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.
Delta SkyMiles® Platinum American Express Card

Earn 90,000 bonus miles and 10,000 Medallion® Qualification Miles (MQMs) after you spend $3,000 in purchases on your new card in the first three months of card membership. Offer ends 11/10/2021.

With Status Boost™, earn 10,000 Medallion Qualification Miles (MQMs) after you spend $25,000 in purchases on your Card in a calendar year, up to two times per year getting you closer to Medallion Status. Earn 3X Miles on Delta purchases and purchases made directly with hotels, 2X Miles at restaurants and at U.S. supermarkets and earn 1X Mile on all other eligible purchases. Terms Apply.

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More Things to Know
  • Limited Time Offer: Earn 90,000 Bonus Miles and 10,000 Medallion® Qualification Miles (MQMs) after you spend $3,000 in purchases on your new Card in your first 3 months. Offer expires 11/10/2021.
  • Earn up to 20,000 Medallion® Qualification Miles (MQMs) with Status Boost® per year. After you spend $25,000 in purchases on your Card in a calendar year, you can earn 10,000 MQMs two times per year, getting you closer to Medallion® Status. MQMs are used to determine Medallion® Status and are different than miles you earn toward flights.
  • Earn 3X Miles on Delta purchases and purchases made directly with hotels.
  • Earn 2X Miles at restaurants worldwide, including takeout and delivery and at U.S. supermarkets.
  • Earn 1X Miles on all other eligible purchases.
  • Receive a Domestic Main Cabin round-trip companion certificate each year upon renewal of your Card. *Payment of the government imposed taxes and fees of no more than $75 for roundtrip domestic flights (for itineraries with up to four flight segments) is required. Baggage charges and other restrictions apply. See terms and conditions for details.
  • Enjoy your first checked bag free on Delta flights.
  • Fee Credit for Global Entry or TSA Pre✓®.
  • Enjoy an exclusive rate of $39 per person per visit to enter the Delta Sky Club® for you and up to two guests when traveling on a Delta flight.
  • No Foreign Transaction Fees.
  • $250 Annual Fee.
  • Terms Apply.
  • See Rates & Fees
Regular APR
15.74%-24.74% Variable
Annual Fee
$250
Balance Transfer Fee
N/A
Recommended Credit
Excellent/Good
Terms and restrictions apply. See rates & fees.

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