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General Questions

What is Upside?

Upside™ is the innovative, new travel company that makes it easy for business travelers like you to find great deals on flights and hotels – and rewards you for saving your company money with a gift card every time you make a purchase.

By bundling our flights + hotel into a single-package cost, Upside gets access to unadvertised savings that range from 5-10% off regular published online rates. Plus, each time you book a trip, you’ll receive a gift card to your favorite retailer, typically worth $100-$200 on a domestic trip and much more on international trips.

Another Upside is that you keep all the hard-earned frequent flyer miles and credit card points you’re entitled to with every trip. And don’t worry if there’s a change to your travel plans. Even after purchasing an Upside Package, flights and rooms can be modified or cancelled just as if they had been purchased separately. (Airline and hotel rules apply.

Is Upside only for business travelers?

While leisure travelers can certainly enjoy our great savings, Upside was designed to address the unique needs of business travelers.

Because companies foot the bill for business travel, they require their employees to stay within specific budgets for flights and hotels. Often this comes at the expense of the business traveler, who must sacrifice comfort, convenience, or a little of both. Upside recognizes what you sacrifice to save your company money – and we think you deserve something extra to make up for what you give up. So we provide you with multiple travel options that fit within your criteria and save your company money, then we reward you with a gift card each time you book a trip. The more flexible you are with your plans, the more you save and the bigger the gift card.

To ensure your professional needs are met, Upside sells only business-quality flights and rooms at savings your company will love. Questions or issues? Our Upside Navigators are standing by 24/7 to provide top-quality customer service via phone, email, chat, or social.

What type of travel can I purchase from Upside?

"Upside currently sells fully customized, round-trip flight + hotel packages to all major U.S. and international business destinations. Later in 2017, you can expect us to add additional trip types, including multi-city, one-way, and flight itineraries requiring 2 stops in any direction. At this time, all trips must originate in the U.S.

Why does Upside sell only flights + hotel packages?

Simply put, because it saves your company a lot of money and gives you a bigger gift card in the process.

Because of our package pricing, airlines and hotels give us special, unadvertised deals for business travelers. In return, we never reveal our below-retail costs for individual flights and rooms. Plus, you get a gift card for yourself with every purchase. Depending on the package you choose, this gift card could be worth $100, $200, even $300.

Want more Upside? Your package price includes 24/7 access to our team of Upside Navigators, who provide top-quality customer service via phone, email, chat, or social.

How does Upside save my company money?

Upside stands out from the other travel sites by saving you money in three unique ways that appeal to business

  1. Flights + Hotel Packages
    By bundling round-trip flights and rooms into one low price, Upside can negotiate special deals from airlines and hotels that aren’t available to the general public. We agree to keep the deals private by not revealing individual flight and room prices, only the combined price of your Upside Package.
  2. Money-Saving Choices
    Once you enter a few simple details about your trip, our advanced search engine goes to work – seeking out the industry’s 6 best flights and 6 best hotels that match your criteria and provide the most savings.
  3. Flexible Options
    Once you’ve selected the flights and hotel you like best from the Top 6 results (or the additional results you request), we combine them into your Upside Package. In addition, we’ll give you alternative options that have been carefully curated with slight variations (like leaving an hour earlier or staying at a different hotel) that give you bigger savings and an even bigger gift card. You can either choose to stay with your original package or choose one of the alternative options. The choice is always 100% yours.
How can Upside afford to give such low prices and a $100-$300+ gift card, too?

It’s easy. We put you in control of your Upside.

Once you enter your basic travel criteria, our proprietary software analyzes and evaluates every possible itinerary that fits your trip – which can mean 10,000+ combinations on any given trip. We then present you with 6 flights and 6 hotels that best match your requirements (plus a drop-down menu of additional choices). You select 1 option for each, and we combine them into your Upside Package. By bundling your flights + hotel into a single package like this, we’re able to secure special unadvertised savings that we pass on to you – along with a gift card reward each time you make a purchase.

But here’s where it gets even better. With every Upside Package we show you, we also present alternative options: packages that incorporate slight variations in your criteria to provide even bigger savings and bigger gift card rewards. These variations might include a slightly different flight time or a hotel that’s a few blocks away. By choosing to take one of these options, you can substantially increase your travel savings and gift card amount. In essence, you get to choose your Upside. Finally, business travel is on your terms.

How is Upside able to find such fantastic deals?

