9 Answers To Upside Travel Questions

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

Last week I introduced Upside, a new travel app that aims to disrupt the business travel market by incentivizing travelers to choose options that save their companies money.

As a reminder, One Mile at a Time readers who register this week receive a guaranteed $150 in gift cards on any trips booked in 2016, which is potentially a very good deal!

The app itself is simple, but as with anything new, there have been quite a few questions, so I figured I’d go through some of the most common.

Will I still earn frequent flyer miles with Upside?

Yes! Upside is trading gift cards for flexibility, so while the app might steer you towards a less expensive flight, you won’t be buying a consolidator fare. You can still earn miles on your ticket, just like you normally would.

On top of that, you can still leverage your airline elite status — including potential upgrades.

American-Business-Class-A321 - 30
Upgrades *and* sundaes, even

You can also take advantage of any credit card perks. The Delta SkyMiles® Gold American Express Card and Delta SkyMiles® Gold Business American Express Card, for example, provide baggage discounts and other benefits regardless of which credit card was used to purchase the original ticket. Booking through Upside doesn’t change that.

What about hotel points and elite benefits?

In theory, you won’t receive hotel loyalty program perks from any 3rd-party bookings.

Welcome amenities are an elite benefit, which you’ll forgo when using Upside

In practice, some hotels will honor elite benefits, though you still won’t earn stay credits. Treat this as a surprise if it happens, and don’t plan on earning hotel points when you book through Upside.

I still think Upside will be valuable at chains outside of my usual, or for those that don’t travel quite enough to reach top-tier elite status.

I’ve had bad experiences changing or canceling flights booked through OTAs. How will Upside be different?

We haven’t had a chance to see this in action yet, but one major difference from other online travel agencies will be the service-oriented approach Upside is taking.

The $35 booking fee goes towards staffing a 24/7 customer service line, with agents who will be exclusively dedicated to booking (and rebooking) business travel.

What kind of business travelers is Upside geared towards?

While anyone can use Upside, the focus is on business travelers with “lightly managed” travel policies. Many small-to-medium businesses ask their employees to book the “most reasonable” option versus having strict rules. In many cases these employees even use their personal cards to book travel, and submit for reimbursement later on.

If you’re booking directly, you can make a personal evaluation as to what your flexibility is worth. Upside may offer you $100 to fly into JFK versus LaGuardia, for example, or to stay at a nice hotel a block or two away, and you can decide if that makes sense to you on that particular trip.

Upside will suggest alternate hotels that are equivalent or better than the first pick

How will companies save money if their employees use Upside?

Unless your company is able to negotiate directly with travel providers, most companies will benefit from having fewer restrictions on their travel policies. We see this all the time with the small businesses we work with, where allowing folks to purchase premium cabin fares or leveraging miles ends up being less costly than rules that require economy travel. So liberalizing travel policies can already provide a cost savings.

First class tickets can provide a better value than you might think

To take that a step further, let’s use the earlier example of flying into JFK versus LaGuardia. The flight to JFK might be $200 less than the flight to LGA. You might not have even considered JFK as an option (because let’s face it; it’s less convenient), and you may not be personally invested in helping your employer save $200. But if you get some of that back as a gift card, and your employer realizes a reduced cost as well, everyone wins!

Upside is estimating these tradeoffs and incentives will help employers will save between 5% and 15% on their travel costs.

Wouldn’t it be cheaper just to book everything separately?

Yes and no. Upside will show you the exact flights in your itinerary, so you could always go an book those on your own.

Many of the hotel rates Upside has access to will be the result of negotiated deals. You may not save much (if anything) by trying to book those same hotels.

How is Upside making money?

Fair question, as I know many have been asking how Upside can afford to give gift cards to travelers while still providing a savings to the employer.

Upside will have increased purchasing power, and will be securing exclusive deals with their hotel partners. Bundling the trip gives them a bit of flexibility in the final price they give travelers. There should be enough wiggle room to incentivize travelers, pass a discounted rate to employers, and still turn a profit.

And keep in mind the $35 service fee will cover some of Upside’s expenses as well.

When will the app be available?

Upside will be available as a soft-launch in September, and the general public in late 2016/early 2017.

