Great Travel Savings & Bonus Gift Cards With Upside

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

I’ve written previously about Upside, a new travel tool that aims to disrupt the business travel market by incentivizing travelers to choose options that save their companies money.

Now that the public version is live, I figured I’d test a few itineraries and see what kind of deals Upside can offer. My husband has a couple of work trips coming up, and since his trips fit the more “typical” style of business travel than mine, it seemed like a great real-life test.

As a reminder, OMAAT readers will get a guaranteed $200 in gift cards on all purchases until February 28th of this year, which is a pretty fantastic deal. 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.

What is Upside?

To recap, the idea behind Upside is that business travelers might be willing to take a connecting flight, or stay a block away from the conference if there was something in it for them.

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.


Overall, the idea is that businesses will save money because business travelers are incentivized to make more economical choices. You can see our other posts about Upside here, for more details on the concept:

There’s a decent variety of gift cards available, with Amazon being the obvious choice for many of us:


Interestingly, airbnb gift cards are also an option, so while you won’t earn hotel points on Upside bookings (though you do earn airline miles!), you could still leverage your business travel into leisure travel.

With that out of the way, let’s look at some examples!

Trip # 1: Portland, Oregon

The first step is to follow the special link, and enter the OMAAT promo code:


This ensures you’ll get at least $200 in gift cards for your Upside package, so you want to enter the code before you do anything else. There doesn’t seem to be an opportunity to enter it at checkout otherwise.


From there, enter your city pairs, dates, and class of service, just like you would on any OTA:


Upside defaults to giving six options for round-trip flights. A great improvement from the beta testing is that they also show you the airline’s published price for the tickets.


Once you’ve chosen your flights, you can then select your hotel. Upside defaults to showing the “city center” closest to your destination airport, but you can choose a more specific location, and adjust the star level as well.


In this case, my husband is actually going to meetings south of Portland, near Lake Oswego. The conference hotel was even one of the options!


Once you’ve selected your preferred flight and hotel, Upside then presents alternatives based on your flexibility.

In this case, two nearby hotels were cheaper, and offered a few dollars more in gift cards:



Or he could have kept the hotel, but changed from the nonstop Alaska flights to a United option, though the United flights are truly horrible from a schedule perspective.


In this case there’s no real benefit to the more flexible options, but the prices of the packages themselves are competitive with the cost of buying direct, even before you factor in the gift cards:


So that’s a pretty good deal, and as he wouldn’t get any elite perks at a Crowne Plaza anyway, is worth sacrificing the potential points earned.

Trip #2: Las Vegas, NV

For the second trip, I looked at a quick, one-day conference in Las Vegas. It doesn’t matter where he stays for this one, so there should be more flexibility.


In terms of flights, Upside doesn’t work with Southwest (or Southwest doesn’t work with OTAs, more accurately), and they have the bulk of the direct flights. Delta also offers a direct flight, but basic economy fares dominate the route, and the non-BE fares aren’t competitive.

Upside doesn’t show basic economy fares or flights on Spirit/Southwest, so all the flight options offered are connections:


For the hotel, there’s a lot of flexibility. Out of curiosity, I went ahead and chose a Days Inn, given that it was the cheapest default option.


The package shows the the total cost for the flights and hotel of $167, along with $167 in gift cards, because the value of the gift cards can’t exceed the package value:


Given that it’s a Monday night in Vegas, there are obviously better options than a Days Inn though. A variety of mid-range hotels on the Strip were available in map view, but I saw the Aria, which is an all-suite property for ~$200 a night:


With the Upside bundle, the package price would be $315, with $200 back in gift cards:


The flexibility packages were interesting too, offering the Signature at MGM Grand (another all-suite property) at a lower price, but with $10 more in gift cards:


Or if you wanted to pay the same price as the Signature for a standard room at the Trump Hotel, you can do that for a few dollars less in gift cards:


The various resort fees and taxes are already bundled in to Upside’s pricing, making this a pretty compelling option for destinations like Las Vegas.

The downside in this particular case would be the connecting flights — that’s realistically not an option for a short one-day business trip under these circumstances, so he’ll probably end up booking directly with the airline and hotels.

Overall though, I think there’s quite a bit of potential here.

What about when the OMAAT promo code expires?

As a comparison, I also wanted to see what the gift card situation looked like without the guaranteed minimum of $200 from using our link. So I replicated the Portland trip exactly, but without entering the promo code.

I chose the same flights, and the same hotel, which meant the Upside bundle was the same price, but with $75 in gift cards:



The alternative packages offered higher amounts of gift cards, as you’d expect, but the difference between the base offer and the flexible offer was greater without the promo code:


Obviously you want to use the OMAAT promo code to get a guaranteed $200 in gift cards on all purchases until February 28th of this year, but it looks like the value is still going to be quite good after that.

Bottom line

I like the concept of Upside, and 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 with the $200 gift card minimum it’s really a no-brainer as long as the bundles suit your plans otherwise. You can use the OMAAT promo codes as many times as you’d like through the end of February, so it’s definitely worth checking out!

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

Link: Get $200 in gift cards when booking with Upside & using promo code OMAAT

  1. I am residing outside U.S. for the moment. Can AirBnB gift card that I would get from this promo be used for properties outside U.S.?

