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New site lets you book cheap travel, get free gift cards

Business travelers are always looking for budget-friendly flights and hotels that also provide comfort and convenience. Planning the perfect itinerary can be tough, but one company is promising to make it easier.

Upside is an innovative new travel platform designed to reward business travelers for booking affordable airfare. After entering their departure and arrival information, users are given round-trip flight and hotel options to fit their needs. Then they’re given the option to choose small changes to their itineraries — like connecting through a different city or staying at a hotel a little farther away. These changes push the price of the ticket down and users are rewarded with a $100-$200 gift card for being flexible with their itinerary.

This idea is the brainchild of Jay Walker, Upside’s Chairman and CEO who also founded Priceline (PCLN) in 1998. His experience working in the world of online travel agents helped Upside raise $50 million in funding, and the company has a current valuation of $200 million.

Upside, which launched on Jan. 16, was designed with mid-sized and small businesses in mind — companies that don’t have large travel departments and need help keeping travel expenses in check. If used by employees, Upside predicts it can save small businesses 10%-15% on the lowest published air and hotel prices.

“When it comes to travel, small businesses get no discounts, no tools, no help, no nothing,” Walker told Yahoo Finance. “This is long overdue and the money raised is an indicator of how much it was needed.”

For users, the platform almost seems too good to be true. The free gift cards are to dozens of popular retailers like Amazon (AMZN) and Nike (NKE), and are delivered digitally within 72 hours of a buying a trip. There’s an unlimited 24/7 concierge-level customer service, and travelers also get to keep their frequent-flyer miles and credit card points when they book at their preferred travel providers.

Personal airline and hotel preferences

Being able to earn miles and points is an important feature for Erika Newmyer, a frequent business traveler based in Kearney, Neb. Still, she worries that the platform asks for too much flexibility. “I’ve racked up so many loyalty points with Marriott that I’d like the option to choose a hotel by the brand instead of always choosing the cheapest option.”

To that argument, Walker reminds users that sometimes it pays to play the field.

“A lot people have an airline preference, but for enough savings for your employer or yourself, most people will take another major carrier,” said Walker. “If you end up with a $300 gift card, you might have preferred another airline, but you’re willing to take the perks.”

While it caters specifically to business travelers, Upside can also be used by leisure travelers — but the platform and perks might not live up to their expectations. Business travelers typically choose comfortable airlines and 3-star hotels, so Upside won’t feature flights for low-cost carriers like Spirit Air or hotels like Motel 6. In other words, you could probably find cheaper options if you looked on another online travel agent. In addition, Upside only allows single-person packages, so those wanting to travel with a group will have to call Upside to add others to their itinerary.

For Chicago-based business traveler Michelle Koenig, Upside has a lot of potential, but lacks one booking feature she frequently uses. “Right away I ran into the problem of not being able to book a day trip, which I do a lot,” she told Yahoo Finance.

Booking a same-day return isn’t currently an option because Upside needs to bundle a plane ticket and hotel in order to provide discounts. It’s also how they make money to provide the gift cards. That said, Upside is just a few days old, and Walker predicts there will be more booking options as the company grows.

“You can expect that there will be options for air, hotels, ground, and restaurants going forward. And since you only need to bundle two things at a time to get discounts, it will give travelers more options when booking,” he said.

Upside works with 1,000 hotels and provides service to and from all US commercial airports and more than 60 destinations internationally.

Brittany is a writer at Yahoo Finance.

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