Our Upside engineers are the best in the business, and they’ve created revolutionary new software that analyzes your search criteria against comprehensive airline and hotel databases — including every flight, hotel, and price — to discover the best travel options that work for you, based on the specific needs of your trip. We look at every option so you don’t have to.

The best options are then presented to you, and you get to choose the one that provides you with the best savings, the most gift card amount, or a variation in between. The Upside is completely up to you!

What type of traveler uses Upside?

While leisure travelers can certainly use Upside, we are geared toward businesspeople who don’t have access to big Fortune 500 discounts or internal travel departments. We provide these professionals with business-quality flights + hotel packages at special unadvertised prices, plus a gift card reward for making travel choices that save their company money.

Why doesn't Upside show me a specific airline or hotel that I want?

While nearly all airlines and hotels are represented, our goal is to provide you with the best prices possible. This means our packages include only airlines and hotels that agree to give us special, unadvertised rates to ensure your company gets great cost savings – and you get a lot of value in your gift card.

Will I receive a receipt for my purchase?

Of course. After you purchase an Upside Package, we will email you a receipt that lists your itinerary, total package cost, plus taxes and service fees. You can see a sample of a receipt here.

Does Upside have a mobile app?

Yes! Our iOS mobile app is available on the App Store. We will be launching our Android app later in 2017.

Gift Cards

How much is each gift card worth?

How much your gift card is worth depends on the specific trip you’re taking, as well as the Upside Package you select. We expect most of our customers will earn a gift card worth $100 to $200 on every domestic trip – and it could be twice that on international trips. The gift card is your reward for making travel choices that save your company money. The more you save, the bigger the gift card.

For some trips abroad, it’s even possible to rack up gift cards worth $500-$1,000 just by swapping out a business class flight with economy. The Upside is up to you!

When will I receive my gift card?

Your gift card funds will be credited to your account within 72 hours of completing your trip. At that time, go your Gift Card Hub to see the amount. You can save the money here for later use, or redeem it immediately for a retailer gift card.

What gift card brands can I choose from?

You can put your gift card money toward any of 50+ national retailer and restaurant brands available, including Amazon.com, The Home Depot®, Nordstrom, Target, and eBay®. You can even choose to split your gift card balance among different brands. 

How do I choose the gift card I want?

It’s easy. Just log into your account and go to yourGift Card Hub. There you can convert any amount of your gift card balance into a retailer gift card. Choose from among 50+ national brands available. Once you make a selection, your gift card will be emailed to you as an egift card, which is easy to use and hard to lose.

Why gift cards? Isn't saving money on travel enough of a reward?

Saving on business travel is certainly a top priority – especially when you who have to stay within company budgets while still trying to find flights and hotels that work with your schedule. Often, you have to sacrifice something – price, comfort, convenience. We think you deserve a little something for going the extra mile, don’t you?

By giving you a gift card with each purchase, we’re saying: hey, your patience and flexibility are worth it. And since you usually save between 5-10% every time you book a trip, your company will love it, too. They’ll want you to return to Upside again and again.

Are there tax implications tied to receiving gift cards?

We’ve been advised that the gift cards earned through Upside are similar to other promotional travel benefits, like hotel points and frequent flyer miles. However, we’re certainly not tax experts, so please reach out to your tax advisor with questions or concerns regarding this issue.

Will my gift cards expire?

The gift card amount credited to your Upside account never expires. However, when you convert any of your balance into gift cards, it is subject to the terms and conditions of the applicable brand(s).

Do I have to use my entire gift card balance at the same time?

Not at all. You can divide up your balance among as many gift card brands as you want, at any time, in any whole-dollar amount.

Package Details

Will I see the details of my package before I purchase it?

Of course. Not only will you see your specific flights + hotel before you purchase, you’ll always be the one to select and confirm them.

What airline and hotel brands are available through Upside?

We include nearly all the same business-quality airline and hotel brands you’re used to, plus top-quality, independent hotels we think you’d like. You will always get to review the flights + hotel you select before finalizing your purchase

Will I still get my airline miles, segments, and dollars when purchasing a trip?

When you book your business trip through Upside, you will always get the qualifying miles and segments you would normally receive for your flights. However, for applicable airlines, you may not receive – or only partially receive – the qualifying dollars. To find out how many miles and segments you will earn, please consult each specific airline’s website.

Do Upside customers still get credit card points and special bonuses?

