Posted by William Charles on January 21, 2017
Hotel Booking

Published on January 21st, 2017 | by William Charles


Upside Travel Review – Get Giftcards & Savings

Upside (not to be confused with the gas savings program) is an online travel agency focused on business travelers. The idea is that Upside saves companies money by selling travel packages that combine both hotels & flights. They also offer the person actually travelling gift cards as a reward and will try to lower expenses for companies by enticing travelers to stay at cheaper properties with more gift cards. If that sounds a bit confusing, watch the video below.

Sample Booking

I decided to do a test booking to see how Upside compares to other online travel agencies. I looked at flights between LAX & JFK for January 7th – 11th.

  • Flight prices:
    • Upside: $408
    • Skyscanner: $392
  • Hotel prices:
    • Upside: $774.44
    • $727.39
  • Upside Package Savings: $88
  • Upside giftcard: $100

As you can see the flight is $16 more expensive than using another third party and the hotel is $45 more expensive than using another third party. This is more than offset by the $88 package savings discount and the $100 gift card. That being said, it’s also possible to save money by booking through (e.g using a giftcard you should be able to save 20%+ or you can use their loyalty program and a cash back portal for a savings of 17%+).

If we use that 20% discount on hotels as a baseline that suddenly brings the price down to $581.6. Let’s compare again:

  • Upside: $1,093.76 + $100 gift card ($993.76)
  • Other third parties: $973.6

Our Verdict

I’m actually a bit surprised that Upside is priced so well, it’s still cheaper to book with other third parties (and the above comparison isn’t probably favorable to Upside because I choose everything they listed as the cheapest option) so I can’t see myself ever using the service unless they offer a great promotion.

I found the actual website incredibly clunky to use (e.g it was impossible to do a proper hotel search as I couldn’t easily change where I was looking for hotels or search for specific amenities). I also didn’t see any of the features they advertise, e.g I was never offered additional gift cards for making changes to my reservation (although that might have been because I chose the cheaper options).

Personally I wouldn’t want employees using a site like this, as it gives them an incentive to stay at hotels and take flights that might be less than ideal in exchange for additional gift cards. For example, if they have business downtown but end up staying at a less expensive property further out it might actually end up more expensive for the company due to taxi/uber charges or more dead time in between meetings.

It would also just be cheaper to use other third party sites as indicated above, if we don’t count the $100 gift card (and that goes to the individual rather than the company) then Upside would have been more expensive by $120+. Feel free to share your thoughts in the comments below.

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Their site is terrible. I tried to book something but it errored at checkout saying they couldn’t process my card. It didn’t seem to even submit my card info. It immediately errored out. Contacted their rep via chat and they said it’s a known bug (really, a known bug where people can’t make a purchase on your site?!) and to try again later.

Finally got it to book the next day, but later they emailed me saying the hotel wasn’t available. I tried to contact them via chat to fix it but they it seems they removed the option to chat overnight. Finally picked another hotel but my confirmation email never came. I had to contact them again to send me the confirmation email (which I never got for my original itinerary either).

To top it off, there’s no way I can figure out to see your trips. There’s literally no account management page. You can sign up for an account, but you can’t change email, password, or see your trips. Your info isn’t prefilled when making a booking. Honestly I’m not sure what the point of an account is.


Clicked around a bit more and did find there’s an account page though it’s not intuitive at all. Clicking or hovering on your name on the main page or the search pages doesn’t bring you to your account, instead it just gives you the option to log out.

To see your account info you see to go to the gift cards section then hover over your name. It has a section for trips… yet still doesn’t show my trip. And there’s still no way to change your email or password.


I totally agree with what you said. i had the same problem and then some. This is the most stupidest travel company i had ever booked with. I can not believe Ellen from Kost radio is marketing this company! You cant even use the same credit card to book more than 1 staff! I booked 2 flight packages with different credit cards and 1 got “cancelled” due to “security reasons”. What the hell does that mean?? I called to reactivate my cancelled flight package and both US & Phillipines customer service says its still under “review”. What the hell does that mean?? Im not applying for credit! Im trying to book a damn flight! WORST TRAVEL COMPANY EVER!


This just show how much margin is built into hotel and cruise prices. The real price is about 50% of the first quote.


Dont most larger businesses have preferred providers that offer lower rates on both airfare and lodging? And many large companies have internal travel agents who do all bookings? So who is Upside targeting?

From TJ’s experience, I have a hard time believing Upside will be around much longer. Seems another company with a “great idea” but lousy execution and poor attention to details.


This was a good deal a few days ago. I used to find some trip for $250 and they gives $200 gift card. But at that time their payment system is down. Now they lower the gift card to $75 for any trip I searched. What’s worse is they actually price the cheap flight way above the airline’s publish price. For example, Alaska sales many trip from SJC to SAN for $117. But they show the same exact flight as $195 and only gives $75 gift card. There is no point to buy trip from them. And they seems to gives you some really bad route in large airport to make the ticket more expensive. Keep in mind their gift card does not sent immediately. There is no guarantee they will not just broken before you can cashout your gift card. Overall, it was too good to be true a few days before and now become totally useless.


Zero warning “enhancement” from them the other day.

“We’re always looking for ways to get our customers better prices and more rewards, so we’ve enacted new policy that may affect when you redeem your gift card money.

As of March 2nd, the gift card reward you earn for booking a trip will be added to your Gift Card Hub within 72 hours of completing your trip instead of within 72 hours of purchase.

If you currently have a gift card balance for travel you haven’t yet completed, you’ll now need to wait until 72 hours after returning from your trip to use the funds. Don’t worry, this money is yours and yours alone. We just ask that you wait a bit longer to redeem your Upside.

Why this change? We rely on our customers to complete their travel to provide the maximum savings and rewards.”

The email was sent on 3/3, after the policy was already put in place.

Gino G.
Gino G.

Not good on my first try. I was looking for flights between LAX and Tel Aviv. They gave me one option – Aeroflot. That’s it, even though I know from other sites that multiple airlines fly the route. Aeroflot is sometimes the cheapest, but there are numerous reasons why I might not choose to just take the cheapest flight, such as scheduling, layover, frequent flyer status for example. The Aeroflot flight went through Moscow, really out of the way. Then there was a long layover in Moscow. Just giving me one cheap price doesn’t give me the kinds of choices which are very important to me – and probably to most experienced travelers..


Something is Up with Upside. I tried booking a trip this afternoon and I would be getting ~$600 egift card. After I got home, I tried searching the same exact trip and I would get ~$18 egift card AND very limited hotel choices…. Something is up….


I ran a search for an upcoming trip to Chicago and the price came in about $180 higher than if I booked elsewhere, with $18 in rewards. Generally there is heavy inconsistency on this site, and their search is constantly breaking. Priceline’s founder has a great background in consumer travel but questioning whether he really gets the business travel industry and the willingness of companies to let their employees openly book and get rewarded without transparency. A few other companies are doing a similar thing: TravelBank lets you book through their app and if you choose a flight under the average cost of a flights on that date to earn rewards. Rocketrip does a similar sort of thing but they just offer the budget tool so your company would have to sign up I guess. Upside just hasn’t been consistent enough for me to go back to it.

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