This year, Erik and I each had a Companion Pass for Southwest Airlines. Now that most of our travel is scheduled through the end of 2022, I can assess how much value we got out of these passes this year.
I travel more than Erik, since he’s stuck going to his job and I work for myself. However, he tends to take more expensive flights than me, for the same reason. I was surprised when I added up our flights and found that we both got about the same dollar amount of free tickets for our companions in 2022: $1,700 each, or $3,400 for our family. That’s very similar to the $3,300 we saved last year. We are flying more this year, but getting better deals on flights, which surprised me since in general flights got more expensive in 2022.
I’m kind of jealous of you guys right now. Because I’ve been spending my booty off for the past few years to qualify for Southwest Companion passes, and now Southwest and Chase are just going to hand one to you.
So you noticed other people are getting free trips by using their credit cards. You want in on that. Of course you do! But where to start?
Friends regularly ask me, “How do I get started earning miles for free trips?” or “What credit card should I get if I want to travel free like you do?” I usually ask them a few questions that help them narrow down their choses, based on their preferred destinations and spending habits. But you could do this yourself, by answering these questions.
What Kind of Trips Do You Have in Mind? If you want to fly to visit relatives and will always have a place to stay, or if you mainly stay in AirBnBs, focus on an airline card (and we’ll get into which airline below). If your trips typically involve both flights and hotels, or if you aren’t sure what you’ll do, consider an all-purpose travel card like Chase Sapphire. If you’re considering road tripping but want to stay in hotels, a hotel card may be perfect for you.
How often and how far will you travel? If you want to plan just one trip in the next year, you may be just fine with an entry or mid-level rewards card. Those typically have lower annual fees, like $69 or $99 per year. But if you’ll fly 10 times in the next year, or are planning one or more multi-destination international journey, you might want to take a look at a premium rewards card like Chase Sapphire Reserve ($550 annual fee) or American Express Platinum ($695). Those annual fees might sound insane, but the benefits for frequent and international travelers are often worth more than what you paid. For instance, AmEx Platinum offers more than $1,000 worth of credits at partners, plus access to hundreds of airport lounges, where you can usually get a free meal and drink. The Chase card covers the cost of Global Entry or TSA Precheck every four years, meaning less waiting when you travel.
What airports will you use? If you’ve settled on an airline card, choose one that has a good choice of flights to from your home airport to your preferred destination. For instance, I live near the Oakland airport and fly the most to the Milwaukee/Chicago area. Because Southwest has a decent number of flights between those cities, we’ve focused our airline miles strategy on Southwest. But since Southwest flies to only a few international destinations, I wouldn’t use Southwest cards if I was trying to save for a trip to Europe. I’d probably go for American or United.
Who will you travel with? If you’ll typically fly with someone else, it’s worth looking into earning a Southwest Companion Pass. You get one by earning 125,000 miles in a calendar year. My husband and I have both earned these passes for the past couple of years, mostly by using our Southwest Visa cards.
How much will you charge each month? This actually isn’t something I ask my friends, because it’s none of my business. But it’s important to keep in mind, especially when you’re looking at signup bonuses. Most new card bonuses require you to spend a set amount in the first few months in order to earn the bonus. For instance, if the offer requires you to spend $3,000 a month for the first three months, but your typical household budget is only $1,500 a month, you’re looking a temporary spending increase or you might fail to get the bonus. Now, if you’ve been saving up for a few big ticket items and you time them right, that might still work out. But of course you don’t want to run up credit card debt and end up paying a lot of interest, just trying to earn miles. How much you usually charge is also relevant for the Southwest Companion Pass. Our household of five happens to charge quite a bit most months. In addition, we’ve had some saved-for big ticket items that we were able to charge, like materials for a major renovation, and a new roof. But if you don’t typically spend enough to get anywhere close to earning 125,000 miles in a year, just don’t focus on spending your way to a Companion Fare. It’s not the right strategy for you.
What cards have you already gotten? If you have already started dabbling in the miles game, you may have applied for a few new credit cards in the past couple of years. This is important to keep track of, because some brands don’t want customers who have taken out a lot of cards recently. Chase is the company most well known for limiting accounts. They have something known as the 5/24 rule, which means that if you have opened five or more new accounts in the past 24 months, you probably won’t get approved for many Chase cards. Here’s a strategy you can use to work with Chase’s rule: If you’re just getting started, consider Chase’s best cards before other candidates. This is because you have a good chance of getting approved at this point, before you start taking out new credit accounts. So if you want one of Chase’s Southwest or United cards, or a Chase Sapphire, go for that before you get any other cards. If you’ve already taken out five new accounts in the past two years, you can just forget about the major Chase travel cards and focus on other brands, or you can take a break until you qualify again.
