Skip to main content

money & life

Make Your Dream Trip a Reality

Lesson 5 of 32

Earn Miles While You Sleep

Chris Guillebeau, Stephanie Zito

Make Your Dream Trip a Reality

Chris Guillebeau, Stephanie Zito

buy this class


Sale Ends Soon!

starting under


Unlock this classplus 2000+ more >

Lesson Info

5. Earn Miles While You Sleep
Learn how the Rewards Network operates and how joining can help you earn free airline miles!

Lesson Info

Earn Miles While You Sleep

What we're going to look at this week is how to earn points and miles while you sleep we're gonna look at that today possible it is really got it e I hope it is otherwise we have this president we're going to help you learn how to get really big mileage bonuses in our third lesson this week we're going to look at how to maximize points and miles credit cards and the goal for this week as a whole is to get you on track to earning hundreds of thousands of points and miles so you can actually plan your dream destination today's lesson is earning wiles mont earning miles while you sleep and as you know we've got three goals for each lesson today's goals are to learn the best ways to earn miles right now to register, turn ongoing dining rewards and understand how you can shop online to get miles awesome sounds great so when it comes to earning miles, scott asked a question in the previous lesson last week about how he normally likes to earn miles in alaska he's wondering about how that's go...

ing to affect his status et cetera it's that are a lot of people have this misconception of how most miles are earned, so I'd actually like to ask the audience how long do you think the average flight iss in north america in miles you have a gas? Just raise your hand no one has a guest. Well, what do you think? Six hundred six hundred. So what do you want to say? Casey six fifty? Anybody else wanna guess? Like over under now that was saying one hundred miles miles might be a little more than that. Actually, it is a relatively low number. Any other guesses? It's good, you guys are actually pretty close I'm saying why everybody I'm calling it's got my my averages starts about fifteen hundred okay, but he's flying from alaska mostly to the mainland, you are somewhere else? Okay, so the point is you guys were actually really close to average flight in north america is seven hundred and fifty two miles. The reason why we point us out is it's actually not a lot of miles in terms of all the miles and points that you're going to earn, like it's a far distance if you get in a car and drive seven hundred miles but it's actually really, really easy to earn a lot more than seven hundred miles or a thousand miles or even fifteen hundred miles through all the different things that were going to teach you in this course. So most miles are actually earned on the ground through non flight activity and it's our goal this whole week to help you set up a system to turn everything you eat, drink and buy into points and miles this is something that we're gonna work on today. Tomorrow next lesson and we're going to begin by looking at dining does anyone like to eat? Okay, good. I like to eat so everyone here likes to eat. How many people here before coming to this lesson today had already signed up for rewards network raise your hand and no one is raising their hand. Maybe one person that's great! I know you signed up great to clarify when you say rewards network what do you mean by that? Rewards network is a very specific program it's a program in which you can earn miles for the restaurants that you already go to. All right, this is a very, very simple thing that everyone here and everyone watching I can do right away. It has a grand cost of zero dollars. You never have to do anything for it. Other than sign up on the website and rewards network has partnerships with, I believe about a dozen or so airlines and hotels you choose which one you want to earn your miles or points, and then they have further partnerships with I think tens of thousands of restaurants and once you're signed up and wants your credit card to your debit card is linked could be any card doesn't matter what kind you'll automatically earn bonus smiles and points whenever you dine at these restaurants don't have to do anything else, you just sign the bill at the end like you always do so you can visit rewards network dot com slash earn for a complete list on, by the way, we're going to be talking about a lot of links throughout this course, as we mentioned last week and going on further so you can also go to our links. Paige travel hacking dot org's slash dream trap we'll be putting everything there but rewards network dot com slash earned you can earn miles and points with american, united or delta with alaska southwest spirit. If you prefer hotel points, you can get hilton and I it's actually a number of other partners as well. Air canada used to be part of it that they left, but you could still earn miles with a number of the u s airlines and then the way it works, as I said, you just sign up, you link your credit or debit card, any of them will work, you can actually link more than one on. Then every time you dine at a participating restaurant, automatically earn points for miles, you don't have to do anything else and there's thousands of restaurants, okay, so a couple of tips about this again super simple everyone should do this because there's no reason why not to you register your cards just in case if you get an extra credit card, if you have a debit card or something that you don't usually use when you go out to dine, you might as well just registered in case it's just three miles and points all of these programs offer a sign up bonus sometimes it's two thousand miles sometimes it's one thousand could be more for something special. So again, the average flight is seven hundred fifty two miles. Just by registering your card and having one qualifying visit to a restaurant, you're actually really more miles on that just write off talking about so that will happen with your first time learn which restaurants to frequent or suggest if you're dining out with friends, maybe you want to suggest a restaurant that's part of the dining rewards network, and if you are with your friends, maybe you want to pick up the check and get reimbursed? Not necessarily if it's like an awkward or difficult thing, but if you're in that situation and somebody's going to pay the bill, why not it be you and you get paid back and you'll learn all those points and then if you dine more than