New Booking Site Rewards Travelers for Their Flexibility

27.07.2023 - 18:40 / smartertravel.com / Tim Winship

Turn your travel flexibility into cash. Well, not cash actually. Gift cards. But still, a reward with some monetary value.

That’s the value proposition of Upside, a new travel site from the founder of Priceline.

The company bundles airline flights and hotel nights into packages that both save money on the purchase price and kick back a rebate in the form of gift cards from national retailers.

In exchange for the savings of 5 to 15 percent, and gift cards that “could easily be worth $50 – $75,” travelers are given options to choose alternative airports, alternative flights, alternative airlines, alternative hotels.

Do you really need to book American’s flight to LAX, and stay at the downtown Hilton? How about a cheaper flight into Burbank, on Southwest, with a stay at the Ramada just south of downtown?

The booking app is interactive, showing users exactly how much can be saved by agreeing to a range of trade-offs. And it’s not opaque, like Priceline. Travelers see which suppliers they are booking, and can predetermine which airlines and hotels they will accept as options. The cost: Users pay $35 for each trip booked through Upside.

Upside will launch in beta in “about 10 weeks.” In the meantime, anyone who signs up as a “pre-launch VIP” is guaranteed a minimum savings of $150 for each trip taken through the end of the year.

Upside brings a new level of automation to a process that many budget-conscious travelers already practice, and throws in some gift cards as a rewards kicker.

The booking app, if it works as advertised, will be a handy tool.

The gift cards, on the other hand, are a marketing misstep. As anyone savvy enough to appreciate Upside’s benefits well knows, gift cards’ value is limited by their single-retailer acceptance, and they are rarely redeemed for their full face value. The gift cards should be replaced with cash, even at lesser amounts, or a choice of cash or gift cards, or a choice of cash, frequent-flyer miles, or gift cards. That would be flexibility.

Reader Reality Check

Might Upside be a useful addition to your travel toolkit?

After 20 years working in the travel industry, and 15 years writing about it, Tim Winship knows a thing or two about travel. Follow him on Twitter @twinship.

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