What points do you already have? If you’ve been staying at Marriott properties for years and have some points and status at that chain, it may make sense for you to get a Marriott branded credit card to build on what you’ve already got going. Also, if you have a few points from a brand but haven’t been able to redeem them because they’re not quite enough, getting a credit card could help boost you over the top.
Do you have a business? Keep in mind that there are business versions of most of the major travel cards. If you have a small business — especially if it has its own employer ID — you can rack up some extra signup bonuses by getting the business version of the card in addition to the consumer version. You can do this even if your business doesn’t have a lot of regular expenses — as long as you have enough business spending to hit the minimum initial spend to qualify for the bonus.
What card is paying a good bonus right now? The signup bonus can be a major part of the rewards you reap from a credit card. In fact, I have applied for many cards, collected the signup bonus, and then canceled. If there are several cards that would meet your needs, the current signup bonus may determine which one is best to start with. You can see regularly updated lists of the best current offers on a number of sites, including One Mile at a Time.
What cards can your friends get signup bonuses for? If you’ve answered all the above questions and still aren’t sure what card to get, ask a friend who’s into miles and points if they have any “refer a friend” offers at the moment. Your friend could get a bunch of miles for signing you up, and sometimes these offers give the new cardholder a better deal than they could get without the referral.
How did I, a sort-of credit cards expert, come to find out only now that I could get a free Shipt subscription with my Visa card, four months after it was announced?
Let me set the scene for you. I am in frigid Wisconsin, having returned here just two weeks after my last visit. Family funeral, alas. My family is making due as best they can without all that sweet work-at-home-mom value I usually add.
I absolutely love the ocean. And yet, staying at a luxurious oceanfront spa hotel was a bit of a departure for me. Most of my trips to the beach are simply day trips with the dogs and kids. Sometimes we go camping near the ocean. And any trip at all for our family is more likely to be a rental house or home exchange than a hotel stay.
But one of my best friends, who lives in Florida, loves One Ocean Resort & Spa, and has wanted to share it for years. So when we decided that Thanksgiving weekend would be a great time for a girls’ getaway, we quickly agreed on One Ocean as the destination. My friend made sure we got a room with a balcony, because what is staying right on the beach all about? Obviously, staring out at the surf and sleeping with the doors open.
Since completing earning Southwest Companion Passes for Erik and me a couple months ago, I’ve been in a bit of a holding pattern, trying to push off major credit card spending until 2022, when I could start fresh on earning those 2023 Companion Passes.
But today something hit me as I was riding my bike with my son.
Another post I found in my drafts folder, from our trip to Australia way back in September 2016.
Our last full day in Australia was a little challenging to plan because we’d be traveling between Ettalong Beach and the Westin in Sydney, and I thought it would be nice to stop partway to check out the Hawkesbury River. Although the trip only takes about an hour and a half by train, and there are plenty of trains throughout the day, we’d have all our luggage along with us.
As of the day before, I hadn’t lined anything up.
But a last-minute flurry of emails secured us the last six seats on the Riverboat Postman on the Hawkesbury.
There are airborn events I’ve heard about that I dream of experiencing, like getting bumped to First Class. Then there are Mile High Clubs that I never wanted to join — not just the original MHC (ew), but the Oxygen Masks Actually Descend Club, for instance, or the Turbulence Caused a Toilet Tsunami Club. (OK I’ve never actually heard of that but turbulence can get really bad.)
Or, the Medical Emergency Landing Club. Never wanted to belong. Joined it this week.
When I took the great Don George‘s writing class, one of the best pieces of advice he gave seems like the most obvious, but I’m amazed at how often I fail to follow it: Take copious notes!
When you’re having an amazing travel experience, it’s easy to think, “I could never forget this piazza beneath the bluest sky or these porpoises leaping from the bay.” Oh, couldn’t you?
I recently found a journal that I had forgotten writing, about an experience that was less joyous than the above, but definitely memorable. It was from our September 2001 trip to China, including my contemporary account of the events of 9/11. Since I recently wrote about those same events from memory, today I’m sitting down to compare how my memory stood up to what I wrote back then.