A vacation is often planned around a destination — you've always wanted to see Rome, or your brother is studying in China for the semester and you want to go visit. Other times, a vacation is just an excuse to get out of town — does it really matter where you go?
GetGoing is a discount travel site designed for the latter scenario — but with some constraints. You can search for destinations through lists such as "Beaches and Sun" or "History and Culture." Ultimately, you'll pick two sets of flights to two different destinations (two airports in the same region doesn't count). Interestingly, you aren't told the carrier of the flight (though you do know the takeoff and landing time within a half-hour window).
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Then, GetGoing picks your destination — at random. It's not clear if there's an algorithm behind the process that picks the undersold airfare (so they can obtain better rates on their end), or if it's truly at random. The site explains the discounts as such: "Airlines give bigger discounts to flexible leisure travelers." Either way, it adds a little spontaneity to your planning.
But aside from turning trip planning into a game, does GetGoing really provide better rates on airfare? With a recent trip, I was able to find out firsthand.
My two-week vacation in November was initially planned as a staycation — until the weather started to get chilly. I realized I might be able to pull off a last-minute vacation (to someplace warm, of course), but only if I found a great deal. From Hipmunk's Flight Deals email notifications, I saw that I could get to Miami from New York for under $200. But cheap flights are nothing if lodging isn't cheap as well — so after scouring Airbnb, I moved on to WeHostels and found a few decent-sounding places that were near the ocean and in my budget.
But after browsing GetGoing, I saw that flights to Miami were listed under $200 as well — and Puerto Rico was just a few dollars over $200. I checked around — JetBlue had deals to other islands, but not Puerto Rico, and nothing under $200. Other airlines were at least $269 for Puerto Rico — so if I wanted an island getaway, the only option would be GetGoing.
Before completing the process, I noted the hostel in Miami that I liked, and found a similarly priced hostel in Puerto Rico via hostels.com. Once I was sure a trip to either Miami or Puerto Rico would be within my budget, I entered all my payment information into GetGoing — and then I waited.
GetGoing will automatically book your trip. It takes a few minutes (but feels like hours) for the site to choose one of your trips and book it for you. But when it does, the page refreshes to tell you where you're going and on what airline.
I have to say, I was surprised — pleasantly surprised — to find that I was going to Puerto Rico, and on JetBlue. It is my favorite airline, and I was impressed that GetGoing was truly able to offer significantly discounted airfare that couldn't be found in JetBlue's own flight deals.

Since I have a frequent flyer number for JetBlue, I wondered if I could still get points for these flights — and it turns out that I can. GetGoing has a page in "settings" where you can enter frequent flyer information for just about any airline.
I actually got an additional $25 off this flight — a promotion GetGoing offers because I connected my Facebook account to the site.
Would I have been as satisfied with GetGoing if it had sent me to Miami and not Puerto Rico? I'm not sure — especially since GetGoing's airfare for Miami was matched elsewhere. Ultimately, it was worth the slight risk to perhaps get a discounted trip to Puerto Rico — which I did.
Image: Dani Fankhauser