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.
American Express® Green Card

WELCOME OFFER: 30,000 Points

TPG'S BONUS VALUATION*: $600

CARD HIGHLIGHTS: up to $100 annual CLEAR statement credit, up to $100 annual LoungeBuddy statement credit, 3x points on travel and transit, 3x points on restaurants worldwide

*Bonus value is an estimated value calculated by TPG and not the card issuer. View our latest valuations here.

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More Things to Know
  • Earn 30,000 Membership Rewards® points after you spend $2,000 on purchases on your new Card in your first 3 months.
  • Earn 3X Membership Rewards® points on all eligible travel, from subway swipes and window seats to hotel stays and city tours.
  • Earn 3X Membership Rewards® points at restaurants worldwide.
  • Receive up to $100 per year in statement credits when you use the American Express® Green Card to pay for your CLEAR® membership at select airports and stadiums across the U.S. and Permissible Biometric Scanning Technology terms: eye scanning, irises scanning and fingerprints scanning.
  • Use the American Express® Green Card to purchase lounge access through LoungeBuddy to any of the lounges in the LoungeBuddy network – no memberships, elite statuses, or first class tickets required. Earn up to $100 in statement credits per calendar year on your LoungeBuddy purchases.
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