I receive compensation for many links on this blog. You don’t have to use these links, but I am grateful to you if you do. American Express, Citibank, Chase, and other banks are advertising partners of this site. Any opinions expressed in this post are my own, and have not been reviewed, approved, or endorsed by my advertising partners. I do not write about all credit cards that are available -- instead focusing on miles, points, and cash back (and currencies that can be converted into the same).
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.