Travel Hacking Deep Dive: The 2-Card System That's Saved Me ~$100K

Hope this post finds you in an okay place! And if not, it might just help you book the trip you need to take — for free — so let's get into it.

🔥 Oil prices have been rising, along with a few other questionable aspects of the economy, and whew is that doing a doozy on travel. Airfare is up over 20% from last year, hotels are nickel-and-diming us with resort fees, and a long weekend somehow costs what a whole week used to. Love that for us.

After I shared on IG stories that I travel-hacked my way into the Plaza Hotel this December (my sis and I are taking a bucket-list trip and reliving all of our '90s-kid Home Alone pipe dreams), my inbox basically turned into a travel-hacking help desk. Y'all wanted the deeper version. The "okay, but how do you accumulate points without spending millions of dollars," the "which Southwest tier do I even pick," the "is the fancy card EVER worth it" version. So I blocked off an afternoon and wrote this out like I was your grandmother documenting secret recipes for generations to come.

This is the exact two-card system we run. The cards, the strategy, the real math, and the honest "here's when I'd skip it" notes. Pour a coffee, sit down, and read the whole thing.

🚨 One non-negotiable before we go a single inch further: this ONLY works if you pay your balance in full every month. Carrying a balance at 20%+ erases every point you earn and then some. The $600 in points you racked up while paying $800 in interest? Not it. Get the budget and the habits solid first (my free money tracker is a great place to start), THEN come beat them at their own game. Deal? Deal.

First, the strategy (the part nobody explains well)

Here's the thing almost no one breaks down for you: the two cards I run do two completely different jobs even though they're both travel cards — and that's exactly why I carry both.

1️⃣ The co-branded card (my Southwest card) is tied to ONE airline. The points live in Southwest's world and nowhere else. In exchange for that loyalty, the airline hands you stuff you genuinely cannot get anywhere else: a free checked bag, better boarding priority, and the holy grail — the Companion Pass. If you're a loyal Southwest flier, this card basically pays you to keep doing what you were already doing.

2️⃣ The flexible card (my Chase Sapphire) earns points that aren't locked to anybody. You can move them to a dozen different airlines and hotels, or just book straight through Chase. We use our points here to cover lodging when we travel. Decide you hate the airline you've been loyal to for years? No biggie with this card. Need to book with a hotel chain you don't normally stay at for your cousin's wedding? These points have your back (I'll show you how to transfer them to hotel & airline partners in a minute!).

So here's why we run them together (my husband and I EACH have both): the Southwest card racks up the everyday perks where we fly most, and the Sapphire builds a flexible stash we can throw at literally anything else. That combo is how we've saved roughly $100K on travel over the years. No spreadsheets from hell. No opening 14 cards a year. Two cards, used responsibly. That's it.

Card 1: The Chase Sapphire Preferred (our everyday workhorse)

This is the card we run *almost* everything through, and it just got a refresh in June that made earning points even easier. The annual fee is still only $95 (one new catch detailed below).

🚨 Right now it's carrying a 100,000-point welcome bonus after $5,000 in spend in your first 3 months. That's only the THIRD time in this card's 17-year history it's hit 100K (yes, I looked this up). If travel is anywhere on your radar this year, this is your window. Also, low key appreciate you using my link to apply if you find this information helpful. At no additional cost to you, I get some points for referring ya.

What it earns (built for real-life spending):

• 5x points on travel booked through Chase Travel
• 3x points on dining, including takeout + delivery
• 3x points on select streaming and online groceries
• 3x points on gas and EV charging (new in the refresh!)
• 3x points on vacation home rentals (also new)
• 2x on all other travel, 1x on everything else

We run every restaurant meal and online grocery order through this card, and now with the gas addition we'll do that too. That 3x adds up shockingly fast.

The perks that quietly cover the fee:

• A $100 Chase Travel hotel credit every anniversary (just doubled from $50)
• Complimentary DoorDash DashPass ($0 delivery fees, lower service fees, monthly credits)
• Up to $120 toward Global Entry, TSA PreCheck, or NEXUS every 4 years (PreCheck or Clear runs ~$80 — so there ya go!)
• A free year of Apple TV when you activate by Dec 31, 2026
• Real travel protection: trip cancellation/interruption up to $10K per traveler, lost luggage up to $3K, rental car collision coverage, and travel + emergency assistance. No haggling after a travel nightmare — you just call the number on the back of your card.

Between the hotel credit, the DashPass value, and the welcome bonus, you come out ahead in year one before you've touched a single point. THAT'S what makes the $95 a no-brainer for me.

