ENDING: 2 Weeks Left for Guaranteed $200 Rebate Per Trip

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Upside is the new travel booking site from Priceline founder Jay Walker. It finally launched with full functionality last month. They raised $50 million on a $200 million valuation even before they were fully operational. And with all that marketing money they’re significantly overinvesting in getting you to make a booking now.

I interviewed Jay about the new site and about his Priceline days over the summer.

The idea behind Upside is that if you’re a business traveler, you book what’s most convenient to you within company guidelines because your employer is footing the bill. But with some economic reason that benefits you, you’re willing to make trade-offs.

Maybe you’ll fly in the night before if it saves more than the cost of a hotel night and they’ll give you $100 in your pocket to do it. Maybe you’ll stay at a hotel a mile away from the conference if it’s cheaper and they’ll give you $150 in your pocket to do it. Upside asks the question, how much is your flexibility worth if there’s upside to you? Are you willing to book a less expensive itinerary if you put money in your own pocket to do it?

If you’re a leisure traveler, booking on your own, you’d want to price flights separately, and hotels separately, and see how Upside’s pricing compares — but with a guaranteed minimum $200 rebate per trip, even on cheap short trips, it’s definitely worth trying out.

They gave me a promo code VFTW that guarantees a minimum $200 rebate in gift cards on purchases made by February 28. This is better than their ‘standard’ $150 intro offer. You enter the ‘VFTW’ promo code here. They’re a bit ‘too generous’ with this initial offer so definitely look to see if it makes sense to take advantage.

Here’s a 2 night Vegas air and hotel package departing New York I shared before — you can do a $485 package and get more than $200 back in gift cards. They do coach and business, domestic and international.

About Gary Leff

Gary Leff is one of the foremost experts in the field of miles, points, and frequent business travel - a topic he has covered since 2002. Co-founder of frequent flyer community InsideFlyer.com, emcee of the Freddie Awards, and named one of the "World's Top Travel Experts" by Conde' Nast Traveler (2010-Present) Gary has been a guest on most major news media, profiled in several top print publications, and published broadly on the topic of consumer loyalty. More About Gary »

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  1. It’s actually 6 more weeks. You can use other promo codes “200min” or “today200” before 3/31/2017 and receive at least $200 gift card on upside.

  2. I see no ‘Upside’ here. I couldn’t make it work for my trips, even factoring in the $200. They have an interesting business idea but unless it works no one will use it…

  3. Not seeing the value proposition and they are not ready for prime time a number of key airports I fly from/through/to are not even in their database…

  4. Depending if the GC’s are worth anything, a package to Vegas from SEA is $238, so possibly $38…. plus if I get the miles….

    I may bite just to see how it goes, but not holding out a lot of hope seeing as how amateurish their website is.

  5. The uses for this site are limited. I wanted to book a trip including my wife, and it only allows booking for one. It could just as easily be a traveling companion like a business associate. I chatted with a rep who said that after the fact the can help add a second person. That is just ridiculous.

    Also, clicking through your promo link, the savings that came up was $57, not the minimum $200.

    This sure is a beta product, and is not ready for prime time.

  6. @Steve. Did you add the promo code? I believe you have to join and go all the way through booking to the payment page before you can enter the promo code and see the $200 cards.

    Pretty much a PITA.

  7. I thought this was supposed to expire on the 28th and yet when I try to use the promo code, I get the message, “Promo codes are unavailable – call (855) 252-2151”. What gives?

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