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.

Contents
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
- Hotels.com:Â $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 Hotels.com (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.