So why do I have to sign up now?

Obviously you don’t have to do anything. 😉

But only invited users will be able to download the app in September, so you’ll want to be on the invite list. One Mile at a Time readers who register this week are also guaranteed to get $150 in gift cards for every trip they book in 2016, so there’s really no reason to wait.

Bottom line

I think Upside has a cool concept, and if it works it will be brilliant.

If it sounds interesting to you, you might want to check out founder Jay Walker’s interview today on FoxBusiness:

I’m looking forward to using the app when it launches, and hopefully you guys will be able to take advantage of the VIP access as well.

What other questions do you have about Upside?

Regarding Comments: The comments on this page have not been provided, reviewed, approved or otherwise endorsed by any advertiser, and it is not an advertiser's responsibility to ensure posts and/or questions are answered.
  1. In this world of revenue based mileage earning, being pushed to cheaper fare classes does reduce your mileage earning.

  2. Not earning hotel points is a deal breaker. I normally get to earn valuable points that I can use to take my family on vacation. I also get good treatment based on my elite status with the chains. I might be OK earning less points but earning no points or stay credit means I wouldn’t consider using this tool at all, no matter the savings or gift cards.

  3. @ dmodemd — Of course, but it’s not just lower fare classes. Upside may also suggest different connections or carriers (you pre-approve carriers you find acceptable), so there’s quite a bit of potential variation.

  4. @ Nick — Yep, and I mentioned that in my earlier post. I think it depends how much you travel for work. If you have 50+ nights a year and can earn top-tier elite status with a hotel chain, that may be the better option.

    For others, the math may pencil out in favor of getting gift cards for their work trips, and being a free agent on their leisure trips. With as many credit cards as provide mid-tier status (which often means breakfast and a chance at an upgrade), and the various ways to get luxury perks on hotel stays (Virtuoso, Amex FHR, etc.), there are more options than ever for those who travel less frequently.

  5. @ Mike — We don’t accept sponsored posts. We are one of two launch partners for Upside, which basically means readers have access to the VIP rollout and all those perks.

    The only way to join Upside right now is through the referral links on OMAAT or VFTW (which we do get a credit for); we’ve been told that users who sign up for the VIP program will have the option to refer their friends once the program is fully launched.

  6. Mike – in other words…they directly benefit financially from this post.

    Anytime the word “partner” is used it’s a business relationship.

  7. Tiffany! i completed 2 trips with upside.

    Trip 1: i flew Jet Blue and stayed at a chain hotel that i was not a member of

    Jet blue: Reservation honored my Mosiac Status , and on the return portion i had to change my flight to next day, and the change option was easy and done directly on Jetblue website, ( being a mosiac member i don’t have to pay any change fee and moreover i got 100 USD refund because of the fare difference) . but i had to request for miles as they did not post even after a week.

    and for extra day hotel stay tho, that’s out of my pocket at different hotel.

    Trip 2: 2 separate airlines and both honored my status

    and i stayed at big chain hotel of my preference, and upon check-in , i gave my membership number and 2 days after checkout, i saw the points and night credits added to my account. ( i think i got lucky 🙂 )

  8. We just tested JFKMXP Jan 24-29 and Upsite did 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…

  9. 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!



    They “kindly” asked me to book a new one, with higher fare!


  11. Just testing TUL to BDL and the same flights were $67 more, and the hotels were terrible. Anyone who has been to Hartford before knows the hotels are either good or terrible. They wanted to push the flophouses on me while jacking up the price of my usual Marriott to 2X my normal rate all for $15 in gift cards. Not even worth your time to just look.

  12. Amateur Hour. They got a lot of kinks to work out. Failed multiple times to book a simple $1,200 flight. They asked me to call my bank and wait several hours and try again. Not happening. You lost my business. Cool idea with some benefits for booking with them. Poor execution = lost customers.

  13. My experience with Upside has been really solid. I’ve booked a total of five different week-long trips through the site. Initial gift card rewards were more generous, but they’ve upped their game with other perks like a free Starbucks coffee for your trip, surprise seat upgrades, and more. I’m a fan.

    Here’s my referral link for $100 in gift cards on your first trip of $600+: https://upside.com/promocode/?promocode=jjhbln

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