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I travel a lot because I’m a world-famous, globetrotting travel writer (Translation: “I’m on the run from loan sharks and their thumb-breaking debt collectors”).

So I book a ton of flights, using Travelocity and Expedia. But now that I’ve found Hipmunk, I never want to use either one again.

Founded two years ago in San Francisco, Hipmunk is an ingenious travel search site that “aims to take the agony out of travel planning.”

Here’s why Hipmunk is better than Travelocity and Expedia:

Hipmunk visualizes your best flight options on a timeline that looks like a TV Guide. This means you can see your best options spread out on a single page. Yep, it’s so simple, you’ll smack your forehead and wonder why you didn’t think of it first.

The startup’s CEO, Adam Goldstein (age 24) created Hipmunk to help travellers who are frustrated by the pages and pages of irrelevant search results you get on other travel search engines.

Instead, Hipmunk ranks your best trips by finding the lowest overall ‘Agony’ scores. This means a combination of the best ticket price, flight duration, and number of stops you’re willing to endure.

There are dropdown menus for you to select preferred airlines, preferred alliances (e.g. Star Alliance or SkyTeam), or to only find non-stop flights. Plus it also tells you which flights have WiFi!

Below is a screenshot of a sample Hipmunk search. I’m pricing flights to San Francisco because my loan sharks never seem to find me there. I’m aiming to travel there on a weekend in mid-March. This is what Hipmunk found (click on the image to enlarge it on your computer screen):

See how easy it is to pick your favourite flights? It’s colour-coded by airline, and the flight durations span the timeline as if they’re sitcoms and movies in a TV Guide. So simple. Unlike other travel search engines, Hipmunk doesn’t force you to click a dozen buttons or make you fend off annoying pop-up windows.

At a glance, I can decide if I want to punish myself by waking up at 4 am to get the cheapo 8 am United flight for $580 which includes taxes and fees (except for baggage). Or maybe I’ll spend the extra $32 to get WiFi — and frequent flyer points — and take Alaska’s 9 am flight to San Francisco via LAX.

One caveat: Hipmunk doesn’t actually sell you flights or hotel rooms. It simply finds you the best deal, then sends you directly to the airlines, supplier, or Orbitz for booking. They also don’t currently find you car rentals or package deals.

In their hotel section, Hipmunk has a cool feature called Heat Maps. Basically it’s a Google street map that ranks the hottest hotels by how close they are to Vice (casinos, bars, and strip clubs), Nightlife, Shopping, Tourism, and Food.

Interesting. So I used Heat Maps to find a San Francisco hotel and selected the ‘Pricey’ and ‘Vice’ options. This is what it found for me:

Post Hotel San Fran

So apparently the best San Francisco hotel that’s close to bars, casinos, and strip clubs (note the ‘Vice’ button on the upper left) is the Post Hotel. It’s located at 589 Post Street in downtown SF near Union Square.

The menu tells me the basic price for a room at the Post is $216. Aha, but when I click the Post’s dot on the Google map…

Post Hotel best price

… Hipmunk finds me an online sale price of $105 via Agoda.com. Sold!

My prediction:

Hipmunk will be a hit with business travellers (and tax evaders/loan-shark refugees) willing to pay more for a hotel that’s actually interesting, instead of the lame, beige, chain hotels that their assistants normally book for them.

— Ken Hegan

Bing: How to become a startup billionaire

Read all of Ken’s Tripified travel posts here and follow Ken to victory on Twitter

Images courtesy Hipmunk.com

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