LAST CHANCE! Free Bose Headset with a $600 Travel Package from Upside!

The travel booking site Upside is offering an amazing deal that ends on December 31, 2017. If you spend $600 or more on a business trip, you’ll receive a free Bose headset – the Bose SoundLink Around-Ear Wireless Headphones II. Or, if you prefer, you can opt for a $100 gift card for the same purchased travel package. There are no extra fees to booking a flight through Upside and they have awesome customer service. I personally took advantage of this deal a few months ago and had a great experience. I highly recommend booking a flight, hotel, or package through their site to receive the headset or $100 gift card!


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The travel booking site Upside is offering an amazing deal that ends in just a few days on December 31, 2017. If you spend $600 or more on a business trip, you’ll receive a free Bose headset – the Bose SoundLink Around-Ear Wireless Headphones II. The trip can include a flight, hotel, uber, or a combo of all three if you prefer! Back in November I completed my first flight booked through Upside and had an all around excellent experience. You can read more about my experience here.

Upside also recently added two enhancements to their site which might be beneficial for many of you:

  • You now CAN book one-way flights. Although you can only do this on your computer. They are currently working to add this feature to their iOS and Android apps.
  • You now CAN book a roundtrip flight with two different airlines. One airline for your departure and a different airline for your return. This is a huge feature that I am happy to see!

a screenshot of a couponThis is a pretty awesome promotion worth about $199. That is the lowest price I found at a bunch of retailers! And from the reviews, they seem like great headphones (I do not personally have them so cannot speak from personal experience).

a black headphones on a white background

This offer is for first timers, so if you’ve taken advantage of a new member promo with Upside in the past, you unfortunately are not eligible for the offer. Remember though, your flight or travel package must be $600 or more. If the flight you are looking to purchase is slightly LESS then $600, you can purchase a package deal and add on Uber credits to get to the $600 minimum. You can also do hotel (or a hotel package), but I found the hotel selections to be limiting and over priced. The best deal is probably the flight + uber option, or just a flight if it is expensive to begin with. To take advantage of this deal, you MUST sign up for an account at Upside and book through a persons referral link. For the Bose headphones on a $600+ package, you can use this link and code BOSEDEALSWELIKE.

a screenshot of a hotelPrefer a Gift Card Instead?

There is another promotion where if you spend $600+on a flight (or package), you can get a $100 gift card(this is instead of the Bose headset for $600+ purchase). While the Bose headphone is a much higher value, if you have absolutely no use for them and prefer a gift card instead, you can opt for this promotion. While not nearly as good of a deal compared to the offer back in August, it is still a nice savings! You can redeem your git cards for many merchants (i.e., Amazon, Target, Home Depot, Whole Foods, Nordstrom, Gap, etc.) and I consider Amazon gift cards the same as cash since I shop there quite often!  To take advantage of this deal, you MUST sign up for an account at Upside and book through a persons referral link. For the $100 gift card on a $600+ package, you can use this link and code DEALSWELIKE.

Two Different Promotion Links:

  • Bose SoundLink Around-Ear Wireless Headphones II. Use promo code BOSEDEALSWELIKE and this link and book a $600+ flight or travel package.
  • $100 gift card. Use promo code DEALSWELIKE and this link and book a $600+ flight or travel package.

If you’ve used Upside in the past, use promo code UPSIDETHANKSYOU where you can receive a $50 gift card on a $600+ purchase. 

My Experience Booking with Upside

I personally took advantage of a deal back in August. This was for a flight I needed to book from Boston to Chicago for early November and the flight was pricing out at $433 so this was the perfect opportunity to save some money. At the time the offer was a $250 gift card on a $400+ purchase. While I paid $433 upfront, within 36 hours after I completed my flight, my gift card was available to cash out!

Booking through Upside was extremely easy. The interface is very user friendly and makes the booking process seamless. From what I saw, flights are also the exact same price as if you were to book them directly through the airline, so you might as well get a kick back! I did, however, find a few issues that might cause this site to not work for you:

  • Fights are the exact same price as if you were to book them directly through the airline
  • You cannot book a flight on Southwest.
  • For many city pairs, a flight on Delta will not display.
  • Currently, all trips must originate in the United States, including US territories. Upside is working on expanding their service.
  • If you are looking to book a package deal with Uber, you can only purchase the Uber certificates in the following increments: $50, $100, $200, and $300. Not only that, they come in $25 credits so if your Uber only ends up costing $7, for example, it will use the entire credit, you will not receive the difference to use on another ride. If you are traveling to a place that does not have Uber, Upside will credit you the price you paid for those Uber certificates.
  • You will earn all miles with flying your selected airline, this includes redeemable miles and miles towards status. However, as of today, United doesn’t allow qualifying dollars to be earned on tickets purchased through Upside. Upside is trying to work with United on this.
  • You will not receive the airline benefits from using your airline co-branded credit card. So if you get a free checked bag by flying American and using their credit card, you will not receive this benefit by booking through Upside.
  • Upside codes as “Travel†on your credit card statement, so if you use a credit card that gives you bonus points for Travel, you’ll receive those points.

Overall, this is a great opportunity to save some money on a flight you are looking to book!

Disclosure: These are my personal referral links where I will receive a gift card for readers who book a flight or travel package through my link. Thank you in advance!

Editorial Disclosure: Opinions expressed here are author's alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post.

The responses below are not provided or commissioned by the bank advertiser. Responses have not been reviewed, approved or otherwise endorsed by the bank advertiser. It is not the bank advertiser's responsibility to ensure all posts and/or questions are answered.

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