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If you’re a regular TPG reader, you’d pretty much have to be flying without Wi-Fi this month to have missed our posts about Pride month, and all the incredible giveaways we’ve arranged to celebrate the occasion — like your chance to win the Trip of a Lifetime planned by The Points Guy using up to 1 million Chase Ultimate Rewards points.

CLICK HERE TO ENTER TO WIN: $10 minimum donation

That grand prize includes a trip to New York City to plan the ultimate trip of your dreams, with the help of The Points Guy himself, Brian Kelly.

But just to up the fun factor, we’re also offering additional incentives in the form of flash sweepstakes. Our next big prize is two VIP tickets to comedian Claudia Oshry’s Dirty Jeans Tour, which include a private meet-and-greet opportunity with the original Girl With No Job, and are valid for any location on the tour. (Travel and accommodations are not included.)

Not sure when she’s coming to town? Upcoming show locations include:

  • June 25 in Minneapolis, Minnesota — The Assembly, 7pm
  • June 26 in Lexington, Kentucky — Comedy Off Broadway, 7:15pm
  • July 26 in Charleston, South Carolina — Charleston Music Hall, 8pm
  • Aug. 14 in Virginia Beach, Virginia — Funny Bone, 7pm
  • Aug. 15 in Richmond, Virginia — The National, 8pm
  • Aug. 17 in Asbury Park, New Jersey — Paramount Theatre, 9pm
  • Sept. 1 in Las Vegas, Nevada — Terry Fator at Mirage, 10pm
  • Sept. 13 in Austin, Texas — Paramount Theater, 8pm
  • Sept. 19 in Portland, Oregon — Alladdin Theatre, 8pm
  • Sept. 20 in Seattle, Washington — Nordstrom Theatre, 8pm
  • Sept. 22 in Vancouver, British Columbia — The Vogue Theatre, 8pm
  • Oct. 5 in Chicago, Illinois — The Vic Theatre, 7:30pm and 10pm
  • Oct. 6 in Milwaukee, Wisconsin — Turner Hall, 7pm
  • Oct. 13 in Los Angeles, California — Theatre at ACE Hotel, 8pm
  • Oct. 18 in San Diego, California — Balboa Theatre, 8pm
  • Oct. 20 in San Francisco, California — Regency Ballroom, 5pm and 8:30pm
  • Nov. 2 in Toronto, Ontario — Queen Elizabeth Theatre, 8:30pm
  • Nov. 16 in Pittsburgh, Pennsylvania — Roxian Theater, 7pm
  • Nov. 17 in Philadelphia, Pennsylvania — The Fillmore, 8pm
  • Nov. 22 in New Orleans, Louisiana — Civic Theatre, 8pm
  • Jan. 25, 2020 in New York City, New York — Beacon Theatre, 8pm

Only on Monday, June 24, every single donation to TPG’s Rainbow Railroad Prizeo campaign includes automatic entry into the Dirty Jeans Tour Flash Sweepstakes.

So, here’s how you can enter for a chance to make this flash sweeps package your own. Make a donation of $10 or more to TPG’s Rainbow Railroad Prizeo campaign on Monday, June 24, before midnight. Donations made today will automatically enter you into the Dirty Jeans Tour Flash Sweepstakes, in addition to our massive giveaway: The Trip of a Lifetime planned by The Points Guy using up to 1 million Chase Ultimate Rewards points.

The Dirty Jeans Tour Flash Sweepstakes ends at 11:59pm ET on Monday, June 24 — so get those donations in now to qualify.

CLICK HERE TO ENTER TO WIN: $10 minimum donation

Featured photo courtesy of Claudia Oshry/Girl With No Job.

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Chase Sapphire Preferred® Card



CARD HIGHLIGHTS: 2X points on all travel and dining, points transferrable to over a dozen travel partners

*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 60,000 bonus points after you spend $4,000 on purchases in the first 3 months from account opening. That's $750 toward travel when you redeem through Chase Ultimate Rewards®
  • 2X points on travel and dining at restaurants worldwide & 1 point per dollar spent on all other purchases.
  • Get 25% more value when you redeem for airfare, hotels, car rentals and cruises through Chase Ultimate Rewards. For example, 60,000 points are worth $750 toward travel
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