Travel hacking rules we break (and why)

If you’ve done your research, you’ve likely found that there are dozens (if not more) of travel hacking rules to ensure you get the maximum value for your efforts. And, if you follow these “rules”, there’s a good chance you will find yourself earning hundreds of thousands of points. And, in turn, redeeming those points for trips that everyone is envious of on Instagram.

We wouldn’t say we’re experts. We are, however, somewhat experienced as our first big points redemption took us to four European countries all the way back in 2018.

Despite this, there are common travel hacking rules we’re okay with breaking. In fact, we break them most of the time we’re accruing and / or redeeming points.

Let’s break it down.

Airline Loyalty

We are 99% loyal to United Airlines, particularly when flying domestically. Chicago’s O’Hare airport is a United hub that typically gives us the most amount of options for flights. In addition, we each have a United Explorer credit card that gets us priority boarding and free checked bags.

When we have redeemed points and miles this year, there have been a few instances were we did not fly United. First, when we flew between Oahu and the Big Island (Southwest) and then Big Island and Maui (Hawaiian Airlines). We also flew Austrian Airlines to Vienna (but they are a Star Alliance partner with United). Similarly, we flew TAP to Lisbon and from Lisbon to Barcelona. Our final flight of the year was on Iberia to get from Madrid back to Chicago.

You will likely have more options if you don’t stick with one airline; however, P2 has Gold status which gets us free upgrades and faster accruals on United. For us, this is worth it.

Hotel Loyalty

Echoing the above, you will have more options for hotels if you aren’t loyal to one chain. It’s well known that Hyatts have the best redemptions as one of the exclusive transfer partners from Chase. P2 has a Marriott Bonvoy card, which has helped us get Titanium status and earn free nights faster.

Any time we’re paying for a hotel, we’re staying at a Marriott and accruing at a minimum 6 points per dollar per Marriott stay. We also have redeemed several weeks worth of nights with Marriott. Read more here on why we prefer staying at Marriott.

We have stayed at Hyatts twice this year (Honolulu and Santa Barbara) and Hiltons twice as well (Hilo and West Virginia). All four of these stays were using points. The Hilton points had been accrued from previous stays when P1 worked at an employer that preferred Hilton for work travel. We transferred Chase points to cover those Hyatt stays for the tremendous value.

Opening new credit cards

Many travel hackers like to open new credit cards every 30-90 days to maximize their sign-up bonuses. While we do open new credit cards when there is an offer we like that fits with our spending, we don’t open new cards that frequently.

We like the cards we have – we each have one card (Freedom Unlimited) that gets a minimum of 1.5x points on every purchase. For the categories we spend more on (dining, groceries, etc.), we have cards that earn at least 3x or 4x points.

Bank diversification

If you read up on the best cards to open, you’ll find a variety of providers – Chase, Capital One, American Express, etc. The vast majority of our cards are with Chase. We each have one American Express Gold card that we use for groceries (4x), but P1 is considering downgrading hers because we don’t receive the full benefits to make it worth the $250 annual fee.

Chase, however, is where we currently hold over 400,000 points and counting. We each have several cards that we use on a regular basis to continue adding to our total. Chase transfers to our preferred travel providers and gives us flexibility when needed.

Cents per point

For some travel hackers, cents per point is make or break. Basically this helps people learn if they’re getting a good value for the points they’ve earned when redeeming those points. If you’re curious, the Points Guy has an article on calculating redemption value.

This can be a good metric for some – for us, however, free travel is free travel, regardless of the cents per point. There have been times after we’ve booked where I’ve looked up the cents per point for the redemption out of curiosity. And, in some cases, our cents per point was less than the value of that point. We still went on a wonderful trip somewhere that we couldn’t have afforded otherwise, so we still count it as a win.

Travel planning

Being flexible is a great way to maximize your travel hacking. In fact, one of the travel hacking “rules” a lot of people follow is to let the deal guide the destination rather than the other way around.

We are flexible to an extent – we know places we want to go and in many cases are willing to wait until there’s a good value of points and miles to visit. There are certain times, however, that we pick a place and figure out how to use points and miles to get there.

Here’s how it looked for us – we decided to go to Hawaii in January 2023. We each had slower periods at work and neither of us had been to any of the islands. Once we had decided the destination, we figured out how to use points and miles to cover the flights from Chicago to Hawaii, Hawaii home to Chicago, and hotels for all 8 nights we were in Hawaii.

Summary

If you research travel hacking, you’ll find an abundance of advice on how to maximize your earnings and redemption. And there is a lot of great advice out there. We believe, however, the best way to travel hack is the way that works for you.