hilton Honors is not just “Hilton.” Each program includes a mix of brands at different price points. This matters because you can earn points on practical stays (like a Hampton Inn) and redeem them on aspirational ones (like a Waldorf Astoria).

Having the right travel credit card isn't just about the points; it's about the lifestyle upgrades. Even mid-tier cards often come with perks that make travel less stressful:

Here’s the process I use when I want something simple and repeatable.

Pick one trip goal Not “travel more.” Pick something specific, like a long weekend in Miami or a family visit to London. A clear goal keeps you from collecting random points with no plan.

Open your core loyalty accounts Make free accounts with one or two airlines you actually fly and one or two hotel programs you’d realistically stay with. Save your login info somewhere safe. Future you will thank you.

Start earning in the easiest places first If you want a low-effort setup, do these today:

[Link to Bilt Rewards]

Decide if a rewards credit card makes sense If you pay in full every month and can hit a bonus with normal spending, a starter card can speed things up. If not, keep earning through the free options and circle back later.

Search before you move any points If you’re transferring points, find the exact trip first. Then transfer. Then book.

Book, then stop refreshing Award availability can change fast. So once you find the trip you want, do not overthink it. Book it, screenshot the confirmation, and move on with your life.

Travel rewards require a little organization and a shift in how you pay, but the first time you sip a pre-departure drink in a lie-flat seat, you’ll wonder why you waited this long. Start small, pay your balance in full, and we’ll see you in the lounge. 🫡