Get Free Bose Headphones When Buying $600+ Air and Hotel

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Free Bose Wireless Headphones With Air/Hotel Purchase

Upside is the new travel booking site from Priceline founder Jay Walker that launched publicly at the beginning of the year. Last summer I interviewed Jay about his history with Priceline and his new business idea.

They reward business travelers for saving their company money. Normally travelers book what’s most convenient within company guidelines because the employer is footing the bill. But connections, or a different hotel could save money. They offer savings to the employer and gift cards to the employee for taking cheaper options they can live with.

  • Maybe you’ll fly in the night before if it saves more than the cost of a hotel night and they’ll give you $100 in your pocket to do it.
  • Maybe you’ll stay at a hotel a mile away from the conference if it’s cheaper and they’ll give you $150 in your pocket to do it.

Upside asks the question, how much is your flexibility worth if there’s ‘upside’ to you? Are you willing to book a less expensive itinerary if you put money in your own pocket to do it?

They sell travel packages of flights and hotels, that way they can discount without running afoul of parity rules.

And usually this really is going to be for reimbursable business travelers, leisure travels should price flights separately, and hotels separately, and see how Upside’s pricing compares. And compare Upside’s packages to travel packages on other sites.

For both business and leisure travelers though they occasionally run compelling first-use bonuses like guaranteed gift card minimums that make booking through them a no-brainer.

Right now there’s a really interesting one: they’ll give first-time customers who purchase a minimum $600 trip by November 30th Bose SoundLink Around-Ear Wireless Headphones II (S230).

Upside tells me that their customer service investment is what’s actually moved the needle the most with independent travelers. If you call expedia you wait on hold interminably for outsourced agents who can’t help you. Upside built theirs around business travelers who expect concierge-level service, and it’s that service that keeps customers coming back rather than the rebates (though those are nice too).

Free Bose Wireless Headphones With Air/Hotel Purchase

About Gary Leff

Gary Leff is one of the foremost experts in the field of miles, points, and frequent business travel - a topic he has covered since 2002. Co-founder of frequent flyer community, emcee of the Freddie Awards, and named one of the "World's Top Travel Experts" by Conde' Nast Traveler (2010-Present) Gary has been a guest on most major news media, profiled in several top print publications, and published broadly on the topic of consumer loyalty. More About Gary »

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  1. I had good success with
    I received my headphones within a week.
    Use code BSHARExs5u3k
    For free Bose wireless headphones with 600$ purchase by 10/31

  2. Putting everything else aside, the biggest snag I see happening is when the business travelers have irrops on a Thursday afternoon, they call in looking for “concierge-level service” and find out all of the flights are sold out and they aren’t getting home until Friday, and they get pissed off and blame Upside (just like they would blame Expedia or the airline now). Whoever fields the call takes the blame.

    Also, I’m genuinely curious how many business travelers get to book their own travel on an airline and hotel website vs. corporate portal. Any company of meaningful size uses a portal as a means of expense control and governance, so how many people and $ are for business travel that is up for grabs?

  3. The use of a referral code — TWICE — without disclosure and without a native link to the promotion is really, really lame.

    And it completely discounts anything written.

    C’mon Gary, you rail against Delta for hiding their award chart and marking hidden changes to award rules.

    Transparency for thee but not for me?

  4. This is all fine and good until I am caught by expense compliance. There is so much that is ethically wrong with using this service.

  5. I’ve used Upside a few times after confirming separately on and that their price was equal too or a few dollars lower. I also had reason to call into their Navigators and found them to be super friendly, and efficient. Spoke to a real person after only a few rings.

    I will say that their inventory of available flights and hotels is limited. As of a few weeks ago, they did not offer any Delta flights. And offered only a subset of the’s flights in a given day.

    The other minor issue for business travelers (which is their target market) is they don’t break out the airfare from the hotel in a receipt. Which makes it hard to submit for expense reports. You really have to capture that info as you are booking, and do the breakout on the exp. report yourself, and hope your employer doesn’t have an issue with that.

  6. Thank you for this post! My partner and I booked our Thanksgiving travel on October 29th and actually received our headphones yesterday. reat to know that I’ll have these with me for our upcoming travel.

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