My Experience Booking a Flight with Upside

Last week I wrote about an awesome promotion with the travel booking site Upside travel booking site Upside where you could ultimately pay $150 for a $400 flight! Related post. I had a flight I needed to book from Boston to Chicago and the flight was pricing out at $433 so this was the perfect opportunity to take advantage of the offer. While I paid $433 upfront, after I take my flight in November I will receive a $250 gift card. 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.

Booking through Upside was extremely easy. The interface is very user friendly and makes the booking process seamless. Although, I did find a few issues that might cause this site to not work for you:

• 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.
• 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.

After booking with Upside, I received an email from them letting me know exactly what seat they reserved for me and asking for my Known Traveler Number. I could have entered it during the booking process, but I didn’t have it with me. They told me they’d work on getting me a different seat if I prefer window, aisle, middle, back of the plane, front of the plane, etc. I can also go directly on the JetBlue site and hand select my seat as well, which I will probably do. While I absolutely am able to handle getting all the information into my reservation myself, I do like the personal touch and I know there are many business travelers out there that like someone else doing the leg work for them.

Based on the comments I’ve read and after speaking to Upside directly, the gift card will be deposited into your account within 72 hours of your flight. Some even said that they received the gift card prior to their flight! There is a huge selection of gift cards to pick from, including: Amazon, CVS, Nordstrom, Whole Foods, Target, Uber, Netflix, Staples, Gap, Panera, plus many many more. I’ve been told that is an extremely straight forward process to redeem the gift card, but I do not yet have that personal experience.

Unfortunately the $250 gift card promotion has ended, but there is still a promotion where you’ll receive a $125 gift card if you purchase a $400 or more travel package. With this promotion, you do not need to actually purchase a package, you can purchase just a flight if it happens to be more then $400. Or, you can add on some Uber credits if you are just shy. You can book via this link or enter promo code yfw8f0

For me personally, this was a great way to get a nice deal on an upcoming flight I needed to book. The gift card promos are for first time users, so unfortunately it doesn’t seem like you’ll be able to take advantage of this great deal once. However, without a promotion in hand, I am not quite sure I’d use the site again. There just doesn’t seem to be a benefit to me personally. But I do recommend using it at least once!