Image: Frank Rodriguez Dehydrated and exhausted, I approach the gate agent and ask if she can find me a better seat for the red-eye to Chicago. "Eight flights in one day?" she asks suspiciously when my itinerary appears on her computer screen. "You one of those United Airlines mystery shoppers?"

I assure her I'm not, and wonder if she'll decide that my strange trip warrants a call to the TSA. But a few seconds later she hands me a new boarding pass. "Exit row, window" she says with a wink. "Write nice things about me in your report, Mr. Secret Shopper."

I wasn't a secret shopper, but I was 18 spine-crushing hours into a knight's tour of airport terminals in Chicago, Las Vegas, San Diego and three other cities. Wired News gave me $500 and a mission: Squeeze as many miles as possible out of those five bills, using the tricks and techniques invented by a subculture of airline hackers called "mileage runners" who specialize in accumulating frequent flyer miles at low cost. Now with more than 6,000 miles and 31 hours booked, my only problem was how to spend the other $224.

Mileage runners are the high-tech nomadic wanderers of the air. Predominantly male, generally obsessed with flying and miles, and typically employed in white-collar careers that involve significant business travel, they scour the web for cheap flights, phoning in sick or using vacation days to fly the longest itineraries they can string together.

Five Steps to a Successful Mileage Run

Booking long, inexpensive flights can help you run up the maximum miles. Here's how:

Use the interactive maps at Travelocity or FareCompare to find a cheap round-trip flight from your home city.

2. Locate full fare and routing rules for the flight. Many sites offer only a truncated version, but Priceline lists the complete rules.

3. Study restrictions that apply to the flight you've chosen, paying special attention to the routing rules, which dictate how many connections you can make and in which cities.

4. Use ITA's Trip Planner software to build specific itineraries that meet the fare and routing rules.

5. Once Trip Planner has located a trip that meets your criteria, attempt to book it on the appropriate airline's website, or on Orbitz, which is powered by ITA's software. If this fails, contact the airline by phone to book the itinerary, being sure to give the agent the fare and booking codes provided by ITA.

A mileage runner might extend his New York to Seattle trip by adding a connection in, say, Miami. Or he might spend 16 hours flying to London, grab a pint at Heathrow, and then immediately board a flight back home. If the price is right, she might fly back and forth between two cities four times in a single day.

For mileage runners, getting there isn't half the fun – it's the whole point.

"I personally find airlines and airplanes to be really neat," explains Joshua Solomin, a 28-year-old mileage runner who works as a software manager in San Francisco. Solomin began running in 2006 after a year of business travel vaulted him into the Premier tier of United's Mileage Plus program, giving him his first taste of the first-class upgrades and other coveted perks that come with elite-level frequent flyer membership. "Mileage runs are a way to maintain that status," he says.

Of Solomin's five runs to date, one of the more impressive was a trip from San Francisco to Tampa via Los Angeles, San Diego and Washington, then back with connections in D.C., Seattle and Portland. Thanks to his Premier status, he earned double miles for the trip, more 16,000 of them, for just $232.

On Sunday, he completed his first international run: a $1,450 round trip between San Francisco and Singapore with stops in Los Angeles, Hong Kong and Tokyo. Sure, he had only five hours in the middle of the night to explore Singapore, but with United's July triple mileage bonus he earned a whopping 78,000 miles. And he flew business class the entire way.

Status is important to mileage runners – Solomin refers to himself as a "United 1K" the way I refer to myself as a writer – but there's more to running's appeal than just the airline rewards. "If you like puzzles, it's lots of fun," says Solomin. Assembling a mileage run means deciphering complex fare rules and pulling together information from up to a dozen websites. It's an achievement that tickles the same satisfying problem-solving centers of the brain as a Sudoku puzzle, and always ends in the deep-rooted human thrills of travel and flight.

To get prepared for my own run, I spent weeks lurking on FlyerTalk.com, a message board that serves as a hub for the mileage obsessed. It's the place where runners post their itineraries, search for deals and seek advice from like-minded mileage hounds ("Need help on AA MR from ORD," pleads one post). From there I learn the basics, then start planning a beginner's trip.

Mileage runner Samir Bhatnagar's first trip between Washington D.C. and San Francisco cost $113, and yielded 27,000 miles.

Photo: Samir BhatnagarUsing Travelocity's Dream Maps, I scour for cheap round-trip flights originating from my home base in Boston. Then I carefully parse the applicable rules and restrictions to figure out when I can travel and to map out various routing options (a BOS-SYR-ROC-BUF-PIT-WAS/BWI-RDU routing rule indicates that if the connections exist, I'm allowed stops in Syracuse, Rochester, Buffalo and either Washington D.C. or Baltimore on my way to Raleigh-Durham).