Now here's where the real magic lives: transfer partners. Your points move 1:1 to actual airline and hotel programs — United, Southwest, JetBlue, Air Canada Aeroplan, British Airways, Virgin Atlantic, Marriott, IHG, and my longtime MVP, World of Hyatt. Hyatt points stretch absurdly far, and Hyatt owns so many resort properties (many that don't even carry the Hyatt name) that it's insane. I've transferred Chase points to Hyatt and stayed at a 5-star resort priced over $1,000 a night — all on points I earned just by spending like a normal person with a budget.

One honest heads-up, because I'll always give you the facts straight, and this is a slight blow in recent news: Chase just changed the Hyatt transfer ratio on the Preferred. As of June 15, 2026, NEW Preferred cardholders transfer to Hyatt at 4:3 instead of 1:1 (so 40,000 Chase points become 30,000 Hyatt points). This ONLY applies to Hyatt transfers, since Hyatt points are so lucrative — all other travel partners (Marriott, United, etc.) still transfer 1:1. If you got the card before June 15, you keep 1:1 Hyatt transfers through October 1, 2026. The Sapphire Reserve and Reserve for Business still transfer to Hyatt at the full 1:1. So if Hyatt is your whole entire strategy, that's a real check in the Reserve's column. More on that math next.

Preferred vs. Reserve: when does the $795 card actually make sense?

If you aren't aware, the Chase Sapphire card has two "levels." For most people, the Preferred is the sweet spot. Full stop. This is the card we've carried. But the Reserve is running a RECORD 150,000-point welcome bonus right now, and it keeps that 1:1 Hyatt transfer, so let's run the real numbers together.

Okay, the fee-offset math, no fluff: that $795 fee looks downright scary until you actually line up the credits. The easy, no-gymnastics ones are the $300 travel credit (applies to basically any travel charge automatically) and up to $500 in hotel credits through The Edit if you book hotels at all. Those two alone basically wipe out the fee. Stack the dining, Apple, and Peloton credits IF you'd actually use them, and the card can pay for itself a few times over.

My honest filter: a credit only counts if it's replacing money you were ALREADY spending. A $120 Peloton credit is not "savings" if there's no Peloton in your house. So I'd only reach for the Reserve if you (1) fly enough to actually use the lounges (I've heard they're luxury), (2) book hotels often enough to burn through the travel + Edit credits, or (3) live and die by Hyatt and want that 1:1 transfer protected. If that's not you? Keep the Preferred and pocket the $700 difference.

Card 2: The Southwest Card (my free-flight machine)

If the Sapphire is my flexible card, Southwest is my loyalty card. Right now all three personal versions are running one of the lower signup offers, so if you're eyeing this card, I'd recco waiting for a better sign on bonus. 

👉🏻 The part people don't clock until they're standing at the bag drop getting hit with fees: when Southwest ended free bags for everyone back in May 2025, cardholders got protected. Hold ANY Southwest card and your first checked bag is still free — for YOU and up to 8 people on the same reservation. You also get earlier boarding and better seat selection under the new assigned-seat system (which, real talk, I flew recently and actually preferred — no more cattle-call shuffle praying for a decent seat).

Here's the current lineup, side by side (the Southwest card has 3 "levels"):

The tradeoff, plain and simple: all three give you the headliner perk (free bag + boarding). The fee jumps buy you faster earning on Southwest, bigger anniversary points, and day-of-travel perks like better seats and free legroom upgrades. We hold the Priority card for our personal cards — you'll select which card you want when you apply.

Let's do the math on stepping up a tier. Going from Plus ($99) to Priority ($229) costs you $130 more a year. The Priority hands back 7,500 anniversary points (worth roughly $90 toward flights) PLUS higher earning on Southwest PLUS free extra-legroom upgrades. So if you fly Southwest more than a couple times a year and care about a decent seat, that $130 comes back to you fast. Fly once or twice a year and just want the free bag? The Plus does the job and saves you the $130. Pick the tier that matches how often you ACTUALLY fly Southwest — you can always upgrade your card to the next tier down the road.

Now the Companion Pass, because THIS is the real prize. It's the perk where one person you choose flies with you for (basically) free, all year long. You need 135,000 qualifying points in a calendar year, and every single point from your card counts toward it, including the welcome bonus. Cardholders also get a 10,000-point boost each year, which drops your real target to 125,000. So a big welcome bonus right now plus your normal everyday spending can put a Companion Pass within reach way faster than you'd think. Nothing else in the airline world touches it. (This is how I'm flying my sister to NYC with me in December.)

Quick honesty note: these current Southwest offers are points-only — they don't come with a Companion Pass attached. That said, the welcome bonus you earn right now counts toward your qualifying points for the Companion Pass. If earning the Pass through a welcome offer is your main goal, you may want to watch for a Companion Pass promo to come back around (TBD, zero insight there). If you just want to stack points and fly? Now's a strong time.

