If you read my last post, you saw that I managed to put together a 2 week trip to Japan (with a few days in Taipei) for two people that’s costing me very little out of pocket. We’re staying in nice hotels, and traveling (in comfort) via airplane and train, mostly using miles and points. This post is where I explain how to get started collecting miles and points.

Obviously I use sharing economy travel services for a lot of my travel needs: most of my lodging comes from home exchanges, much of my overland transportation is through ridesharing, I often deliver stuff carried in my luggage to people who pay me in either money or useful services (like a ride from the airport, or tickets to something fabulous), and I enjoy activities like food tours that I book through peer-to-peer tour sites. But this doesn’t cover all of my travel expenses. There is the cost of getting to my destination to consider, especially when flying long distances. Sometimes I need to stay in a hotel because I can’t find a suitable house swap. And finally, I take trains or busses for overland travel. Many of these expenses I cover by using miles and points.

Back in 2014 I wrote an overview post about how to get free flights with miles and points. I went back to it recently thinking I’d be embarrassed by how much I’ve learned in the past two years, but actually it’s not bad. However, a lot of things have changed in the past few years, and I have learned a lot, leading me to change my approach a bit. As with most things, the more you learn the more you realize you don’t know.

There are ways to dive in to this hobby deeply and earn an insane number of miles and points. You can travel in first class and stay in super fancy hotels all the time. But for this you will need a pretty significant investment of time, and also some investment of money. If you just want to take a few trips a year, this is possible without a crazy amount of work and very little cash investment.

Types of Miles/Points

Your goal here is to accumulate miles and points that can be spent on travel, and then to maximize your use of these by redeeming for flights and hotels that give you the best value for your points. There are several types of miles and points to collect:

  • Airline miles (i.e. American Airlines, Southwest)
  • Hotel points (i.e. Hyatt, Marriott)
  • Third party points that can be transferred to airlines and hotels (Chase Ultimate Rewards, Citi Thank You, SPG, and Amex Membership Rewards Points)
  • Third party points that can be redeemed directly for travel (i.e. Flexperks, Arrival points)

To get started, Travel Is Free has a good (though now a bit dated) overview of these different types of miles and points and how they interact. If you don’t have accounts with all the major airlines and hotels, you should create them now. You can also sign up for an account with one of the tools out there that will track all of your accounts for you like Award Wallet. (Here’s a free upgrade coupon for the first 7 people who sign up to Award Wallet: free-hnifye). Or just make a spreadsheet of all these accounts so that you don’t forget to use them to get credit for all your flights and hotel stays. Those points can add up!

But just getting credit for paid travel is a very slow way to earn miles and points. You really want to supplement this by getting big bonuses from credit cards, and earning miles or points for all of your spending. That’s where things get interesting.

Credit card bonuses

It is well worth your time to do some research to become familiar with the various miles and points credit cards and credit card bonuses. I started off rather stupidly in this hobby by just signing up for a credit card whenever the BIG bloggers said I should. It turns out, they get paid in referral bonuses for pushing credit cards. So leaving it up to them to decide when you should sign up isn’t a very good idea. I like Doctor of Credit’s master lists of best credit card sign up bonuses (for both personal and business cards) along with DOC’s list of best current offers. DOC doesn’t do referral links so you can trust this data.

You also need to get an idea for bank rules; they’ve become a lot more restrictive over the past year or two and if you don’t pay attention you can make yourself ineligible for some of the most lucrative cards.  DOC also has a good master list of these rules and which cards can be opened and closed multiple times. A good example here is Chase. They now have the infamous 5/24 rule: you can only get a new card if you have opened fewer than 5 new credit cards in the past 24 months. So it’s a good idea to get the best Chase cards first, before you start applying for other cards and end up hopelessly over this rule.

You’ll also need to figure out which credit cards give you bonuses for which types of spend. For instance, you might open a card that earns 3 points per dollar on restaurants. So you obviously want to use that card for all your eating out. There are a lot of different types of bonuses out there on top of the initial sign up points. This is part of familiarizing yourself with your credit card options.

If you’re still paying attention, perhaps this hobby is for you. If you’ve eyes have glazed over already, all is not lost. If you travel a lot you probably have a friend who is in to collecting miles and points. Ask them for advice about which cards to open. That’s a good place to start, which should help you avoid making the wrong choices that you’ll regret later.

Award redemptions

Once you’ve started accumulating lots of miles and points, you also have to learn about how to redeem them. You could just go on the airline’s website (for instance American Airline) and book that ticket to Miami and feel good that you only paid a few dollars in taxes for your flight. There’s nothing wrong with this. But if you really want to maximize the value of your redemptions there are lot of tricks and nuances. For instance, American Airlines doesn’t show you availability on all the partner airlines that you can book with their miles, so you need to figure out where you can search for this space (hint: BA and Quantas). Here’s a decent overview of where to search from View From the Wing and a nice (but slightly dated) chart from Travel is Free.

You should also spend some time looking at the relative value per mile you’re getting. If you pay 25,000 miles for a ticket that would have cost $300, that’s not nearly as good as 50,000 miles for a ticket that would have cost $2k. Of course if you don’t have $300 and want to take that flight, by all means use the miles! But sometimes it might be worth paying cash for a ticket if you can afford it. Everyone has to come up with their own valuation based on what you can afford, and what travel you aspire to.

Last step: enjoy your (almost) free travels!