A Beginner’s Guide To Building Air Miles And Getting Free Upgrades

So you’ve decided to be a globe-trotting vagabond. Congratulations! A world of adventure awaits you! Two words of advice: Be smart. Spend money well and reap the benefits of the huge systems that are already set up to help you travel further, longer, and more comfortably.

We’d like this guide to be a jumping off point for someone who is just learning about air miles. We’re not talking about “points churning” just yet, but these are salient tips and links that are sure to help out the newbie. Some of these tips require investment and careful planning. Others are a bit more personal. Either way, these are the steps you can take to actually get reward seats, free car rentals, first class upgrades, and posh hotel rooms.


It’s 2017 and we should all have cash back reward cards. But cash back is easily spent on trips to the movies or nights out on the town. Easy money is easily spent, as they say.

Think about getting a credit card that has a travel, hotel, or airline rewards system built in. Many offer a substantial block of miles simply by signing up and spending a certain amount of money within the first month, quarter, or year. Some of them offer enough miles to rent a car or book a hotel room with their sign up bonuses alone. Here’s a list of some of the better credit cards on offer with all the pertinent details on reward and cash benefits.

Find one that suits you and your travel, banking, and financial situation and run with it. It’s best to look at these cards as your cash flow. Budget your grocery and entertainment expenses for the month, use the card for those buys, and then pay it off every month. You’ll be building credit and travel rewards at the same time.




If you already have a credit card linked to a specific airline, stick with it. If you’re using, say, Alaska Airlines’ Visa, then fly Alaska every time you can — even when it’s a little extra. Airlines and hotels reward loyalty above all else in the travel game.

Sign up for Hilton Honors or Marriott Rewards and start staying at those groups’ hotels. These hotel groups are massive with options ranging from affordable to pricey to luxurious.

All the major airlines have alliances these days. The three main alliances are Oneworld, SkyTeam, and Star Alliance. This gives you a broader range of options when you’re flying. Check the alliance of your favorite airline and search for flights within those groups exclusively. You don’t have to do anything extra to do this. Check out this screen grab from Kayak. Look center left. You can easily search for flights that fall into you mileage plan with a single click.

The more you fly with a single airline or its alliance and stay at the same hotels, the more that company will know who you are. And you’ll be treated well. This literally equates to upgrades, pre-sales, cash back, and free seats, rooms, and car rentals.



Okay, we’re going to contradict ourselves a little because the world is full of contradictions. Work every angle. Don’t be afraid to sign up for all the loyalty programs you can — especially the main airline alliances. It’s smart to have at least one reward program per air alliance. That way if you can’t fly your regular airline, or someone else books you business travel, something unforeseen happens, or you just want to try a new airline, you’ll be collecting miles and rewards.

Loyalty is good, but don’t let blind loyalty get in the way of your collecting benefits from other corporations when the moment strikes.



Look up prices on aggregators like Expedia.com or Booking.com then go to the airline or hotel’s actual web page to book. The carriers and hotels know that they’re getting all the payment and not giving a third party a cut. They appreciate this immensely.

Sites like Kayak.com give you this option when searching for flights. Next to the “View Deal” button is a little downward facing arrow. Click on it and options will come up for you to buy that ticket from other vendors and often the airline directly.



If you aren’t an affable person in the first place, there’s little to no chance you’re getting anything for free. Especially without a well used rewards/loyalty program.

Seriously. This whole section could be titled, “Hey, do you want free stuff and to be treated well? Then don’t be a piece of shit.” A smile will get you a long way. Don’t act entitled to anything you haven’t already paid for or that your reward status doesn’t guarantee you. Be chill when you’re in line. Be cool when you’re at the desk. And be nice on the plane and to the hotel to staff. The service industry is staffed by working human beings who have to deal with other human beings nonstop during their work day. If you are kind, people will want to hook you up.


This works. Dress like a boss and you’ll be treated like one. No one is getting upgraded to first class if they’re in yoga pants or cargo shorts. Sure, you can pay for those seats in full and rock those tights. But don’t expect an airline or hotel to reward you for not dressing like someone who belongs in their high-end cabins, lounges, or suites. This may seem classist and uncomfortable, but thems the breaks. And it works. Dress in smart business attire and you will be treated better and may even get a surprise upgrade or two.


Can you pack everything you need for two weeks in an appropriately-sized carry on bag? Like this The North Face bag for instance? It’s sized exactly to fit in the overhead bins according to every airline’s specs. This is important. If you’re fishing for an upgrade, the desk clerk will 100 percent check to see if they have to move your bags and how much shit you’re going to be dragging onto the plane. If you don’t have a bag to move under the plane and you’re not schlepping a computer bag, food bag, duty-free bag, and odd-sized carry-on, you have a much better chance of getting that upgrade.

Travel sparsely and tidily. No one is getting into a business class or first class cabin with half their closet, desk, and fridge hanging out of three or four plastic bags.



If there’s a call for people to give up their seats, jump up and take it. But know what you’re getting into and what you can negotiate. First, it’ll look good on your loyalty program that were able to be flexible. Second, ask for a hotel room, meal voucher, seat upgrade, and ticket voucher for your next flight. Airlines are allowed to give you up to $10,000 in some cases for getting bumped. European airlines will put you up in a hotel with meals and transport if there is an overnight delay — and often they’ll send coupons for future flight purchases if you ask.

This requires a bit of research on your part. So read passenger’s rights sections of airlines and know ahead of time what to expect if something unforeseen happens. Don’t be the person that’s clueless and pissed off. Be the person that is calm and ready.


Hotels work on tips. If you want to play the game, you have to pony up. Slide a $20 under your reservation print out or passport when you check in and ask if there are any upgrades today. Slip the concierge a $20 and you’ll assuredly get better information about where you’re staying, and maybe even a friendly eye on the reservations system in case a better room comes up.

There’s also the matter of being cool about this and doing it with a smile. Don’t get pissy if there aren’t upgrades. That’s not their fault. It’s hit and miss. The calmer and friendlier you are, the bigger chance that your phone will ring when a cancellation does come in.



When you get on the plane, be nice to the flight attendants. The head flight attendant (purser) is the person who greets you at the door. Don’t tip this person with cash, but a Toblerone bar or another sealed confection might go over well. Say hello, be nice, stay outta the way. This will pay off. And if you fly the same route a lot, keep this relationship up with the same crew. Then it’ll really pay off.

If the purser comes up and asks you to change your seat to accommodate a family, be gracious and you’ll be rewarded. Maybe not with an upgrade, but with a nice cold beer or glass of wine or a gin and tonic. If it’s a flight and crew who knows you well or one that you’ve sweetened up a little, then maybe they’ll just walk you up to a business class seat.


Sometimes you have to go all in and just ask. Dress well, put a smile on your face, and ask for an upgrade when you check in to your flight or hotel. Sometimes they’ll say no. Sometimes they’ll be generous and put you on standby. And sometimes you’ll get lucky and they’ll reward you with a better seat or room. The less you expect, the more satisfying the rewards will be when you reap them.

And if you’re not into asking for free shit, then sign up for a rewards system now. Start traveling and spending cash to build your benefits. And then reap those rewards on your next trip!