once, if you actually done a number of times in particular year like most of us do you start earning bonus points so you can actually twelve points for every dollar is a twelve it's five signed three points per dollar thank you and after you've completed twelve dines in one year, you'll earn five points for dollars so if you go to a restaurant and you spend twenty bucks, you'll get one hundred bonus points solely because you've registered in this program and one of the other things is when you go to that when you go to the dining miles page for your airline, you'll see a list you can search by zip codes and see a list of all of the restaurants in your neighborhood and a lot of these are restaurants you probably already go to and with the twelve qualifying dines there's a coffee shop in the rest in the neighborhood where my family lives in every day I went and bought my coffee there and so I was earning an extra thirty or forty points just by buying coffee from a coffee shop I already went to so once you have twelve dines as we mentioned stop dying that's where I came from what you have dines in a single year you'll earn those extra points five points for every dollar spent this leads to a challenge something that stephanie and I put together maybe two years ago for the first time we called it the dining dash not to be confused with dine and dash where we attempted to visit all twelve restaurants in a single day just for fun I think that first year we only made it to ten but then we repeated the challenge this year with tyler to born our adventures are the trouble hacking cartel and all three of us actually made it to twelve restaurants and a single day, so that was kind of fun but you don't have to do that. All you need to do is register and link your card and then you're automatically gonna be earning points so that's how you can earn miles and points for all of the dining that you already d'oh and just a point of clarification with the linking your credit card it's not actually charging anything to your credit card, all it is is that's the way when you pay with that credit card in a restaurant. If that restaurant is in this program, it identifies you and sends points there so it's not using your credit card for anything I'm glad you pointed out it looks like bill might have a question about that picture looks like you're in a food truck in portland I'm trying to figure out that's exactly right theo, I've grilled on dh I think the downtown older area of southwest portland that's the only food cart that we know of including that accepts credit cards now there's two wait obviously we sought them out so you know that girl I don't know that girl, but they have to be registered in the program, yes, but I'm trying to figure out how many, you know, small, independent, you know, poor lana's style, a lot of the restaurants. So, yeah, if you go to the website and put in the zip code, you'll see a whole directory and you can actually do it with the app and use to turn your location services on it will show everything in the surrounding area following questions that you double up your miles by paying with a credit card, then absolutely generates my absolutely used in this case for dining. I'm using my chase sapphire afeard cards, I am earning double points for that. We'll talk about that in the next lesson to cum. So, yeah, I'm earning points and earning points. Its documents, yes, is it at one specific location or total in the program? Great question total in the program, you don't have to go to the same restaurant twelve times. You can if it's, a coffee shop that you frequently visit, but it's twelve in the total program. For me it's kind of fun this happens automatically a lot like I'm traveling on the road I'm doing stuff I don't even use the app I don't even look up a restaurant I just end up getting somewhere and then a week later I get a notification that says oh I earn bonus points because that was a member of the program so it's just a fun kind of automatic spend kind of thing I think chris mentioned this you know, knowing which which places are in the program and suggesting them how many of you guys have ever been like out with a whole group of people and you're like where do you want to eat where should you wait where where should go and you're like paralyzed with indecision and I actually when I lived in washington d c there was a great a bar on the street where my office was people would always be like worse we go for happy hour might be like let's go to this bar and we would go there and everybody would pay me with cash and I have like a thousand miles by the end of the night from everybody's happy hour drinks so you know and a lot of times I made extra money off middle too you never know you could learn all kinds of things on creative so that's dining super easy for you to dio and I think we also want to talk about outing as well I'm gonna head over to you for that wonderful so we all eat and we all shop some of us were really like the shop how many of you guys really like the shop? Maybe okay, so um I personally don't really love to shop, but one of the things I've learned is for anything I need to buy whether it's something a pair shoes, a new dress you know, a computer software to do my taxes everything I actually need to buy there is a way to earn miles for it you're probably familiar with the idea because you asked about it already about using your credit card turned miles we're not actually talking about that what we're talking about right now is how to earn bonus miles from anything you shop for online so every single airline just like all the airlines have a dining program almost every single airline has a shopping mall program and not on ly airlines in the us but actually quite across the board you confined the shopping mall program and this is an example of united mileageplus shopping mall program so you we have the links for all of the shopping mall programs at trouble hacking, travel, hacking got orc slash creative live sorry trouble hacking dot org's slash dream trip and you can go to any of these mileage programs and what you'll see when you get here is basically it's a it's a portal, we call them the shopping portals and you'll see a list of all kinds of different stores and most of these air stores where you probably already shop and what you d'oh is before you buy anything anywhere, you visit your airline shopping portal and you look for whatever you're going to buy you look for the store who lists in the list of merchants of the things you want to buy, so