Booking Transcon Flights and a Hotel for $7 After Rebates Through Upside

Jan 18, 2017

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Update 1/18/17 6:15pm: Upside is offering a guaranteed $200 in gift cards on all purchases through 2/28/17 when you click here and sign up with promo code TPG.

Despite airline seats getting tighter and the fact that onboard service is “not what it used to be,” we seem to be living in a golden age of travel. Not only are airfares the cheapest they’ve been in at least a decade, but there are also plenty of travel tools available to help us find and book them. Now there’s yet another excellent site: Upside.

Created by the founder of Priceline, Upside is a new travel tool that helps you book a flight and hotel package for your next trip. In addition to giving you the standard discounts you’re accustomed to when booking such a package, Upside also offers you gift card rebates just for using the service. While this makes it perfect for business travelers — and others who get their travel costs reimbursed — it’s also great for those who are looking for the lowest net travel cost.

Upside promises a triple win: matching airlines/hotel with extra capacity with travelers who have flexibility, while saving businesses on travel costs. Image courtesy of Upside.

Officially launching this week after a few months in beta testing — although the “Beta” indication remains for now — Upside seems to have worked out the bugs and is ready for the big time. Last week, I tested it out while it was still in beta. Here’s my take.

Eligible Routes

As part of the beta process, Upside was clearly trying to figure out where it fit into the already crowded market. After initially allowing you to fly to any destination from any US city, Upside cut back to just booking departures from a few major US cities to about 30 international destinations. A couple more iterations later, Upside has reversed course. You can now book from almost any US airport to almost any US airport or many international airports.

Booking Process

Start your search on Upside’s homepage. Image courtesy of Upside.

To get started, just head to Upside’s homepage and enter your origin, destination and how nice of a hotel you want (from 2 to 5 stars). As one of the more price-sensitive TPG contributors, I went with a two-star hotel.

On the next page, you start narrowing down the options. First you choose your flight class of service. For domestic routes — even routes with three classes — you only have the choice between economy and first class. For international routes, you choose between economy, premium economy, business and first class. Next, choose the trip purpose (work, leisure or both).

Be careful when choosing dates and times. Image courtesy of Upside.

Where it gets a bit tricky is the next part — especially for international and red-eye flights. Since Upside is focused on business travel, rather than picking which date and time you’ll depart, you pick which date you need to arrive. Need to arrive Monday morning for that 9am meeting? Upside makes it easy. Just note that you need to arrive by 7am on Monday, and Upside will retrieve the flights to get you there in time.

Strategically selecting dates and times is also helpful if you’re trying to get Upside to price a particular flight option that you found on a site like Google Flights. As Upside no longer allows you to select airline alliance preferences (as it did at one point during beta), limiting the search to only times that include your airline’s flight will help trick Upside into giving you the option you want.

You’re probably going to want to choose a different location than is used for the default hotel search. Image courtesy of Upside.

After selecting the flight you want, you’ll then select your hotel. There’s some trickiness to keep in mind here too. Right now, it seems Upside will default to searching a rather narrow geographic downtown area in the city you picked. There might be cheaper hotels matching your hotel star choice outside this area that aren’t displayed.

If you’re hoping to stay near an office (for a business trip) or an airport (for a mileage run) or are just looking for the cheapest accommodation, you’re going to want to change the location it searches — maybe multiple times.

My flight+hotel package ended up costing $307.

The package that I ended up with priced out at $307 after Upside negotiated $40 off of the published airfare and hotel prices. Just over $300 for round-trip transcontinental flights and a hotel near the airport is already a great deal… but there’s more!

I was offered an extra $200 in gift cards for making my first purchase.

This trip offered what seems to be the minimum of $100 in gift cards. But, as a first-time user of Upside, I had been emailed an offer for an extra $200 in gift cards. Yay for me, right? Well, stay tuned — we’re working with Upside to get TPG readers the same deal.

After both the $100 and $200 gift cards were “offset” against my $307 cost, I’m ending up with transcontinental flights and a night at a hotel for just $7. See more about the gift cards below.

When booking a package, it’s always important to make sure there aren’t better deals out there.

While this price sounded great, I wanted to make sure that I was actually getting a good deal. So, before I booked, I made sure to check ITA Matrix to find out the actual cost of these flights, note the American Airlines fare code and check the mileage for elite-qualifying mileage purposes.

Ticketing Process

Within a few minutes of completing the checkout process on Upside’s website, my itinerary appeared as “Ticket Pending” on Within 15 minutes, the ticket was issued with no problem.

Unfortunately, these bookings probably won’t credit using the AA Special Fares chart.

For those looking for ways to book American Airlines Special Fares flights, unfortunately, it doesn’t seem like Upside bookings will credit as Special Fares — despite the AA Special Fares chart being designed for flight+hotel packages just like this. Generally, data points show that if the “Cost Summary” appears on your itinerary, the flights will credit based on revenue rather than mileage. And, the Cost Summary appears on my itinerary booked through Upside.

For those unaware of the difference, these JFK-SFO-JFK flights will likely earn 2,128 award miles ($193.48 fare x 11 miles per dollar for Executive Platinum elites) rather than 5,689 award miles (5,172 flight miles x 50% rate x 220% rate for Executive Platinum elites) if the flights credited using the Special Fares chart.

Update 1/27/17: Bummer! As feared, this booking posted as a standard AA revenue farerather than as a Special Fare

My flights were auto-added to the American Airlines upgrade list.

I was automatically added to the upgrade list at booking as an American Airlines Executive Platinum. If you’re an American Airlines Gold or Platinum and want to upgrade your flights, you’re likely going to need to log in and request an upgrade using 500-mile upgrades.

Redeeming Gift Cards

Redeeming Upside gift card credits was remarkably easy.

So far, the process has been easy, but I was worried that I might run into problems when I tried to “cash out.” Not so. The same day that I booked my package, I received an email from an Upside “Navigator” confirming my flight and noting that gift cards had been added to my account — $100 for the package and $200 for being a first-time customer. Note: In addition to the $300 I received from booking this package, I received an extra $50 for providing earlier feedback in the Beta process.

A couple of days later, I logged in to my account and headed to the Gift Cards section. There I was able to confirm my balance and review my options. While there are dozens of gift card options, Amazon is the most like cash to me — especially as you can use this balance to buy other gift cards later — sometimes even at a discount. So, I redeemed my entire $350 balance for Amazon gift cards. Just minutes later, I received an email from Upside noting that my Amazon gift card was ready. A few clicks later and the balance was successfully applied to my Amazon account.

Bottom Line

In my experience, the whole process with Upside was top-notch. Once I managed to get the system to give me the flights I wanted, I was easily able to book my flight+hotel package, confirm my bookings and cash out my gift cards. Now that Upside has expanded to include domestic flight options, I can’t really think of a reason not to start with Upside for future flight+hotel bookings. Of course, I’ll price-compare flight+hotel packages on other websites to ensure that I’m getting the cheapest price after rebates. But, for now, Upside is going to be my go-to.

We’re going to run some price comparisons between Upside and similar package providers. What’s your current go-to website for booking flight+hotel packages?

Featured image courtesy of Jongcheol Park / EyeEm via Getty Images.

Editorial Disclaimer: Opinions expressed here are the author’s alone, not those of any bank, credit card issuer, airlines or hotel chain, and have not been reviewed, approved or otherwise endorsed by any of these entities.

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