How to be a Cheapskate Jetsetter

Chris Ronzio

Since starting SundayBucket last June, my wife and I have traveled to Seattle, Portland, San Francisco, Napa, Boston, New Jersey, Las Vegas, Los Angeles, and Denver, checking off plenty of Bucket Slips along the way. And we’ve spent less than $1,000 doing it.

The trick is a combination of brand loyalty, smart spending, and timely booking. If you want to, you can travel for almost free too! Here’s how:

First, pick a hotel chain and an airline that you like. To decide, consider the brand’s locations and destinations of service, their rewards programs, and their membership perks. For cheap domestic travel, Southwest Airlines and JetBlue are usually safe bets, and Hyatt, Marriott, Starwood, and Hilton are all great hotel choices. We chose Southwest, for its extended service in and out of Phoenix, and Hyatt, for their range of properties and their Gold Passport rewards program.

Signing up for rewards programs are free, so you might as well establish an account with every airline and hotel chain that you’ve ever used or anticipate using. You can usually find signup bonuses for 250-1000 points/miles with new account signups, which gets you off to a great start.

If you have decent credit, the best way to bulk up your account is to sign up for their credit cards. Credit card signups can get you between 25,000 and 50,000 points (sometimes more!). Southwest in particular runs a promotion each year for 50,000 points, which they advertise as 2 round trip flights. In reality, if you use the points for short, regional flights, you can often squeeze 3, 4 or 5 round trips out of them. Most travel-related credit cards also award free nights or miles and instant premium status in exchange for the card’s annual fee.

Using the cards, there are opportunities for other points bonuses, like shopping or dining at partner companies, or booking rental cars. But, you typically get the most benefit by using the card to spend money with the company that the card represents (i.e using the Southwest Visa to book Southwest flights).

The credit card route is not necessary, but if you’re using a cash-back card, a debit card, or (gasp) checks for your everyday and business purchases, you are flushing money down the toilet. So, pick a credit card that rewards you for money you already spend, and stick to it!

Without a card, you can still get bonuses. Completing surveys, linking your social media accounts to travel reward programs, and registering with partner companies are easy ways to accrue a few hundred dollars in free travel each year. The best way I’ve found to keep up with these deals is a subscription to, which starts at $15/mo (disclaimer: the above referral link helps me earn points, but I wouldn’t recommend something I didn’t use myself).

Traveling is an easy way to rack up points, but watch for promotions to maximize your earnings. Each spring, Hyatt is known to give 5,000 -10,000 point bonuses after every few stays, so a business trip could easily rack up a few nights in leisure lodging. We’ve even booked cheap stays at local hotels for $70 because they got us a point bonus worth $250 in future stays.

Finally, book smart. Subscribe to newsletters with your favorite airline and hotel chain so that you hear about each sale (like Southwest’s 40% off on Black Friday that got us to Vegas for $78). Southwest has a calendar for searching fares when your dates are flexible, so if you can plan your trips around the airline’s availability, you can be sure to get the best deals.

Travel hacking is a hobby that takes some time, but for us, it’s worth it!

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Showing 5 comments
  • Ken Mosesian

    Chris, sound advice all around. I would add that with many airlines, as you accumulate actual miles flown and pass specific milestones, a variety of “handcuffs” are placed on you by the airlines, designed to keep you loyal by making leaving a loosing proposition. Delta, my airline of choice, has specific benefits at 25,000, 50,000, 75,000, and 125,000 miles flown. They include priority security screening, discounted or free access to airport lounges, and mileage bonuses, which can really add up. For example, at the Diamond (125,000) level, you receive a 125% mileage bonus for every mile flown, more than doubling the number of miles you have to redeem for upgrades and free flights, relative to the number of miles flown. I also regularly check in on Flyer Talk and Mile Point. Great post!

    • Chris Ronzio
      Chris Ronzio

      Great additions, thanks Ken! I forgot to mention the airport lounges, which are a definite perk for more frequent travelers. For reference, here are the links Ken mentioned:;

pingbacks / trackbacks
  • […] A one-day getaway is simple… Book a round trip flight to a nearby destination for a quick change of scenery, without taking time off! A couple weeks ago, Southwest Airlines had a 40% off special, so we made our move and booked two flights to Las Vegas, at a total cost of $78 (tips on cheap travel here). […]

  • […] visit Wine Country without stopping at a few tasting rooms. If you have a Visa Signature Card (like the Southwest/Hyatt cards we use to fuel our traveling), you qualify for free tastings, discounts, or two-for-one tastings at dozens of Sonoma wineries. […]

  • […] frequently is another major benefit of the decision. Oh, and how could I forget the points! I’ve traveled around the world on points from my business purchases, so it’s only fair that I help my clients do the same. So, […]

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