Upside Adds Domestic Bookings, Offers $200 In Gift Cards

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

In case you’ve missed earlier posts, Upside is a new travel tool that aims to disrupt the business travel market by incentivizing travelers to choose options that save their companies money.

OMAAT readers have had selected access to the various beta versions for a few months now, but Upside officially opened to the public last week, and now includes domestic bookings as well. To celebrate, One Mile at a Time readers can get a guaranteed $200 in gift cards on their upcoming bookings.

What is Upside?

Fundamentally, Upside works by encouraging business travelers to capitalize on their flexibility. The premise is that you might be willing to take a connecting flight, or stay a block away from the conference if there was something in it for you.

Of course, that connecting flight is likely less expensive, and Upside might have been able to negotiate a great rate with that other hotel, so they’re able to offer competitive pricing on their packages, while still rewarding travelers with gift cards. They have a video that sums it up nicely:

I’ve written extensively about Upside previously, so if you have further questions as to how the tool works you’ll want to check those out:

Is Upside a good deal?

Now, as I’ve said from the beginning, Upside isn’t for everyone. The model is geared towards business travelers, but not as much for extreme road-warriors or those with highly-managed travel policies at big companies. Leisure travelers can likely do better elsewhere if they have time to hunt for deals.

For those at smaller companies, however, Upside could be a good fit. For folks who don’t care about hotel elite status, and don’t travel frequently enough to maximize benefits through credit cards, the gift cards could be a nice perk.

Speaking of gift cards, OMAAT readers will get a guaranteed $200 in gift cards on all purchases until February 28th of this year. You don’t have to travel by then, but the 28th will be the last day to book with the $200 guarantee. Just use the promo code “OMAAT” when making your booking.

Given that the packages are competitively priced for what they are (i.e., not something that is maximizing every possible elite or credit card benefit), the $200 in gift cards make this a potentially very nice deal.

Bottom line

I like the concept of Upside, so it’s nice to see the public launch, and the inclusion of domestic travel packages.

They’ve bitten off quite a bit here, so I have some empathy for the slow-roll out. Hopefully the extended trial period has given them a chance to build best practices surrounding things like changes and cancellations.

In general, Upside seems to be delivering both the traveler incentives and the savings that they’ve promised. The packages I’ve priced have all been competitive, and there are definitely people who will value the one-stop-shop approach.

So if you’ve been wondering about Upside, now is a good time to look at some packages. The $200 gift card minimum is certainly a nice incentive!

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

Link: Get $200 in gift cards when booking with Upside

  1. People should be incentivised to be better citizens instead of being punished for being bad ones.

    All criminals should be set free and given $100 for every week they don’t commit a crime.

    The upside model has practical applications in real life.

  2. @ ted — I suppose in theory, but the packages always consist of roundtrip airfare and hotel, so it might be a bit of a stretch.

    Update: “The total amount of promotion gift cards they receive cannot exceed the total cost of the trip”

  3. I was able to find JFK-BOS with a hotel for one night coming out at $202, so would I be able to get the $200 gift card then?

  4. Can you book it for one night then use the 24 hour rule to change your flight to a later date?

    I have a good friend who can put me up at his place meaning I dont need to pay for a hotel. If i book the worst possible hotel, I can save about $150 on airfare if I can change it for free. Does anyone know if that’s possible with upside?

  5. From using the beta site, they appear to have good options for air travel but we found their hotel choices to be rather narrow & not very useful. As an example, they include one Sheraton in a South American capital (so-so rated) but don’t include a much better Sheraton or another Starwood hotel. On domestic front, NYC hotel options don’t appear to be great either.

    Another improvement would be ability to book two tickets & one hotel room. This would get them more of a leisure market.

  6. As I search it’s very rare that I get anything even worth considering. Since I book for work I’ll keep picking up what I want and will avoid Upside…

  7. I noticed some “other” travel blog is able to offer promo codes with $300 gift card, why don’t you do that as well?

  8. @ GringoLoco — Sorry for the delay, Upside says you can use the code as many times as you’d like.

  9. Tip for someone booking a trip from California to Las Vegas. You can book LAX-LAS or SFO-LAS and select Excalibur as your hotel choice. That will run about $200 midweek. Choose the $200 Amazon gift card and throw away the return. Nice deal while it lasts.

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