you need to go to nordstrom's and buy it new pair of shoes so I might go shop on nordstrom's online, so but rather than typing nordstrom dot com, I'm goingto go to united and click on that nordstrom butt in down there all that's going to dio it's taken me to nordstrom dot com I'm just adding one extra step, and so when I go to nordstrom dot com, I just searched for my shoes and I buy my shoes and I get bonus points for doing it. All I did is make one extra clique in the beginning, and nordstrom's usually has, like a three times point shopping bonus. So if I go in by a hundred dollar pair of shoes at nordstrom's, I'm earning three hundred bonus miles just because I've gone to this web site and clicked that nordstrom button right there. So another example this one's for my grandmother because I believe anyone can earn points a mile's even my grandmother and my grandmother's favorite store happens to be sears and seers happens to offer nine miles per dollar and most of us probably don't chop it sears unless something goes wrong in our house right? You go to sears when you're washing machine breaks when you refrigerator breaks and I go to sears when my dishwasher breaks so I went shopping for I was shopping for a dishwasher here its ears typical dishwasher the cheapest one I could find cost five hundred dollars right? So I buy I first go to the shopping portal that united shopping portal I click on ceres it takes me to sears dot com I look for whatever I want to buy I find it five hundred dollars I buy it online I get nine bonus points for every dollar I've spent, which means I get forty, five hundred bonus miles solely because I went to that united web site and clicked that sears button before I went online and bought it that's six times the average flight in america, right? You have to fly from seattle to miami and back in order to earn that many miles when you fly and so you're like, well, I don't really want to shop online to buy my dishwasher I wanna go to sears and touch it right, so I'm gonna let chris tell you a story about how he did the same thing with his mac computer. Yeah, so last year I needed to buy a new mac book, and I was pretty sure what model I wanted, but I didn't want to go and just kind of feel it, make sure. And so I went to the apple store decided about the mac book pro, which cost almost exactly two thousand dollars, and instead of just purchasing it there in the store like I went and checked it out and like, yeah, this is what I want, but while I was in the store in the apple store, you can go online. I went online to an american airlines mileage ball, you know, checked out through the apple store on purchase that mac book pro and shows, you know, local store pick up basically, and so I checked out and I was like, okay, I'm ready ready to pick it out, you know, now and I had to wait about ten minutes or something, but in doing so, you know, there was a two thousand dollar purchase I earned, you know, the two thousand points for the purchase like bill mentioned a few minutes ago, then I think that was the holiday bonus, maybe of two points for dollar spent on apple products so that was a four thousand mile bonus so instead of just turning two thousand miles actually earned six thousand miles by doing that it's another long way for something you're already buying and this isn't just for big things I like to give the example of like a pair of mittens I bought this winner from north face dot com I got seven miles extra per dollar and they were like fifty bucks men shouldn't cost fifty bucks but they do so I got a lot of points for that um another great point is during any kind of busy shopping season there's always big bonuses so this is an example of an email I got a couple weeks ago and you could see it expired on four fifteen and sixteen miles per dollar if you used hr block tax software probably a lot of you are a lot of you watching used downloaded some kind of turbotax or some kind of tax software sixteen miles per dollar if your taxes if you paid fifty bucks for attack software at this you'd be earning eight hundred points it makes doing your taxes a lot happier right and it's more miles than the average flight we talked about seven hundred fifty miles for the average flight this one action is actually bringing you more that's why we're focusing so much on all these different activities you can do that have nothing to do with flying so yes just think about think about all the small things you're buying and how you could earn miles for them lynn had a question so maybe forget he mentions how do I find out for instance about the h and r block thing how do I know okay well when you sign up for the mileage programs so for example if you want to earn miles in united you would you would sign up for the united mileage mall program and then you can either check the website when you're buying something or if you want to be notified when they have some kind of sale or bonus special you can sign up for their email list which is how I was notified of this special deal casey questions on like some of the mileage programs can you part purchase gift cards on there too on some of them yes and well actually talk a lot more about that in um two lessons from now in lesson number eight we're going to talk about mileage multiplying your mileage bonuses wonderful so just some tips for using these shopping portals know which of your favorite stores participate you know make a list of the things that you buy every month and look the first time you look at the site get just get familiar with it learn which one's participate holiday shop online pick up in the store like chris said my dad has a boat west marine happens be down the street from where he lives he needs to buy something for his boat he buys it online he picks it up down the street so you can earn a lot of miles for things that you buy in store max out the holiday inn bonus offers sometimes when you sign up for the mileage um all the first time just like the dining program you can earn an extra two thousand miles especially during the holidays if you spend more than one hundred fifty dollars or something you can earn a two thousand mile bonus there's always bonuses coming around so look during shopping seasons and if you shop a lot set the biology mal is your home page you know if you're always going online to shop and you're gonna forget set it as your home page that's for the out of control way also told the story in lesson too I believe of the man who tried to earn a million miles in a month. One of the things