Do you have the freedom to select your own travel suppliers on business trips – and are you flexible? Would you like like a $200 Amazon, Whole Foods or Home Depot gift card with your next travel booking? If so, you’re the target for for Upside, which officially rolls out this week.

Below, I put it to the test for an upcoming trip to NYC– it found a slightly better deal that I could, and offered me a $200 gift card. Not bad! We also gave Upside a whirl on an Atlanta-Los Angeles trip and it really performed. (See below) Try it to see what it can do for you.

Here’s some background: Upside was put together by a small group of former Priceline executives, including Priceline founder Jay Walker, and has been in beta since last fall. Walker told TravelSkills: “Most business travelers have a valuable, hidden asset that’s worth a small fortune on every trip they take. The asset? Flexibility. Specifically, small amounts of flexibility on the flights and hotels that a business traveler is willing to use on any given trip.” This week the company snagged a cool $50 million investment, and is now valued at about $200 million.

Here’s how it works: Instead of booking your usual first-choice airline, flight time and hotel, you let the Upside website put together an air-hotel package using suppliers that you have pre-approved. Once you decide if the alternatives work, and if the discounts and gift cards offers are enticing enough, you book the trip.

Upside says that you will typically see gift card amounts of $100 to $200, and savings of 5 to 15 percent in travel costs, and enough to make the $35 fee a wash. However, during the current launch period the $35 is waived.

The electronic gift cards are good at 50 major stores or online retailers (such as Amazon or Whole Foods), and they will be delivered to your mobile phone shortly after you buy the trip arrangements. Upside says that those who take just five or six trips a year through Upside can easily rack up $1,000 in gift cards – or more, if they travel internationally in business class. (That will definitely help lower my Whole Foods bill!)

Users will be able to book their arrangements through the Upside app or its website; round-the-clock phone support is also available. There’s no requirement to buy the package Upside suggests, and once you do, it can be cancelled or changed quickly if circumstances warrant.

Upside says that users will earn airline frequent flyer miles for the flights it selects, but they will not earn hotel points. Important: While you will earn airline miles/segments, you will only ear elite qualifying miles/dollars when booking American or Alaska Air with Upside (for now, at least). UPDATE: Currently, Delta is not offered on Upside.

Another important point: Upside purchases code as “travel” so you’ll earn credit card bonuses, such as the 3x points you get for Chase Sapphire Reserve or Barclaycard.

So how will Upside  make money? “We buy travel from suppliers at very advantageous rates– rates so low that we can pass along a substantial discount, take our cut and provide gift cards to travelers,” said a company spokesperson.

Are you willing to give it a try? That’s the question Upside is waiting for you to answer, and they are dangling a nice carrot — a  gift card — in front of travelers to get them to try.

Updates: 1) The Upside app will roll out next month so for now just use the website, which works from smartphones. 2) Currently, Delta and Southwest Airlines do not work with Upside. 3) To change seat assignments, you must visit individual airline site after Upside reservation is completed.

The Test: San Francisco-New York City for two nights

I tested Upside for a business trip I have to New York City in two weeks (Feb 1-3). I want to fly United to get my MileagePlus miles and premier access to economy plus seats, and I prefer to fly into Newark so I can take the train into the city and stay at a hotel near Penn Station.

On the United website, I was able to find flights departing SFO on Wednesday morning and returning Friday evening from Newark. The fare was a great deal– just $237 round trip.

For the hotel, I chose the new(ish) Best Western Premier Herald Square, where I’ve stayed many times before. Rooms are small but clean and quiet, and I love the location near the Empire State Building. Rates on BestWestern.com were equally good at about $100 per night. The total bill for two nights, including room and tax came out to $236.

So I’m looking at a total trip cost of just $473 booking on my own. 

Now let’s take a look at Upside.

I was able to find the exact same United flights and Best Western hotel room. Upside’s price came in at $462.91, about the same as booking it on my own. BUT… I chose a $200 gift card from Whole Foods for booking via Upside. I’ll still earn my United Mileage Plus miles for the flight (but not PQMs). But I won’t get my Best Western Rewards points. Still, that $200 gift card makes booking this trip on Upside definitely worth it!

 

Another test: Atlanta to Los Angeles Feb 14-17 with a 3-night hotel stay in Hollywood.

Booking on Delta.com, we found convenient flights departing ATL in the morning, and returning from LAX in the late afternoon priced about $336 round trip. A room at the W hotel Hollywood booked on its website is $313 per night, and for three nights, to total bill including taxes is $1,120. So a total trip cost of $1,456.

Booking the same trip on Upside resulted in decent savings–plus a nice $222 gift card. However, to get the great deal, I’d have to fly on American (nonstop) and stay at the Hollywood Roosevelt hotel instead of the W hotel for a total cost of $1,254.73- saving about $200. 

Plus, I get a gift card good for $222. Done deal!

Take a spin through Upside and see what it can do for you… and report back your savings here!