Extreme tips for earning free trips

Howie Rappaport has stayed in six hotels on one business trip to boost his hotel reward stays. He also regularly takes the long way to and from home, complete with connecting flights, to rack up airline points.

Consider a recent trip to London: “I could’ve just flown from Savannah directly to LaGuardia, had a two-hour layover, taken a cab to JFK and flown straight over to London.”

Instead, Rappaport, 32, opted to fly from his home in Savannah, Georgia, through Atlanta to increase qualifying miles for elite frequent flier status.

“I got upgraded to first class, had a cup of coffee, then I flew from Atlanta to LaGuardia, had breakfast, had Wi-Fi, had my coffee, had a big seat, all comfortable, fantastic. Then I had that seven-hour layover where I spent the day with my grandparents” in New York before flying on to London, says Rappaport, a frequent flier who works in software sales and blogs for the Frugal Travel Guy.

Daraius Dubash, who runs the blog Million Mile Secrets, is a credit card man. He has 15 credit cards that earn travel awards, and this year, he has earned 900,000 miles and points in sign-up bonuses alone. Dubash and his fiancée have turned those points into first-class trips for two for a fraction of the regular cost.

Rappaport and Dubash, like many of their fellow road warriors, take flying and staying to a whole new level. CNN asked them to share some of their (sometimes extreme) “travel hacking” strategies, tricks they use to bank enough miles and points to take free vacations and earn elite status.

Make the most of mileage

Adding legs to an already planned trip is the easiest way to boost miles, Rappaport says.

Making “mileage runs,” when you fly for the sole purpose of accumulating miles, can make the difference when you’re a little short on elite qualifying miles. The miles that earn elite status usually have to be flown, not earned through credit card purchases or other promotions.

The first time Rappaport made a mileage run, he was 5,000 miles away from Gold status on Delta Air Lines. He found a $210 ticket flying roundtrip from New York to San Francisco on a Saturday.

“With those flights, I made Gold with Delta, which meant more upgrades, more bonus miles, better award availability. … I even made it home for dinner that night.”

That kind of grueling all-day flying is not exactly relaxing, and you have to keep costs down to make accruing those extra miles worth it. Rappaport tries to keep his costs at under 4 cents per mile.

But the resulting elite status means more than just the coveted upgrades for fliers frequently faced with the mounting hassles of air travel.

“You get priority status if the flight is canceled or delayed, and they really take care of you because you’re one of their premium customers,” says Dubash, 32, a former auditor who works in global marketing.

Expense accounts: Check ‘em twice

Rack up free nights with promotions

On the hotel side, a little inconvenience goes a long way toward earning free nights, Rappaport says. He has stayed more than 120 nights this year in hotels, and he’s always looking for promotions that help him with freebies on leisure trips.

Rappaport says, typically, the number of nights needed to get rewards is two or three times more than the number of stays needed. So he changes hotels on the same trip to add more stays to his tally.

On a trip to Baltimore, Maryland, he stayed at two Westins, three Sheratons and an Aloft hotel. The cost to his company? Less than $100 a night.

His cost? “The only cost was me packing up my suitcase every day, checking out, going to another property, checking in. But in return for that, I’m spending eight nights in Hawaii for free.”

Rappaport says he doesn’t move without a good reason, and he moves between properties that are close to each other.

“Without my job, I wouldn’t be able to travel, so I’ve got to make sure that is always number one. That said, when there is a special promotion that focuses on ‘stays’ versus ‘nights,’ I hop, and I hop every single night,” Rappaport says.

Sign up for reward credit cards

Dubash is a pro when it comes to using credit cards to accumulate miles.

“If your goal is solely to use miles, I think you’re a lot better with credit cards, because you don’t have to stay away from your family. You don’t have to commute to the airport; there’s no opportunity cost of your time,” says Dubash.

Most cards have hefty mileage sign-up bonuses that make racking up enough miles for a free ticket pretty easy. It may seem daunting to open up multiple cards, but Dubash has tricks he uses to make sure he doesn’t damage his credit score.

“I make sure that I don’t apply for a whole lot of cards from a bank that uses a particular credit bureau, because that’s a red flag. … And once you open the credit card, your score may decrease from 2 to 6 points, but then it goes back up, because your overall credit has increased, but the amount of money you’re charging remains the same,” says Dubash.

There are only a few cards worth an annual fee, Dubash says, so he cancels most of his cards before the fee is due if he can’t get it waived. He uses select cards only for purchases to earn more miles and uses online billing to keep track of his statements.

It’s important to pay off balances in full and to pay on time, Dubash warns. Otherwise you could compromise your credit score and your miles, plus interest rates are very high.

Seek out promotions

Dubash not only signs up for credit cards to get point bonuses, he frequently browses airline websites for promotions. You can get points and miles for dining, shopping and even getting your dry cleaning done.

“You just register your credit card, look up a dry cleaner in your area that’s participating in that network, and you get additional points for doing something you’d be doing anyway,” says Dubash.

Simply signing up for a promotion before you board the plane can get you additional miles on a trip you’re taking.

“I just had a flight to London in October, and all I did was sign up for a promotion, and I got an extra 25,000 miles just for doing that. And to put that in perspective, 25,000 miles is about one free domestic ticket,” says Dubash.

Combining promotions with signing up for a new credit card can earn you a flight for much less than the price of a ticket.

“American (Airlines) started a promotion with Japan Airlines where I could use American miles to fly (my brother) from SFO-Japan, nonstop on Japan Airlines, and it would cost only 50,000 miles to do it, round-trip. And I signed up for a Citibank credit card this year that got me 75,000 miles just for signing up and spending $500,” says Rappaport.

Words to the wise

Are you a young business traveler looking to get in the game?

Rappaport stresses that you need to find a program that works for you, when both accumulating and redeeming the miles.

“It’s finding a program that works for you on multiple levels. Does it meet your business requirements? Does it meet your travel requirements? Does the airline fly to places you want to go?” says Rappaport.

You’ll have to look for award seats and do your research, Dubash says. Travelers who just call the airlines looking for free seats usually come up empty.

Travel boards like MilePoint and FlyerTalk can help with specifics, and of course, the most important thing to remember is that you’re still traveling for business.

Rappaport says that making sure his travel plans work for his company is key.

“And if it makes me a happier employee by having the capability to do this, then they don’t care. As long as it doesn’t cost anything extra.”