By Scott Mayerowitz
December 24, 2013

Frequent-flier miles and hotel points are perks of life on the road—currencies that are supposed to make it all worthwhile. A string of stays at cookie-cutter convention hotels and side-of-the-road motels adds up to a free tropical family vacation at a jaw-dropping resort.

That’s the promise, at least.

Most frequent travelers know the ins and outs of these programs well. Some people even become obsessed with their mileage balance. But even the best pro can learn something new. Here are my favorite tips for some of the more obscure ways to earn and redeem miles. Feel free to add your own in the comments section below.

The right credit card. Want to earn American Airlines or Delta Air Lines miles through credit card spending? Don’t get the airlines’ branded credit cards, which offer one mile for each dollar spent. Instead, try the Starwood Preferred Guest American Express. You still earn one Starwood point per dollar spent. But the real value comes during redemption. For every 20,000 Starwood points you convert to an airline program, you get 5,000 extra miles, which is essentially 1.25 American or Delta miles per dollar spent. The only advantage to the American and Delta credit cards is that they offer a free checked bag and priority boarding. But those benefits are moot if you already have elite status on the carriers.

Miles for dining. Just about every hotel and airline program has a dining program. Enroll with the program and register your credit cards. Then, each time you dine at select restaurants, you can earn up to five miles per dollar spent, including tax and tip. You don’t even have to mention it to your server. The miles simply post.

Online shopping. Most airlines—and even credit card reward currencies like Chase’s Ultimate Rewards—have online shopping portals where you can earn miles or points for your regular shopping. Just log in through these portals and then click through to the merchant (Bloomingdale’s, J. Crew, Pottery Barn, Target, and others). If you’re already shopping online, you might as well get some extra points for it. Sites like can help you figure out which portal has the biggest bonus for each store.

Booking hotels. Many of us have to book business travel through our company’s agent or a specific website. But for those of you free to make your own bookings, consider those same shopping portals. You’ll find hotel groups like Marriott, as well as online travel agencies like Travelocity and Expedia. If you book directly on the hotel’s website, you get your points and credit toward elite status (not so with the online travel agencies), as well as extra points for using the shopping portal to get to the hotel’s site.

Keeping miles alive. Those portals are also a great way to keep miles from expiring. Most airlines require some form of account activity once every 18 months. Buy one song at Apple’s iTunes for 99 cents via a portal, and you keep all your miles active for another 18 months. Don’t want to buy anything? Just redeem miles for a magazine and the clock resets.

Distance-based awards. Generally, you need 25,000 miles for a free domestic round-trip coach plane ticket. But there are ways to get some flights much cheaper. British Airways offers distance-based awards, including those on partner American Airlines. Want to fly from New York to Florida? It will cost you only 15,000 British Airways miles—a savings of 10,000 miles. Chicago to Toronto is an even better deal at just 9,000 miles round-trip. Don’t have British Airways miles? You can transfer them from American Express Membership Rewards and Chase Ultimate Rewards.

Longer hotel stays. Bob Behrens, vice president of operations for Marriott Rewards, reminded me that “most hotel programs have a sweet spot for redeeming multiple-night awards.” It’s a great tip. Marriott, Starwood, and Hilton (for elites only) give you the fifth night free when redeeming points. That works out to a 20-percent nightly discount. If you’re not an elite member of Hilton’s HHonors program, sign up for one of its credit cards that gets you entry level.

Hotel rooms and air miles. Starwood and Marriott both offer package redemptions where you can get free hotel nights plus a transfer of airline miles. For instance, Starwood’s “Nights & Flights” option offers five nights at a category 4 hotel and 50,000 airline miles for 70,000 points. Five nights at that category would normally cost 40,000 points. So for an extra 30,000 points, you get 50,000 miles. Additionally, Marriott offers travel packages, including seven nights at a category 6 hotel plus 55,000 airline miles for 230,000 points. Booked separately, the hotel nights would cost 180,000 points and the miles would be another 160,000 points.

Buying elite status. Some airline credit cards will reward big spenders with miles toward elite status. Spend $40,000 a year on the Citi Executive AAdvantage World Elite MasterCard, for example, and get 10,000 elite qualifying miles on American. Spend $30,000 a year on the Delta Reserve American Express and get 15,000 medallion qualifying miles. Spend $60,000, and you get an extra 15,000 medallion qualifying miles. Both cards also come with lounge access (as well as an annual fee of $450).

Hang up, call back.Gary Leff, who runs the blog View from the Wing as well as an award booking service, swears by those four words. When a representative of an airline, hotel, or other travel provider isn’t telling you what you want to hear, hang up and try again. The reality is that some agents know how to find award space when others are, shall we say, geographically challenged. Be polite, but say something like, “I’m sorry, you’re breaking up. Can you repeat that?” Say it again. Then hang up.

Scott Mayerowitz is an airlines reporter for the Associated Press. Read his stories on the AP site and follow him on Twitter @GlobeTrotScott.