  2. @ J Long — Yes, ~72 hours after purchasing you’ll have available credit in your Upside account, then can choose your gift cards. The balance accumulates, so you can combine several trips for one big gift card, or choose smaller denominations.

  3. I’ve booked five trips in the last week. Best promotion this year in my opinion. I’m out of pocket between $30 to $50 for each trip.

  4. Is there an option to choose only a one night stay on a 2 week trip – I don’t need the hotel. Can I do that?

  5. Can’t get Delta to show up even on routes when they are the cheapest by a long shot. Are they not able to sell Delta tickets for some reason?

  6. Beware this is definitely a YMMV situation.

    I spent a couple of hours looking at seven scheduled trips in different markets over the next 90 days. NOT ONE TIME did the “airline’s published fare” equal what could be found on an OTA or directly from the airline.


    The overall “package price” wasn’t significantly lower than what I could buy separately — modest savings on the hotel end.

    Pump the price of the “published fare” and rebate via gift card?

    IDK, caveat emptor.

  7. @ GringoLoco — That’s interesting, and when I passed your comment along to Upside they were concerned. Did you happen to take screenshots, by chance, or would you be up for connecting with them to share a bit of what you experienced? Sounds like they’re really trying to do this properly, for whatever that’s worth.

  8. Can you confirm with Upside about the resort fees being included in Vegas. I just booked Bellagio it said $35 service fee waived, yet when I called to confirm my reservation the hotel said that I’d still be responsible for the resort fee.

    Is the $35 a booking fee for Upside that is waived? Any clarity you can provide about resort fees would be appreciated .

  9. @ GringoLoco The times listed on the opening page (“arrive before. . .return after…”) have a significant effect. When I changed the default from 12:00 to something realistic for my needs, I saw a DFW-LAX fare drop by over $170, all the way down to the lowest fare found on ITA.

    Now, I’m not saying Upside will always match the lowest fare found on other sites, but I’m having good success so far.

  10. I’m working all day and need to fly out after 3pm. When I return to work, I need to arrive after 9pm.

    It does not look like upside can give me this itinerary. There is no way to say I want to leave after 3PM, so i can only generate flights that leave in the AM…which is not possible for me.

  11. Also, I’ve been chatting with their rep for the past few minutes and learned that they do NOT display any fares with Delta as they only “include airlines that offer us big discounts”.

    Officially, there is also no way to force the system to pick later departure times, so if you are flying home the same day after work, the system will not pick “after 3pm” flights for you.

  12. Question for Tiffany if she’s still monitoring this thread!

    Do you know which credit card we should use for Could we use a Citi Prestige and get 3x for airfare? I also have a Chase Ink which gets 2x at hotels? Any idea how it codes?

  13. Tiffany,
    No show for the outbound flight and hotel but only use return ticket?
    Would it be possible?

    Thanks in advance.

  14. @Tiffany one of those rare times I wish had a Citi Premier instead of a Citi Prestige, a CSR/CSP instead of a Chase Ink…

  15. This is an interesting assessment. Thanks for sharing. I’d looked into it when traveling to Asia on business a few weeks ago and it looked like, for international paid business travel, it was not worth it. The prices for business class travel were not competitive and, while the gift cards were >$1,000, it still didn’t compensate for the inflated prices. However, it looks like it might be beneficial for U.S. travel. I’d written them off, so this was a helpful post.

  16. Is this deal dead?

    I’m only being offered $75 in gift cards. Tried different browsers, cookies/cache, with/without logging in, etc.

  17. @ LRD — Are you following the link in the post and entering the promo code “OMAAT”? You have to go through the link to get the $200 (or the amount of your trip, if less than $200).

  18. Tiffany — I would recommend looking at international fares in coach and business and providing another assessment to your readers. Admittedly, I’ve only looked at NYC-HKG, but that’s an important market. The business fares are nowhere near competitive with online travel agencies or the websites of airlines themselves. I think it’s important to be transparent about that. This may be a benefit in some cases, but there are some clear cut cases where it is very disadvantageous.

  19. I reported yesterday that the promo code was (apparently) not working, offering me only $75 cashback. But, everything is working fine today. Go figure!

  20. I booked a trip on AS and I’m AS MVP Gold.

    The ticket comes up as bulk (fare not available) as per so I can’t even take advantage of the free MVP Gold change or AS’ low fare guarantee.

    My gift card credit shows up as pending. I’ll wait three days to redeem it and see. I may want to book another trip or two. 🙂

  21. You mentioned resort fees are included, however that is just not correct. I’ve stayed at 2 hotels in Vegas so far and have been charged a resort fee. The site is very deceptive as it didn’t say that when I booked and even in your post you mention that they are included.

  22. @ Mark — I agree that’s deceptive, as it clearly says all fees other than airline baggage fees are included. Let me follow up. You may want to contact Customer Care as well.

  23. From a tweet: We have suspended some promo codes as we are experiencing technical issues. We apologize for any inconvenience.”

  24. @ Carl — They have, and we’re seeing what we can do. Apparently some enterprising group of people were making hundreds of attempts to use our code with known stolen credit cards or something.

  25. While OMAAT (and codes from most of the other travel sites) may be gone, using a common three-character abbreviation for America will still get you $200 rebated (in gift cards) AND it doesn’t expire until 31 March!

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