Smooth Process of Saving Money and Booking a Flight with Upside + Free Bose Headphones!

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Back in August I wrote about a travel booking site called Upside where they are offering an awesome incentive for first time bookers. At the time if you booked a $400 flight (or travel package), you’d receive a $250 gift card! I immediately took advantage of the offer and booked myself a $433 flight on JetBlue – a flight I had to book anyways. While I paid $433 upfront, I knew that after taking my flight a few months later I’d receive a $250 gift card, which I could redeem at Amazon (amongst many other stores). Instead of thinking of this as a free $250 gift card, I think of it as a $183 roundtrip flight which I am very happy with. I shop at Amazon daily, so I think of Amazon gift cards like getting cash. And a much better deal then using points!

Booking through Upside was extremely easy. The interface is very user friendly and makes the booking process seamless. I was able to include my JetBlue number, my Known Traveler number, and my window seat preference. After I made my reservation I even received a personal email from Upside asking me if I had any additional seat preferences and that they are happy to help me with anything else I may need. I like the personal touch I received and I know there are many business travelers out there that like someone else doing the leg work for them.

This past weekend I completed my flight that I booked with Upside and everything went off without a hitch. My JetBlue number was on the reservation, I received my preferred seat, and had TSA PreCheck stamped onto my boarding ticket. My return flight was on Sunday and when I woke up this morning (about 36 hours later), I had the $25 credit in my account. I immediately redeemed for an Amazon gift card and it was sent to my email within minutes. Again, an extremely easy process and a great way to save money on my flight!

Current Offer – Bose Headset or $100 Gift Card!

While the $250 gift card with a $400 purchase offer is no longer available, there are still a few great promotions going on. You can still take advantage of one of two offers:

  • Bose SoundLink Around-Ear Wireless Headphones II. Use promo code BOSEDEALSWELIKE and this link and book a $600+ flight or travel package. Then 72 hours after your flight you’ll receive a free Bose headset worth around $225. This promotion expires November 30, 2017 (you must book by this date you do not actually need to travel by this date)
  • $100 gift card. Use promo code DEALSWELIKE and this link and book a $600+ flight or travel package. Then 72 hours after your flight you’ll receive $100 in your Upside account which you can then redeem for many merchant gift cards, including: Amazon, Nordstrom, Target, Home Depot, Lowe’s, CVS, Gap, Whole Foods, Staples, etc.

You can learn more about these two offers here. This offer is for new users booking their first business trip, 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 a hotel (or a hotel package), but I found the hotel selections to be limiting and possibly 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. I’ve included my personal referral links above, thank you in advance!

Some Things to Know With Upside

  • 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.
  • You cannot book one way flights.
  • You cannot book two different airlines for your departure and return. If you want to take a JetBlue fight to your destination and a United flight home, for example, that will not work. This is a huge con as many times it is cheaper to book two different airlines depending on how they are pricing out.
  • 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.

For me personally, this was a great way to get a nice deal on the flight I just completed!

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.

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