When you book your business trip through Upside, you will always get the points you would normally receive if you had purchased your travel any other way. However, you may not receive special bonus points that are awarded directly by the airlines or hotels for use of their affinity credit card.

Do Upside customers still get hotel points?

It depends on the hotel. Upside does not apply your hotel points, so you will need to call the hotel or ask at check-in to see if they will apply your points. Many hotels will not give you points if you do not purchase directly from the hotel website, but if you ask nicely at the front desk, many hotels will make an exception.

Referral Program

What is the Upside Referral Program?

The Upside Referral Program is a way for valued customers to share the benefit of Upside with friends and colleagues – and get rewarded for their efforts, too.

How does the Referral Program work?

Once you sign up for an Upside account, you will automatically receive a unique referral code that you can email or post to all your friends and colleagues. When they enter your referral code in the promo code box at checkout, they will get $100 off their 1st Upside package (minimum total package price of $600). In return for spreading the love, you’ll get a $25 gift card once they complete their trip.

Where can I find my referral code?

Simply log into your account, then go to the Gift Card Hub. You will find your personal referral code on the left-hand side, along with some easy links for sharing it.

Can multiple friends use my referral code?

Absolutely. We want to spread the word about Upside, so share your code with colleagues, family, all your Facebook friends and Twitter followers – the more business travelers, the better! And it’s better for you, too. For every person who books a trip using your unique code, you will receive a $25 gift card – so the money can really add up!

When will I receive my $25 gift card for referring a friend?

As soon as each colleague returns from their trip, you will be notified that $25 has been added to the balance in your Gift Card Hub. You can save it there for later, or redeem it immediately at your choice of 50+ retailers, including Amazon.com, Nordstrom, and Target.  The Upside Referral Program is subject to our terms and conditions.

Future Features

Does Upside allow for corporate discounts?

Currently, Upside does not offer corporate discounts since all accounts are created and controlled by the individual business traveler. If your company has an existing corporate discount with a certain airline or hotel, Upside can’t incorporate that discount into our system at this time – but you might find our special rates + gift cards add up to even better savings.

When will Upside add more international destinations?

We have nearly 100 international destinations – and the list is growing regularly. If there is an international destination you don’t see, contact the Upside Navigators at navigators@upside.com and let us know. Currently, all international travel must originate in the U.S., but we are working to change that in 2017.

When will Upside offer international travel that originates abroad?

It’s in the works. In 2017, we plan to add travel to the U.S. that originates from non-U.S. starting points. Please check back with us.

When will Upside sell multi-city and multi-hotel packages?

We’re working around-the-clock to bring you multi-city and multi-hotel package options during the first half of 2017. Please check back with us.

Customer Service

How do I contact Upside customer service?

Our Upside Navigators are available 24/7 to answer any questions you have or help with any issue regarding your trip. Please email us at navigators@upside.com, call us at (855) 252-2151, or reach out on Facebook or Twitter via @UpsideTravel.

To see all the ways you can contact the Upside Navigators, click here.

Is it possible to modify or cancel an Upside Package after purchase?

Of course. We understand that business travel plans change all the time, so we make every effort to accommodate you. That means changes and/or cancellations are no problem, within the rules of the airline and hotel selected in your Upside Package. Our Upside Navigators are standing by 24/7 to assist you. You can easily reach our Navigators here. Email: navigators@upside.com Phone: (855) 252-2151 Facebook & Twitter: @UpsideTravelp>

Where are the Upside Navigators located?

In order to provide you with 24/7 service, we have teams of Upside Navigators located in both the U.S. and the Philippines.

Is there a fee associated with the Upside Navigators?

Because our Navigators are trained travel experts who provide around-the-clock service, it is necessary for us to charge a $35 fee for their use, which we roll into the package cost. This small fee gives you 24/7 access to the Navigators – so contact them as often as you like, for any travel issue you have.

Company Details

Who started Upside?

Upside was started in 2015 by Jay Walker, the founder of Priceline and inventor on more than 600 U.S. patents. Mr. Walker saw the opportunity to serve business travelers by providing flights + hotel packages that save your company money and give you an added gift card benefit for making cost-saving choices. By employing just small bits of flexibility in your schedule, you can really enjoy the Upside.

How many employees work for Upside?

At last count, Upside had more than 50 employees – but we are actively hiring and growing every day! See Upside career opportunities here.

Where is Upside located?

The Upside Travel Company, LLC, is headquartered in Washington D.C., with an additional office in Stamford, CT.