Review – We compare Upside’s package deals for business travelers with other sites

Posted on October 27, 2016 by in Cheap flights, Emirates Reviews & Skywards review

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Tell me about Upside…

Upside is an innovative package deal site for business travelers, created to benefit both your company and yourself. Upside currently operates from airports in New York, Los Angeles, Boston, Chicago and San Francisco to more than 40 global cities, though new departure and destination cities will be added in the future. review

While aiming to save your company around 5 to 15% in reduced travel costs, Upside also lets you, the business traveler, earn free gift cards on the site, with the amount dependent on how flexible you can be with your travel arrangements. In theory, it seems to be a win-win situation, because in addition to the savings and freebies, Upside also does the legwork for you once you’ve given them your travel itinerary. We take a look to see if Upside works in practice by comparing package deals on their site with those on other sites.

How do I use Upside?

The site is super-simple to use and has a good-looking interface. Register for a free BETA account and log in, then choose ‘START A NEW TRIP’ from the homepage and enter your travel requirements. The Upside Flexibility Engine finds custom flight and hotel options for you and the best ones are displayed with gift card values. The highest amount gift cards are for cost-saving travel options that may motivate you to be more flexible.

In this example, if you choose the Piccadilly London West End hotel, you get a $10 gift card, whereas the other options offer you much more – between $324 and $393 in gift cards. review Review – Business class flight travel comparison

It can be a little fiddly to compare Upside with vacation package sites; with the former, you select your flights first and then choose your hotel, but with Orbitz and Expedia, for instance, it’s the other way round, so you may need to play around with dates, flights or hotels a bit.

We checked San Francisco (SFO) to Dubai (DXB) for March 12th to 16th, 2017. With the flight arriving March 13th, that gives us 3 nights in the city. We chose Emirates Business Class flights and the 4* JA Ocean View Hotel, which came up at a grand total of $7,978.23 on Upside, with $300 back in gift cards: review review

On Orbitz, selecting the same business class flights and hotel stay came up at $10,058.79 instead – more than $2,000 than booking on Upside: review

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We also searched for a trip between New York (JFK) and Munich (MUC) from February 16th to 20th, 2016, to compare with Expedia ‘Bundle Deals’. Choosing an overnight flight on Upside gave us a lot more in gift cards – $1,019 – making it a 3-night stay in the city. However, Expedia couldn’t find the same return flights as Upside, so we had to try a different search.

We then tried a search for New York to Munich from March 6th to 9th, 2017. Choosing an overnight outbound again gave us a lot more in gift cards – $1,251 – as well as $101 for selecting the Aloft Munich for the 3 nights. The total price for booking on Upside came out to $4,287.60, including a whopping $1,402 back total in gift cards.

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Booking the same business trip on Expedia came out to $5,341.61 total –  more than $1,000 more expensive than the total on Upside and that’s not even including over $1,400 that you earn in free gift cards! Review – Economy class flight travel comparison

We also checked the cost of an economy flight and 4* hotel package from Los Angeles to London, for a week starting December 14th, 2016, to compare with a DIY trip. With round-trip Virgin Atlantic Economy flights and 7 nights’ stay at the Strand Palace Hotel (a flexible booking which can be cancelled with the hotel the day prior to check-in), the total package price is $1,840.86, though you get $394 back in gift cards: review review

Booking the flight direct with Virgin Atlantic came up at $1,079.06 and booking the same flexible rate direct with the hotel in a Cosy Double came up at $1493.67, totaling $2,572.73 – making it $731.87 cheaper on Upside before you even count the $394 in free gift cards! review review


Upside is a great idea and has a well-designed site that is easy to use, and in all our tests they were clear winners in cheaper business travel packages. However, the site seems to have teething issues, like lacking in consistency and pricing information. There’s no way to save a package search as yet, which is frustrating when you want to save possible bookings to compare elsewhere. When I chose business class flights, it showed me economy, too, which is hard to notice at first and a little annoying; there should be options for business only, economy only or both. Plus it seems like you can only book flights up to mid-March, 2017, right now. A major issue we foresee is that you more than likely won’t earn any stay credits because of booking through a third-party, though you should get your elite benefits. It’s best to weigh up the loss of any stay credits with a potential monetary saving before booking your stay.

While it’s possible that it could benefit your company (and at the same time provide you with free gift cards for not much work), Upside is aimed at rewarding business travelers who can be flexible, with the biggest savings and gift cards going to those who are ultra-flexible. In business, that’s not always possible, but if it sounds like something that you may advantage from, it’s worth signing up for a free account and at least comparing prices before you book your business travel.

Use our link to get an additional $125 off your first booking using

About the author: Torsten is a serial entrepreneur who started almost a dozen ventures on four continents. Torsten's love for travel has brought him to 130+ countries and travel with most of the world's airlines. You can reach Torsten at [email protected]

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