The New Business Travel Tool Is Here, But Is It Any Good?

Filed Under: Advice, Business Travel
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Update: Get at least $125 in gift cards when booking with Upside & using promo code OMAAT1

Earlier this year I wrote a post about Upside, a new travel app that aims to disrupt the business travel market by incentivizing travelers to choose options that save their companies money.

One Mile at a Time readers become automatic VIPs, get access to the Beta, and a guaranteed $300 in gift cards for every international trip booked in 2016, which can be a potentially very good deal.

The Upside Beta is now available to those who pre-registered over the summer (if you enroll in the VIP program through OMAAT you should receive an email this week with instructions as to how to create your account), so I thought I’d take the program for a spin and see how the technology measures up.

This is a beta, and the tech isn’t perfect

I think this is worth pointing out before we even get into the functionality. Upside is in an advanced-testing phase, so there are still some things that need work.


I’ve noticed some discrepancies in how fields are labeled, for example, and I (sometimes) have to sign in multiple times.

But, the reservations are correct, and the gift cards are real, and they’re working on the other details.

If you notice other glitches as you’re booking a trip, I’d suggest forwarding them to the support team. They’ve been very responsive, and pretty enthusiastic about getting feedback from travelers.

International trips now, domestic later on

Speaking of feedback, one of the things Upside learned from travelers over the summer was that international travel was a priority. So the beta is launching with an international focus, with packages available from five U.S. cities during the testing period.


Additional gateway cities will be added soon, and domestic travel will follow. VIP members receive a minimum of $300 in gift cards on international trips through the end of the year, which can be pretty compelling.

What are the gift cards?

One of the questions I’ve had was about the caliber of the gift cards.

That might sound ridiculous, but my husband and I have both received corporate incentive certificates that were theoretically redeemable for gift cards, only to find that the there weren’t any worthwhile participating retailers.

The options available through Upside are a bit better, by which I mean that Amazon is an option. Amazon gift cards are as good as cash in my home, so that’s an easy choice.

The full list (at the time of this writing) is here:


Your account shows your current gift card balance, along with your history, so it should be easy to keep track of everything.


I’m told that Upside is looking to add more retailers and redemption options over time, but I think this is a good start, and I’d be perfectly happy getting Amazon gift cards.

Does Upside actually save money?

To find out, I tested a series of international trips, and was surprised by the results. I chose international trips to Dubai, Hong Kong, and London, as I’m relatively familiar with routing options and the hotel markets in those cities, so felt I could make a more educated comparison.

Keep in mind Upside is only available for round-trip international itineraries that include a hotel at this point, and because this is a beta there are limited origination cities. But there seems to be a decent selection of flight and hotel inventory.

Trip #1: New York to Dubai

After asking about your city pairs and allowed/preferred class of service, the flexibility engine comes into play. You’ll be asked the latest time you’re willing to arrive in your destination, and the earliest you’re able to depart:

upside-travel-beta-review-036I was then given a list of flight options, and you can immediately see the tradeoffs. A direct business class itinerary doesn’t require much flexibility on your end, so the payout is correspondingly non-existent. If you’re interested in connecting, or downgrading, however, the gift card amounts can be pretty generous.


This is also an example of one of the tech glitches — you’re obviously not flying JetBlue to the Middle East (it’s a codeshare flight with Emirates), nor are you flying United from Zurich to Dubai if you choose that option (it’s a codeshare with Swiss). But the flight numbers are correct, so it seems to mainly be a labeling issue where codeshares are involved. This can of course have implications for mileage earning and upgrade potential, so if you come across something like this I’d recommend calling in (no additional fee for that), and having one of the Upside Navigators double-check the booking codes.

For this trip, I chose the United itinerary, and then asked for hotels near the Dubai World Trade Center:


I was asked what “star level” of property I was allowed to book, and was then given six hotels to choose from. Again, the flexibility comes into play. There’s no additional incentive for booking the Fairmont adjacent to the convention center, but I could book other five star properties in the surrounding area for varying incentives:


The next screen shows the final trip itinerary, including flight numbers, along with the full price of the package:


Since this is a comparison, I priced the same itinerary using Google Flights, which came out to $3,722:


Upside only suggests flexible/refundable hotel rates, so while you could save a bit by choosing an advanced purchase rate, the best comparison is a flexible rate for ~$667 for the stay:



So the price for booking directly with the hotel and airline would be ~$4,389. Compare that to Upside’s price for the same itinerary (not even factoring in the gift cards):


There’s an immediate savings, which was consistent in all the examples I tried. Impressive.

