How This Guy Scored $7 Flights for a Bachelor Party in Vegas, and Other Travel Hacks

April 14, 2014— -- intro: How would you like to take a vacation to Hawaii for just $5? Or how about flying first class to Paris for a romantic weekend for almost nothing?

It may sound too good to be true, but it’s possible if you know how to “travel hack.”

Bryce Conway, a banker from Columbus, Ohio, is a self-proclaimed “travel hacker” and says he hasn’t paid for a flight for himself in three years.

“Travel hacking is a method of earning a lot of frequent flier miles through things like credit card signups and special promotions and using those miles to book really cheap trips,” Conway, 25, said. “It’s just a way to get around a normal system with a shortcut and travel for free.”

Travel hackers like Conway have turned earning frequent flier miles into an art form, and he has quickly learned how to reap the benefits. A newlywed, Conway said he recently flew all seven of his groomsmen to Las Vegas for a bachelor weekend for just $7 per flight, before taxes and fees. And before that, he said he and his new wife flew to Paris for a long weekend for a total of $10, before taxes and fees.

So “Nightline” invited Conway to a travel-hacking challenge: 12 hours to fly himself to a destination of our choosing from New York City, have lunch and get back without spending a dime. Along the way, Conway revealed a few of his secrets to travel hacking. Read some of Conway’s tips below and watch the video above to find out what happens.

quicklist: 1title: Sign Up for Credit Cards With Special Promotions, Perksmedia: 23322716text: Conway has a stack of 23 credit cards, all of which he opened during special promotions that touted free miles, points or flights upon signing up. He uses different cards for specific travel expenses, and a lot of it has to do with good timing.

“You see all these ads for credit cards that say, ‘Get two free flights, get 50,000 points,’” he told ABC's Rebecca Jarvis, pictured here. “I signed up for a travel credit card, got the points and I jumped on the website the day they arrived … we ended up booking a flight to Panama, and then spent the second half of the week in Las Vegas, and then flew home, it was all five bucks.”

These cards not only help customers save money on flights, but also time at the airport. By signing up for the Delta Gold SkyMiles card, Conway gets priority access, which means he can bypass those huge crowds waiting in line, and he gets free checked bags.

But travel experts say perks with these airline-sponsored cards might soon become a thing of the past. Delta, for instance, announced this year that it would be changing its entire program, making it harder for many to earn free flights and upgrades. Instead of earning miles by how far you fly, Delta plans to reward customers based on how much they spend.

quicklist: 2title: But Don’t Overdo It on the Credit Card Sign-upstext: Signing up for multiple credit cards can hurt your credit score if you’re not careful, so Conway cautioned that travel hackers should be strategic and always carefully monitor card balances. Conway said he uses Excel spreadsheets to keep track of all of his credit cards, points, frequent flier numbers and other information.

“I applied for a card, I got a free flight, if you do that a couple of times and you structure that correctly, that’s OK for your credit score,” Conway said. “If you go out tomorrow for 15 credit cards, not so much.”

Financial planners to whom “Nightline” spoke advise people to limit the amount of credit cards they open, and that every case is different.

Personal finance expert and author of “When She Makes More” Farnoosh Torabi cautioned, "certainly, there are people out there trying to gain in the system and certainly, there are benefits to having multiple 'reward' credit cards, and while there are short-term benefits sometimes to opening up all these 'reward' cards, you have to think long-term. Is it smart for me to have all these credit cards at my fingertips? Depending on your personality, depending your tendency, this could be a disaster."

quicklist: 3title: Don’t Be Loyal to One Airline text: “I am completely not loyal to an airline,” Conway said. “I’m loyal to the price or to where ever I can get the points, so I don’t have elite status that a lot of folks will have because they always fly Delta for work. But that’s the trade-off you get for $5, $10 flights.”

For example, Conway said Chase Bank’s reward program allows customers to transfer points to multiple airlines, which can often lead to better deals, rather than being locked into using one particular airline with an individual airline card, like the Delta SkyMiles card.

quicklist: 4title: Look for Special Promotions on Cars, Not Just Flights text: During our “Nightline” interview, Uber, a car service app that lets users request a private driver for hire or rideshare, was having a special where users who referred a friend got a $20 credit to their account.

Conway said he scored a $20 credit on his Uber account every time a friend or family member signed up using his referral code. After five people signed up, Conway told "Nightline" he had enough credit for a free trip in a private car from a New York City hotel in midtown to LaGuardia Airport, a savings of around $70.

Conway also uses autoslash.com for rental cars. It’s a website that tracks rental car price changes and searches for the best coupons and discounts on rentals nationwide.

“When you go to autoslash.com, you just put in your name and confirmation number and they will be constantly searching for a better rate on that exact same car,” he said.

quicklist: 5title: Check to See Whether the Card Includes a Dining Club Membership text: Conway said he is “always thinking about the points” and some credit cards have promotions that include dining clubs, which can earn customers points for dining at certain restaurants.

“First of all, anything with the credit card you’re going to earn points, but then they have dining clubs and [you can] register your card [online] to earn more,” he said.

quicklist: 6title: Always Do Your Research text: Aside from researching promotions that come with signing up for new credit cards, Conway also scours travel hacker blogs and travel websites, such as rewardsnetwork.com, for alerts to specials he can cash in on.

“Last year alone I earned over 1 million frequent flier miles sitting on my couch, just through online credit card signups and promotions,” he said. “Anyone can do this, as long as you have a decent credit score and can manage that and stay on top of it. Anyone can do it.”