Win Free First Class Domestic Upgrades for 20 Years Through Upside

Mar 14, 2018

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Don’t Miss Out! Enter to win The Business Traveler Dream Sweepstakes before May 18, 2018.

Upside is announcing the launch of National Business Traveler Day (NBTD) to celebrate all those business travelers who schlep back and forth between work, home and hotels every month, every week or even every day.

In honor of the 2 million business trips that are taken every workday, Upside is holding a giveaway with some incredible prizes for NBTD, held on April 24. According to a release from Upside, NBTD will host “live celebrations” in airports around the country, featuring “thought leader events, non-profit partner tie-ins, and more.”

Upside was launched in January 2017 as an online travel agency offering discounts for business travelers. TPG’s JT Genter tested out the service and was able to save some serious cash with its travel packages.

The first giveaway is The Business Traveler Dream Sweepstakeswhich will feature a grand prize of “free first class upgrades for life.” What that really means is $5,000 per year (for 20 years) to cover the cost of domestic upgrades*, so no upgrades on long-haul international flights.

They’ll be giving out thousands of other prizes too, including the first prize of “free first class upgrades for a year” and two round-trip international business class tickets on United, which can be used on the carrier’s new Polaris business class.

The first prize winner will be announced on April 24 and the Grand Prize will be awarded once the sweepstakes closes in May. Enter to win and view the complete details here.

Upside is also unveiling a tournament-style bracket of the 32 Greatest Business trips in History. You can vote on what you think was the greatest work trip ever, from Paul Revere’s Midnight Ride to The Points Guy himself, Brian Kelly, who racked up enough points and miles to launch his business and career in travel. The entrant who most closely predicts the bracket outcome will win $5,000. Enter to win and view the complete details here.

If you sign up for the Upside through TPG, you can receive a free pair of Bose headphones after purchasing a trip package of $600 or more.

Featured image by American Airlines. 

*NO PURCHASE NECESSARY TO ENTER. Ends 11:59 PM ET on 5/18/18. Sweepstakes is open to legal residents of the 50 United States or District of Columbia, age 18 or older (or age of majority) who are employed by, own or are otherwise associated with a business entity and have traveled at least once on a business trip in 2017-2018. First Class Air Domestic Travel Upgrades for One Year paid as $5,000 cash. First Class Domestic Air Travel Upgrades for Life paid as $5,000.00 cash a year for 20 years. See Official Rules including sweepstakes periods, eligibility restrictions, prize details, conditions & limitations. Void where prohibited by law. Sponsor: The Upside Travel Company, LLC.
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More Things to Know
  • Receive 50,000 bonus points – a $500 value – after you make at least $3,000 in purchases in the first 90 days of account opening
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Intro APR on Purchases
N/A
Regular APR
17.74% - 24.74% Variable APR on purchases and balance transfers
Annual Fee
$95
Balance Transfer Fee
Either $10 or 3% of the amount of each transaction, whichever is greater.
Recommended Credit
Excellent/Good

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