Beyond that, these comparative savings don’t reflect the actual savings compared to what we were ready and willing to pay. If we had booked the nonstop Emirates flights and stayed at the Fairmont, we would have paid ~$8,273. By being a bit flexible, the price can drop dramatically.

That gap is what Upside is hoping to capitalize on, ultimately.

Trip 2: Boston to Hong Kong

Let’s try another, this time from Boston to Hong Kong. Again, the direct flights don’t require much flexibility, and thus don’t earn much in the way of gift cards:


One thing I would like to see here are more options in premium cabins, even with connections. I mentioned this to Upside, and it sounds like their algorithm prioritize schedules (which makes sense for business travel, I suppose), but I was surprised to not see things like economy flights to New York, Toronto, or Chicago that connected with business class flights internationally. I don’t actually think it’s super reasonable to suggest business travelers sacrifice paid business class options for economy seats on a flight to Asia, regardless of the savings or potential incentives, given the corresponding loss of productivity (which the employer was ostensibly planning on when they agreed to allow the purchase of a business class ticket).

So for my purposes, I chose the nonstop Cathay Pacific flights, then asked for hotels near the convention center.


Upside then asks about hotel preferences, and gives some examples:


In this case there is a lot of variation in the amount of gift cards you can potentially earn. If you’re willing to accept a hotel a bit further away (but still 5 Star), you can receive $454 in gift cards.


I chose the Renaissance, as I think I would personally prefer to be closer to the convention center if I were actually attending an event there.

In this case the Renaissance is offering a “Shopping Spree” package at the same price as the pre-paid rate for a Harbor View room, or the regular rate for a Garden View room. I was pleasantly surprised to see Upside chose the package rate (even if the package itself looks a little lame):


If we were booking direct, the rate for the hotel would have been ~$1,128 for a comparable package:


The flights, if purchased directly, would have been ~$7,173, for a combined price of $8,301. Again, Upside’s price is better, even if you don’t factor in the free gift cards.



With this trip, however, we didn’t really choose to have much flexibility. If I search for flights on those same dates I see quite a few alternative options that would be significantly less expensive:



So I’d like to see Upside add more premium cabin alternatives. Some people might not want a second connection, but others might prefer that over a 14-hour flight in economy, and the whole idea of this is that travelers can choose the options that make sense for them.

Trip #3: Los Angeles to London

For the third trip, I tried a trip from LA to London, but in Premium Economy rather than Business.


Again, I was asked to choose my preferred arrival and departure times:


And asked if I had a preference of airline alliance:


In this case I was given options in Virgin Atlantic premium economy, and then economy options as a trade-off.


I’m more okay with seeing economy alternatives to Y+, as there’s a less significant difference than business class. In this case, I chose an economy option on American (which I could theoretically apply my systemwide upgrades to):


I then asked for hotels near the City, as we’re pretending this is a business trip:


Again, you’re asked to choose a hotel category, and there are some examples to guide the decision:


The assortment of chain and non-chain hotels seemed reasonable, but you can always go back and change the target location as well.


I chose the Andaz because I like the location. though I wouldn’t expect to receive elite benefits or credits when booking through Upside.


This is a perfect example of how Upside rewards flexibility, and a glimpse into how they make money. The refundable rate for the hotel would be ~$783 (ouch for Brits on that exchange rate):


But if I price out those same economy flights, they’re only $835, bringing the package price of booking directly to just $1,618.


Why is Upside so much more expensive in this case? Because we didn’t set out to book economy. Upside’s price is competitive with the premium economy option we’d requested, not the economy option we were willing to accept.

So while you’re still saving a bit compared to booking premium economy directly, you’re paying a higher price than you would if you’d been content with economy from the beginning.

