It's been a bumpy round trip to the ticker-tape landing strip for Orbitz (NYSE:OWW), but it's back. The online travel portal went public at $15 a share, priced below its original IPO range of between $16 and $18 per share.

I guess you could say investors weren't willing to fly too high to get a piece of the company, which includes the namesake site as well as other popular travel sites like and Europe's

Too many missed connecting flights
Orbitz has been passed around more than a hot potato at a suburban toddler's birthday party. The company went public in 2003, but was acquired by Cendant a year later. Then a private equity consortium led by Blackstone (NYSE:BX) acquired Cendant's Travelport business, including most of the Orbitz pieces going public today.

You don't need the marked-down offering price to scare you away from taking a flyer with the stock. A whiff of the prospectus is enough to make you queasy. While other portals, like Expedia (NASDAQ:EXPE) and Priceline (NASDAQ:PCLN), have been consistently profitable lately, Orbitz has never turned an annual profit.

A jokester would lay the blame at the company's roots -- it was initially bankrolled by a collection of money-losing airlines -- but Orbitz has never been able to find a profitable groove despite its clunky family tree. It has been shuffled around from parent to parent like a baby doll in a Lamaze class, but its income statements have always come out bloodshot on the bottom line.

So why should this time be any different? Sure, the company squeezed out a meager operating profit during the first three months of 2007, but don't expect that to last. Part of the deal involves paying a ton of money to Travelport's partners, who will still control 60% of the company. So even after raising more than $500 million in the IPO, that money will be handed over to Travelport, replaced by $600 million in debt and a lack of voting control.

I'm starting to realize why Orbitz went with its particular ticker symbol, and it has nothing to do with Orbitz World Wide, my friend. Today's investors are also buying into a highly dilutive situation. After the offering, Orbitz will command negative book value to the tune of more than $10 a share.

Companies can certainly operate in a state of negative shareholder equity, but it will become that much harder if Orbitz returns to its profit-sucking ways and finds a lack of willing creditors. Just a guess here, but I wouldn't be surprised if the company's first annual report next year comes with airsickness bags in a pouch in the back.

Arrivals and departures
The travel landscape is changing. Yes, online sites are eating into conventional bookings. Orbitz saw its gross travel bookings soar 38% higher last year. However, too many travel providers are establishing direct relationships with their users.

Just think of Southwest (NYSE:LUV) and its Ding service. Creating a desktop application that serves up custom-tailored, last-minute deals? That could be a killer app, quite literally, if more airlines, hotels, and rental car companies get that creative with their consumer-direct marketing.

And even if one argues that online booking sites are important, it's hard to beat the logic of comparison travel shopping sites like Sidestep and Kayak. Those sites are building better mousetraps that scour several portals for the best deals available.

Travel portals aren't going away. They can still broker deals with high-traffic websites -- like Orbitz has in providing vacation packages through Yahoo! (NASDAQ:YHOO) and Intercontinental Hotel Group (NYSE:IHG) -- but acquiring traffic is going to get a whole lot harder in the future with smarter, stiffer competition. A cash-strapped Orbitz is also going to find it that much harder to ink more deals going forward.

I could be wrong, of course. Orbitz could take off with its latest paint job, emerging as a profitable concern with years of tax-loss carryforwards to keep the good times coming. I wouldn't wait for that to happen, though. Travelport could have waited until the company was consistently profitable to take it public at a higher price.

The operating profit generated during the first quarter isn't enough to drum up optimism here. In fact, that $9 million in operating profit during the first three months of 2007 was obliterated by a $19 million tab in interest payments. In short, the company posted yet another loss in the last quarter before it filed to go public.

You're welcome to the pain if you want it, but just keep the OWW to yourself. and Yahoo! are Motley Fool Stock Advisor recommendations. You can take off with the newsletter for a free 30-day trial subscription trip.

Longtime Fool contributor Rick Munarriz still relies on the portals to get basic travel information, but then he runs off to see if better deals can be had directly with the provider. He does not own shares in any of the companies in this story. He is also part of the Rule Breakers newsletter research team, seeking out tomorrow's ultimate growth stocks a day early. The Fool has a disclosure policy, and it's got a better on-time schedule than your favorite airline.