he did was he waited for really high bonuses in the shopping mall and then he bought things and resold them on ebay. So if you're totally out of control beyond crazy buy resell things in the shopping mall so I want to pick up on something that lin was asking about about how do I know like where the deals are? How do I know where to get my thing s o there is a website called every word dot com e v reward dot com and this is a great sight to go to. We're gonna try to see if we can do this actually live here and this is a site you go to when you're like, okay, awesome cool when you're going toe plan to make a big purchase and you're like, ok, I'm not sure what mileage small I should go through I don't want to a ton of research, I don't want to look through ten different things, whatever this is a great sight to look through. What you do is it says where your shopping and you put your answer there and it's going to give you some data in response so earlier we were talking, and I believe it was actually lin you said one of the places you like to shop what was that again? An amazon macy's, an amazon? Okay, let's, start with macy, so I'm just gonna type in macy's here, all right? You can see macys dot com and scroll down, you have to worry about all of this data, mostly what I'm looking at here at the bottom is there, it says, points programs and frequent flier miles and hotel rwanda smile there's a big bonus happening right now everybody's shopping at macy's goodbye today s o right now you could actually earn six american airlines miles for every dollar spent at macys dot com and the reason we show this comparison is there's also some alternatives like if you look at the bottom there's united airlines for two miles you know you can earn some hotel points so how do you decide how do you not get paralyzed by choice like we talked about before? All right, I would say if you are focusing your efforts on one specific program, then that's what you do, you go with that great there's a reward bonus on delta, maybe it's not as much as the one in america that's okay, I need delta miles so that's what I'm gonna do? The reason why the comparison is helpful is if you're kind of like us, you're earning a lot of points in miles in a bunch of different programs, you know, someone like myself, I have a lot of american miles, I have a lot of united miles I might look at this and say, okay, in this case, I'm going to make my macy's purchase through the american airlines mocks its three times the bonus, which is a great little comparison thing to do, and again, it doesn't take you super long let's look, I think casey you mentioned where do you like to shop target awesome let's see, everybody has something they have to buy a target even if I don't want to write so target is interesting here I can see there's a bonus through the ultimate rewards shopping quarter we'll talk a little bit about that actually the next couple of lessons that's a flexible spending program that's managed by chase if you have a chase sapphire credit card to the chase bank card are some others you might be earning points through ultimate rewards but there are some options at the bottom for amtrak points for choice privileges points in hawaiian airlines points some of these options I would probably go through the ultimate rewards on that so that's just a great resource if you're like how do I do this without like memorizing and just uh just goto tv reward dot com and that will tell you exactly where to go so I would say if you're an apprentice we've identified yourself is an apprentice the first thing to do is just to check out the mileage mall, pick one and use that to shop through once you get that and you're more enthusiast lovely lover look yourself up a little bit, you know check out evey reward try to figure out the best different places to shop by and pick up pick up in the store and so there's a lot of different options here, so moving on to our workbook activity for the day um we have a dining activity as well as a shopping activity our dining activity we want you to sign up for rewards network dining program for whatever airline you decide to focus your mileage earning lesson on and we want to you to sign up for the shopping network for whichever airline you decided to focus your mileage earning on in the last lesson great so if you're watching at home you may have the workbook you khun do this as well if you don't have the workbook that's okay you can still participate you can still go and sign up for these programs the links are on our page trouble acting dot org's livestream trip oh I think it was rewards network dot com to just sign up direct with the with the tiny organ and I'm just gonna jump in there chris and stephanie and again talking about the workbook that comes along with the class when you do purchase the on demand any time access and then you can as you said go to that class page and print it out and be working through the entire camp so that's a great resource awesome cool s o just briefly while we were talking earlier bill mentioned something about a double dip I don't think he used that phrase but basically you were saying are you are when you go to the food cart in portland and you're earning all those bonus points for your falafel are you also earning points from your credit card? Well, yes, absolutely on in a couple of lessons we'll be talking much more about that, but if you have a mileage earning credit card there's these are all in addition to those points so you can earn points one way you could earn points another way and they're just kind of keep stacking so that's that a couple of things is kind of beyond this for those who are interested, you know, if you if you don't have access to the programs that we've talked about this far in different places, there may be a store partnership will work in australia some other locations you know outside the united states and canada store loyalty program cards in some cases actually in the state of alaska if you shocked at safeway, I believe you can earn is that united miles or something it's a crazy thing so everybody in alaska there is that there's all kinds of other stuff online rewards programs with milo transfer partners there's more things out there for our canadians when we're looking at shop dot c a you can earn aeroplane miles you know for every purchase there there are ones for germany there's a tesco option for people in the uk so there are all kinds of things out there we just wanted to present the most common ones here in the beginning

