Free Bose Headphones From Booking a Flight Package

Promo code BOSETPG has been extended until 12/30/17. Enter the promo code when booking a flight, hotel, or package through Upside to receive a pair of Bose headphones.

Earlier this year, I booked a transcontinental flight and hotel package for a net of just $7 after getting $300 in gift card rebates through Upside. Sadly, the $300 gift card guarantee that I used back at the end of 2016 is no longer available. The good news is Upside just launched a new promo along with TPG, which allows new users to get a pair of Bose headphones (a $230 value) for booking a flight, hotel or package through Upside.

For those that want to jump straight to booking, here's the link to do so. Enter BOSETPG if the promotion doesn't automatically load for you through that link.

Now, for the details. In order to qualify for the promotion, you must make at least a $600 purchase by November 30. In order to get the headphones, you must "complete your travel," so keep that in mind with how far out you book your trip. And, as mentioned earlier, you must be a "first-time Upside customer."

Since you need to be a new Upside user to get this promotion, I'll explain how Upside works. Created by the founder of Priceline, Upside is a travel search engine for booking flights, hotels and travel packages. In addition to giving you the standard discounts you'd expect from booking 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. While some website artificially inflate prices in order to show a larger package "discount," I've found that flight prices presented by Upside match those found on flight searching tools like Google Flights. So, you're getting a real discount on the travel while also earning gift cards.

Focused on US-based business travelers, Upside limits flight searching to round-trip departures originating in the United States. Trips must be shorter than 28 days long.

Upside originally launched with only flight and hotel packages, but has since expanded to flight plus hotel, rental car or Uber packages. Or, if you just need a flight or hotel, Upside will now sell each one individually. This is great move as it opens up the service to those that need to book a hotel separately (i.e. part of a group booking).

At the very least, you'll need to make a purchase of at least $600 to qualify for the free headphones. However, to score discounts and earn some gift cards, you're going to have to select more than one option to build a custom package. You can pick anywhere between 2-4 of the options.

Another new feature that Upside has added is the "Partial stay at hotel." This is great when you want to add just a night or two - perhaps covering the other nights via hotel points. In my testing, I didn't find any sort of savings or gift card "penalty" for selecting a partial hotel stay. That said, you'll get more savings and more gift cards the more nights that you stay through an Upside purchase (i.e. $30 gift cards for a 3-night stay vs. $70 for a 7-night stay).

Uber Packages

The Uber option is new since I last tried out Upside, so I did some digging into how it works. Turns out there's a lot to keep in mind here. First, this isn't just a straight Uber credit. Instead you're buying a certain number of promo codes good for up to $25 per ride. If your ride is only $10, you don't get to retain the $15 extra. And you can't save the codes for later. The codes are "valid only during your trip."

Plus, adding Uber to your package doesn't really yield you much savings. In testing, I found that the difference between a flight-only booking and a flight+Uber booking adds $5 of gift cards and $10 in savings. I also found no additional savings between flight+hotel vs. flight+hotel+Uber packages.

So, I wouldn't recommend adding an Uber package unless you need to top off a package to get over the $600 minimum purchase for the Bose headphones promotion.

Bottom Line

If you haven't used Upside before, now is a great reason to test it out in order to score a set of Bose headphones. Just make sure to test a few package options and read the fine print to make sure that you meet the terms of the promotion while still getting a good deal.

If you've tried out Upside before, let us know about your experience below.

This article has been updated since publishing to clarify that a package isn't required to qualify for the promotion. You may purchase just a $600+ flight or hotel to qualify.