There are some interesting opportunities for arbitrage there, and it makes sense for the pricing engine to take advantage of those. But it’s also something to be aware of as you’re plotting your trips.

Will I use Upside?

Honestly, probably not, but that isn’t Upside’s fault.

I’m not their target traveler — at all. I fly too much, spend too many nights in hotels, and am pretty committed to the hamster-wheel of loyalty programs. I also spend hours every day researching flights, hotels, and know the nuances of fare classes and how to save myself during travel disruptions. I don’t need (and likely wouldn’t appreciate) the extra help and services Upside is offering.

But I will recommend Upside to less-frequent business travelers; my husband’s coworkers, my brother-in-law who travels to quarterly medical conferences, and many of the small businesses I work with. I think this is a solid option for those who wouldn’t be traveling enough to earn/enjoy hotel elite status, or who don’t want to pay for an enterprise travel solution for their office, but do want a more streamlined solution.

Leisure travelers (and savvy OMAAT readers) will typically be better served by leveraging points and credit card rewards for most trips, of course, but those options often don’t work for business trips anyway.

Bottom line

Overall, I’m impressed. As I said in June, Upside isn’t for everyone, but I’m excited about the potential here. Most of the travel innovations we’ve seen are focused on the leisure market, so if nothing else hopefully this will inspire more creativity and competition in the business sector.

In the meantime, Upside seems to be doing what they’ve advertised. In every example I tried I was incentivized for being flexible, and the final cost would have been a savings over booking direct. That’s a good value proposition as it is (especially for those that don’t travel enough to care about hotel elite benefits).

The gift cards are gravy.

I’m very interested in hearing about other experiences, so if you end up booking a trip through Upside please share the details!

One Mile at a Time readers become automatic VIPs, get access to the Beta, and a guaranteed $300 in gift cards for every international trip booked in 2016, so you might as well register just in case. I’m told a referral program is in the works, so for those like me who probably won’t use this themselves, but can think of others it would benefit, I’d still recommend signing up so you can invite friends/coworkers later on.

Have you booked a trip through Upside yet? How did it go?

  1. Sorry, but these examples are flawed. Upside is selling a Flight+Hotel package.

    You should really compare against Flight+Hotel packages offered by other TA’s for the same itinerary. These can often be cheaper than buying separately, that is nothing new.

  2. @ Dan — I understand that, and I also priced these out on other OTAs. For the JFK>DXB itinerary, for example, Travelocity’s price was $4,210.49, and Expedia’s $4,309.62.

    The point: Upside is competitive, compared to both OTAs and booking direct, and the interface (and service model) is geared towards business travelers. I think it’s worth trying, if nothing else.

  3. I think you are missing the point of their business model. It is for savvy travelers, who understand the difference in comfort and timing they’ll be “giving up” by using Upside and comparing that to the value they get out of the gift cards. Since the employer is paying, they’re basically trading comfort and speed for cash. Upside is betting individuals will take a 1,000 gift card while saving the company 2,000, as this allows the individual to actually make money on a business trip by sacrificing comfort. This also leaves 1,000 left over for Upside. If you don’t mind the reduced comfort or slower speed, everyone wins.

  4. We’ll see if Upside changes business model midstream. I worked at Worldspan when Orbitz was starting up, started as a marketplace for unsold air seats and has since morphed. Priceline had similar changes. I’d be surprised if Upside didn’t do the same morphing…

  5. @ UCDSoccer — Hah, I understand that exactly, but also understand my value-driven audience here 😉

  6. This whole business model seems to be about charging your employer full price, accepting something less and pocketing the difference in gift vouchers. It all seems very underhanded. If your employer paid for what they thought was J and you arrive exhausted for a meeting because you actually flew Y in order to score gift vouchers, you would be fired.

  7. I have about 20 employees with frequent int’l travel, plus my own. One guy averages about 20k/mo. If i knew a) he was paying less overall and was b) incented to pay less overall vs managing to a budget, I’m a happy manager. The savvy traveler who uses upside would still get most of the points (eg alliance flights)… and would save enough in $ credits to pay for the upgraded room when lack of status became an issue on personal trips.