Finally, I plug potential trips into a little-known travel website run by an airline-software firm that excels at complicated route planning, painstakingly stacking multiple connections like Jenga blocks to create the longest itinerary possible without breaking the fare.

It all seems straightforward enough, but each time I attempt to purchase my flights on Orbitz, a mileage runner favorite that can handle complex, multi-segment itineraries, something goes wrong: There are no more seats, or a connection is too close for comfort.

Finally though, I have my trip. I'll leave Boston on a Tuesday at 6 a.m. and arrive in Las Vegas 13 hours later, making stops in Washington D.C., San Diego and San Francisco. After a six-hour layover in the City of Sin, I'll board the midnight red-eye for Chicago, then fly back through Washington D.C. before finally arriving in Boston at 1 p.m. on Wednesday.

I add it all up using a website called Great Circle Mapper: While the nonstop roundtrip comes in at 4,762 miles, my run will yield 6,356. And the whole thing costs just $275.80.

Image: Frank RodriguezMileage runs began in the 1980s, when the financially shaky and now defunct domestic carrier Eastern Airlines launched a triple-mile promotion for all its flights. With $29 Eastern tickets suddenly yielding up to 6,000 miles, travelers found themselves racking up enough points for a trip to Hawaii in just weeks.

Runs became more popular when airlines tacked new, "elite" levels to their frequent-flier programs in the mid-to-late 1980s. Not only did these provide upgrades and other perks, but the new levels offered mileage bonuses, effectively giving dedicated runners mushrooming returns. Then in the 1990s, mileage running took full flight when the web made it possible for runners to hunt for cheap fares without harassing a travel agent and – thanks to sites like FlyerTalk – form communities and easily share information.

Grueling Schedules, Rock-Bottom Fares

The author books two trips in order to test mileage-runner techniques aimed at racking up maximum air miles for the lowest possible price. These trips aren't for the faint of heart, as the itineraries below show. (Note: The actual flights varied slightly from the scheduled purchases due to some early and late arrivals.)

1. Tuesday May 8:

United #201

Depart Boston 6 a.m.

Arrive Washington Dulles 7:41 a.m.

United #229

Depart Washington Dulles 8:15 a.m.

Arrive San Diego 10:34 a.m.

United #900

Depart San Diego 11:16 a.m.

Arrive San Francisco 12:43 p.m.

United #1590

Depart San Francisco 1:14 p.m.

Arrive Las Vegas 2:55 p.m.

United #1498

Depart Las Vegas 11:40 p.m.

Arrive Chicago O'Hare 5:09 a.m. (+1)

Wednesday May 9

United #524

Depart Chicago O'Hare 6:35 a.m.

Arrive Boston 9:30 a.m.

Total cost: $275.80

2. Wednesday, June 6

US Airways #2021

Depart Boston 5:45 a.m.

Arrive Washington Reagan 7:09 a.m.

US Airways #4312

Depart Washington Reagan 9:35 a.m.

Arrive Philadelphia 10:35 a.m.

US Airways #3335

Depart Philadelphia 11:30 a.m.

Arrive Detroit 1:12 p.m.

US Airways #3482

Depart Detroit 1:44 p.m.

Arrive Philadelphia 3:20 p.m.

US Airways #3044

Depart Philadelphia 5:40 p.m.

Arrive New York LaGuardia 6:55 p.m.

US Airways #2142

Depart New York 8:00 p.m.

Arrive Boston 9:05 p.m.

Total price: $196.41

Founded by Randy Petersen, a longtime mileage aficionado who quit his job in 1986 to start a frequent-flyer newsletter, FlyerTalk today boasts over a half million monthly visits, and is part of Frequent Flyer Services, a 12-company multimedia empire that reports on more than 170 travel-loyalty programs. "When I started this business 21 years ago, people used to tell me to get a real job," Petersen tells me when I reach him in Colorado Springs. "Now they're all jealous."

I ask Petersen how the airlines feel about mileage runs and tools like FlyerTalk that make them possible. "Of course they don't like that so many people are engaged in activities that allow them to get these incredibly cheap fares," he says.

But he adds that savvy airlines monitor the FlyerTalk boards to gather information about how their frequent-flyer programs are being perceived. "With FlyerTalk, you really don't need a focus group," Petersen says. "It's all right there."

FlyerTalk bills itself as "the world's largest frequent-flyer community," offering forums on everything from new routes and information on airline-branded credit cards to travel technology and safety. It also addresses truly urgent issues like which United flights still offer full-sized wine glasses in their first-class cabins. FlyerTalk boasts nearly 142,000 members, and the sections dedicated to mileage running contain more than 192,000 posts divided into 16,984 threads.

If FlyerTalk serves as the heart and soul of mileage running, Cambridge-based ITA Software has become its brain. In the travel industry, ITA is known for selling sophisticated route-planning software to the likes of Continental Airlines, Alaska Airlines and Orbitz. But mileage runners know it for an unadvertised web service called Trip Planner that uses the same engine – ITA makes it available free to test new features and fix glitches.