Now watch them work together (here's a real year for me)

This is the whole reason I carry both. Picture a regular year of my life:

• Southwest flights + everyday spending (outside of eating out + groceries, which we put on the Sapphire) toward the Companion Pass go on my Southwest card. Free bag for me and whoever I'm dragging along, early boarding, and points stacking toward flying others for free.
• Dining, groceries, and any large one-time expenses that accept credit cards go on my Sapphire Preferred, quietly earning flexible points the whole time.
• Need a HOTEL? I transfer Sapphire points to a hotel partner and book a room that would've cost four figures in cash.
• Flying somewhere Southwest doesn't go? I transfer Sapphire points to United or another partner and I'm covered.

The Southwest card handles the flights and the bags where I'm loyal. The Sapphire handles the hotels and the wildcard trips everywhere else. Two cards, two jobs, zero overlap. THAT'S the system, and it runs on autopilot once it's set up.

How to actually transfer points to partners (the part that scares people off)

I walked through the philosophy of all this in my old, old, OLD blog post, How to Travel for Free or on a Bite-Sized Budget, and it's STILL one of the most-read things I've ever written. Here's the updated, click-by-click version for the Sapphire:

1. Log into your Chase account and open the Ultimate Rewards / "Rewards" hub for your Sapphire card.
2. Find "Transfer to travel partners." You'll see the whole list of airlines and hotels (United, Southwest, Hyatt, Marriott, all of 'em).
3. Pick your partner and link your loyalty account. First time, you punch in your frequent-flyer or hotel number once and it saves for next time.
4. Choose how many points to move. Transfers are 1:1 for almost every partner (Hyatt's the 4:3 exception on the Preferred now). Points usually land within minutes to a couple days.
5. Book on the PARTNER'S site, not Chase. This is the step everybody skips. Once your points are sitting in Hyatt's account, you log into Hyatt and book the award night THERE. That's where the outsized value actually lives.

The golden rule I'll repeat till I'm blue in the face: only transfer when you've got a specific booking in mind AND you've confirmed the award is available. These transfers are a one-way street, so you don't want points stranded in some airline program you never use. Confirm the seat or the room first, THEN move the points.

Savvy way to double your household points

If you share finances with a partner, you're leaving SO many points on the table by playing this as a one-person game. A few of my favorite moves:

• Two people, two welcome bonuses. You and your spouse each open the same card (at different times) and each earn the full welcome bonus. That's potentially 200,000 Sapphire points in a year on the Preferred alone, from spending you were doing anyway. Hello.
• Pool your Chase points. Chase lets you move Ultimate Rewards points to another cardholder in the same household for free. So one of you can hold the Reserve for that 1:1 Hyatt transfer + better redemption rate, and the other's points flow right over to use it. The higher-tier card basically upgrades the WHOLE household's points.
• Stack toward ONE Companion Pass. Pick who's holding the Pass for the household and funnel the Southwest earning under that person. Once they've got it, the OTHER adult becomes the named companion and flies along all year. (Yes, this is exactly what couples do. It's genius.)
• Use authorized users on purpose. Adding your partner as an authorized user can speed up spend toward a welcome bonus. Just confirm the points + any bonus terms before you bank on it.

Play this as a household. The math gets a LOT more fun when there are two of you.

What I'm eyeing next: the Chase Sapphire Reserve for Business

A little personal note, since plenty of you are business owners too. For years I've run my business spending through the Southwest Performance Business card, and it's been great for racking up Southwest points and protecting those flyer perks. But I keep smacking into the same ceiling: those points ONLY work for Southwest.

So I'm seriously eyeing the Chase Sapphire Reserve for Business for the flexibility, and the welcome bonus right now is genuinely massive.

• Welcome bonus: 200,000 points after $30,000 in spend in the first 6 months (the kicker). Worth roughly $4,100 by current valuations.
• Annual fee: $795
• Earning: 8x on Chase Travel, 4x on flights + hotels booked direct, 3x on social media and search advertising
• Business credits: up to $300 travel, up to $500 The Edit, up to $200 Google Workspace, up to $400 ZipRecruiter, up to $120 Lyft annually
• The flexibility I'm after: it transfers to all the same partners AND keeps the 1:1 Hyatt ratio the personal Preferred just lost

My honest read: that $30,000 spend requirement is no joke, so this only makes sense if your business genuinely runs that much through a card in six months. For me, the whole appeal is getting OUT of airline-locked Southwest business points and into flexible points I can send anywhere, while the credits + the 1:1 Hyatt transfer help justify the $795. I'm running my own numbers before I pull the trigger...and you KNOW I'll report back honestly either way.

The usual transparency note

Same as always: I earn a small referral bonus if you sign up through my links. I share these because I actually use these cards and they've saved me real money. If they're helpful to you too, the links are a no-cost way to support the free content. And the rule never changes: pay in full, every month, or none of this works. Love ya, mean it.

Xx — Mal ✈️