    I spent 30 min on the phone w/ upside this morning giving feedback. My main ask was to have a report-out that says “this is what was paid vs this is what the flight+hotel on would have cost”.

  8. The website is filled with bugs. I just booked RT SFO-PVG on AC in Y in November for ~$550 with ~$525 gift cards (and hotels so crappy I wouldn’t stay in them). Not holding my breath the reservation will be honored since that seems a little too good to be true.

    Also, I did some messing around with itineraries involving business class. On one itinerary, the price was $1500 with $700 back in GCs if downgrading to Y, however, when I went back and selected the direct flight in C option with no gift cards, the package price changed to $2900, still with no gift cards.

  9. @ Laurel — Those don’t sound like bugs, though if you’re a VIP member you should have been offered $300 in gift cards on the total package at the end — not necessarily on single flights.

  10. No, I was offered $530 in gift cards for an itinerary that costed $550. Do you think they are only paying AC $20 for the flights?

  11. @ Laurel — Nope, I don’t think they’re getting much (if any) discount on the flights themselves. My suspicion is that the savings come on the hotel end, which is where travel agencies have traditionally had more pricing flexibility. I also suspect they aren’t paying face-value for the gift cards (though I have no information on any of these details).

    If you’re a VIP, you’re getting $300 guaranteed, so Upside might not be making much/anything on these first few transactions. Getting $230 in gift cards on an itinerary like this doesn’t seem unreasonable, depending on the hotel agreements.

  12. Upside just changed their pricing overnight without any notice. Prices are 20% higher and gift card rewards are 90% lower now. I guess they finally realized their business model is not sustainable.

  13. We just tested JFK-MXP round-trip Jan 24-29 and Upsite does not give any nonstop options, instead it is giving more expensive 1 stop options with AA/BA. The Emirates flights on A380 (which we always recommend at Flystein) are missing completely as well as Alitalia/Delta.

  14. Absurd, I punched in a travel plan to Hong Kong, just to see what Upside could work out and was quoted just over $4,000 when I can book the entire itinerary, myself, for $1,900. I figured this would not be even close to what a sharp travel shopper can find, without too much energy or effort.

    Buyer beware!


  15. Decided to look at upside and compare prices to a trip I already have booked. Flight from Washington DC to Shanghai and one week’s stay in Marriott Renaissance… Actual economy fare and room was less than $2500… Upside cost for economy fare and room, over $9700.

    Needless to say I won’t be using Upside

  16. I just discovered Upside and wanted to see what others were saying as I thought “this is too good to be true”. Flying from FLL to LAX 3 days from now (read: low availability) and staying 4 nights. Since Delta took away their nonstop for that leg, all the others have skyrocketed and the cheapest I could find online was over $500 one-way. I was going to settle for a connecting one-way on Southwest for ~$250 and stay at the Standard Hollywood where I have a corporate rate which saves me about 30%, my room would have been ~$285/night. So altogether about $1400 not including a return ticket. Comparable round-trip packages I was finding on other third-party sites were over double that price…

    I clicked an ad for Upside and result was a package for round-trip, nonstop air with Virgin airlines at the exact times I wanted +4 nights at Petit Ermitage (which is far nicer and more expensive than the Standard), already for less than the packages I was finding on other sites. Plus $900 in gift cards I could opt to apply to the cost of the trip instead. Bottom line: I got it all for $1100 – almost the same price as just the round-trip nonstop airfare with Virgin.

    Turns out Petit Ermitage was sold out, so after booking I was offered suites (not standard rooms) at Mondrian or the London as alternatives for the same price (all 4-5 stars, all usually far more expensive than what I pay at the Standard). Even if I have to extend my trip, I’d only pay the standard change fee with Virgin ($200), which is still cheaper than any alternative and Upside will negotiate an extended discount with the hotel. A bonus worth mentioning: 24 hour free cancellation on all bookings.

    My only worry – I wonder if this huge savings was because it was my first time booking with them? Or could I find major savings like this again in the future? If so, this is a huge jackpot for me as I’m a small business owner and am doing this same itinerary every few weeks…

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