"It turns the world into our QA department," says ITA co-founder and CEO Jeremy Wertheimer, who seems tickled to learn that mileage runners use his site to search for the cheap, multi-segment flights that form the backbone of many mileage runs.

Mileage runners have mastered Trip Planners' special route language, allowing them to generate trips with very specific properties – "BOS:: DL SLC DL" sends the software searching for a two-segment Delta Airlines trip from Boston with a connection in Salt Lake City, for example.

(See "Behind the Fiendish Complexities of Airfare Pricing.")

My first flight departs Logan on time at 6 a.m., and for the next 13 hours I'm in the air or in an airport. The connections are tight and United's coach seats even tighter, but things go smoothly. I eat several $5 United Airlines snack packs and watch Ed Norton die of cholera in The Painted Veil on the long Washington to San Diego leg. I miss a connection at United's big hub in San Francisco, but I'm put on another flight less than an hour later.

I'm exhausted by the time I arrive in Vegas, and when the nice waitress at the Paris casino buffet seats me in the depressing section reserved for people who travel alone, I'm too tired to even care. My spirits are buoyed when I win $100 playing video poker, and the gate agent who thinks I'm a secret shopper gives me a cushy exit-row window seat. But my flights back to Boston are crowded, bumpy and uncomfortable. When I finally arrive home on Wednesday, I swear I'll never fly again.

A week later I'm fully recovered, and eager to share my tale with a real, hard-core mileage runner and bask in the weary glow of my successful run. I reach Samir Bhatnagar, a Northwest Platinum Elite member, as he packs for a 10-day vacation to Romania and Ukraine, a trip he booked after finding what mileage runners refer to as a "fat fingered fare," on FlyerTalk. Fat-fingered fares are mistakes, often incorrectly entered into reservation systems by the airlines – a $179.00 round trip listed for $1.79, for instance. They're usually honored by the airlines, and FlyerTalk members post page after page of them, along with advice on how to book them without tipping off the airline to its error.

I brag to Bhatnagar about my first run: "4.3 cents per mile. Pretty good, right?"

"Um, I think everyone defines 'good' a little bit differently," he says kindly, before explaining that he typically won't do mileage runs that come in at more than 2 cents a mile. Bhatnagar, a 28-year old hospitality-industry employee who lives in the Washington D.C. area, first became interested in mileage running after attending a FlyerTalk function (Mileage runners sometimes arrange their trips so that groups of them can convene on a certain city for cocktails, dinner and discussion).

His first run was a Washington to San Francisco trip that cost $113 and earned him 27,000 miles. "Do that twice and you've got a free ticket," he explains.

I decide that I need professional help if I'm going to achieve a respectable mileage return for Wired News' money. Desperate, I go looking for Viajero Joven, a shadowy figure who lives on the fringes of mileage running.

Joven's website, EliteHelper.com, helps travelers "reach their frequent-flyer goals" by offering $19 to $49 mileage-run consultations. Fearing that the airlines will blacklist him for helping travelers game their frequent-flyer programs, Viajero Joven refuses to reveal his real name – his alias is Spanish for Young Traveler) – and his site provides no contact information, only a PayPal link.

When I finally track him down, he's at an airport on his way to Europe. "London, Paris, Milan, Rome, Madrid and Athens – I'm using miles for the whole thing," he tells me." But I've got some time if you want to talk." He sounds cool and self-assured – like a man who knows what he's talking about.

Joven is clearly underwhelmed with my mileage-running approach, and patiently explains that living in New England, I should be focusing not on miles, but on segments, which are easier to accumulate in the compact Northeast but still count toward elite qualification. He suggests I look at US Airways, and nixes my big idea for a South American mileage trip ("poor return on the dollar," he explains).

Before hanging up, he reminds me that the summer travel season is a tough one for finding good runs, and urges me to keep the faith. "It takes patience," he tells me soothingly. "And don't just jump at the first thing you find. Think carefully about your goals before you book a trip."

I take Viajero Joven's advice and book my second run with an eye on segments: Boston to Washington to Philadelphia to Detroit, an uncomfortably tight 27-minute layover, then back to Philly, and up the coast to New York and finally Boston. Six segments, 17 hours, $196.00.

The trip goes off without a hitch: I make all my connections and I'm home by 9:30 p.m. I earn only 3,000 miles, but I'm six segments closer to silver status on US Airways – the equivalent of another 5,000 miles. My new rate of return is 3.92 cents per earned mile.

I'm getting better. And I still have $27.79 burning a hole in my pocket.

Behind the Fiendish Complexities of Airfare Pricing

Casinos, Malls Won't Fly

The Boarding Pass Brouhaha

Casting Net for Better Airfares