Upside Travel

I was lucky enough to stumble upon Upside when they launched their beta back in 2016 (I came across it via a sponsored Facebook post, of all things). Co-founded by Jay Walker (Priceline), Scott Case & Jon Ellenthal, Upside’s premise is simple: book business travel packages, and in exchange for being flexible about details like airline/hotel brands, travel times and hotel proximity, your company saves money and Upside also rebates you some of those package savings in the form of gift cards.

I have the responsibility of making my own travel arrangements for work, and in total I’ve used Upside to book airfare & hotel for three different trips (two others were cancelled due to weather). While our company offers some guidelines for pricing, I also feel a responsibility to be a good steward when it comes to keeping costs low. And in comparing package costs vs. booking á la carte, Upside definitely makes sense for me & my company.

While I am partial to Delta for flying and the Hilton family of brands for hotel accommodations, booking travel through Upside has caused me to branch out a bit. I’ve had great experiences flying with United & American, and I’ve stayed at some cool hotels beyond the standard Marriott and Hilton brands (to be fair, Upside offers the most popular hotel brands as well, and some even tack on their loyalty points as well).

While airline options are limited to American & United, Upside offers many, many hotel brands.

In exchange for this flexibility and for booking as a package, I’ve earned a total of $490 in gift cards for these business trips. (To be fair, there were some big gift card bonuses for being a beta customer.) You can redeem your gift cards electronically at brands like Amazon, Target, Panera, Lowe’s, and AMC. Each of my gift card redemptions has worked flawlessly, and fast — it’s really awesome.

On top of the gift cards, Upside is all about providing incredible customer service. Here are a few examples of what I’ve experienced:

  • surprise seat upgrades from economy to economy plus
  • special booking promotions like a $200 Netflix gift card
  • awesome chat & phone support when I had to cancel and rebook a trip due to weather
  • a free $5 Starbucks gift card for you to snag coffee on every trip

All of these features are available on both Upside’s website and their accompanying apps for iOS & Android.

Upside’s iOS app lets you do pretty much anything the website can do, including redeeming rewards and chatting with customer service.

What can I say? I’m an Upside fan. The type of business travel I do varies so widely that I don’t need to book these big packages all the time, but when I do, Upside is the perfect fit. And the company has continued to improve since launch, adding features like rental cars through Hertz, one-way flights, and even loyalty points from certain hotel brands. (One upcoming feature I’m super-excited about is multi-city trips, as it would be great for some business travel I have coming up later this year.)

So that’s my take on Upside Travel. It’s a fun way to earn a little extra when you’re booking business travel, and I’ll definitely continue to use it in the future.

Use this link (affiliate) to earn a minimum of $100 in gift cards on your first trip purchase of $600 or more.

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