Class Description

Who wouldn’t love to know how to earn enough miles and points for two airline tickets and three hotel nights? In Make Your Dream Trip a Reality, Chris Guillebeau and Stephanie Zito can show you how it's done. 

Travel feeds our creative spirits, allows us to discover new viewpoints, and fuels our work. In this class, you’ll find out how you can make your dream of journeying to the world’s most far-flung places a practical and affordable reality.

Chris and Stephanie have made it their life's mission to help others experience all the thrill and adventure that world travel can offer. In Make Your Dream Trip a Reality. 

Chris and Stephanie will help you: 

  • Master the system of Frequent Flier miles and hotel points
  • Set up a personal points-earning strategy – even if you don’t fly
  • Upgrade your dream vacation experience at no cost to you

In short, daily lessons, Chris and Stephanie will cover all aspects of how to plan your vacation including financing your trip. You’ll learn how to set your savings and point-earning strategy so you are armed with everything you need to relax and enjoy your vacation once you depart. They’ll teach you how to book flights and hotels so you get the very best experience at the absolute best rate. You’ll also get insider tips from professional globetrotters on traveling solo and as a family.

By the end of this course you’ll learn everything you need to know to save money, minimize hassle, and make the most of your travel experience.

Your dream destination, and a life of regular traveling, is now available to you – no matter your budget. 

Class Materials

Bonus Materials with Purchase

40 Ways to Use Ultimate Rewards Points

Dream Trip Workbook

7 Habits of Highly Effective Travel Hacking Couples

Dream Trip Credit Card Tracker

Upgrade Unlocked Sneak Peak

10 Tips for Travel Hacking Families

Ratings and Reviews

Student Work

Related Classes



Highly recommended! This is one of the best CreativeLive courses I've ever taken and a great value. There's a lot of excellent information here, presented in a fun and accessible way. The CL "boot camp" approach was perfect for this topic because it dispenses the material in bite size pieces with very doable action steps along the way. The corresponding Facebook group adds even more value and camaraderie. It's a great place to clear up any questions or confusion that may come up. What an amazing resource! By the end of the course, not only will you have learned a tremendous amount, you will actually have something tangible to show for it!

a Creativelive Student

This is a fabulous course. Stephanie and Chris are both so knowledgeable, helpful, and easy going. They clearly love and practice what they're teaching. And they're open to learning from the students too. The course is packed with information, delivered in an immediately useful way. In fact, they emphasize again and again that the point is to USE the information to REALLY take your "Dream Trip" soon! The Facebook group is the best I've ever experienced with an online course. Stephanie and Chris are remarkably present, responsive, understanding, and generous with their knowledge and experience. I highly recommend this course.