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Here are your travel contests for this week. You can win trips to New York City; Los Angeles, California; Costa Rica; Oahu, Hawaii; Dubrovnik, Croatia; and more.

Good luck & be sure to subscribe to the weekly newsletter so you don’t miss any contests and please share this post with friends who might take you along if they win!

Win a dream vacation

  • $2,000 towards a trip of YOUR choice from
  • $450 to spend on your trip from Chillbo & Dollar Flight Club
  • $250 worth of travel gear from Chillbo
  • Enter by September 23, 2018

Win a trip to New York City

Book your hotel in Travel Contests - Win A Free Trip! now!

  • One (1) Winner will receive one (1) $1,000 shopping spree from, in the form of a gift card (ARV: $1,000), two (2) VIP tickets to PRETTY
    WOMAN: The Musical, including, subject to availability, a cast meet & greet and autographed
    memorabilia (ARV: $700), round-trip coach air transportation for two (2) on American Airlines
    (Terms and Conditions apply) from a major airport closest to the Winner’s residence served by
    American to New York, NY (ARV: up to $1,500) and hotel accommodations (standard
    accommodations, one room with double occupancy) for Winner and guest for three (3) days, two
    (2) nights at the Langham Hotel Fifth Avenue (ARV: $1,800)
  • Enter by September 24, 2018

Win a trip to Los Angeles, California

  • $1000 Airfare Voucher
    $1000 Credit for Luxury Hotel Stay
    $500 Gift Card towards Merrell Apparel
    $500 Spending Credit for Restaurants and Transportation
    2 Tickets to Tough Mudder Full or Half
    $150 Worth of Product from
  • Read about the best craft beer in downtown Los Angeles
  • Enter by September 25, 2018

Win a trip to Santa Monica, California

  • – 3-day, 2-night stay at Shutters on the Beach in Santa Monica, California.
    – 3 limited-edition pieces from the goop x Lilly Pulitzer collaboration, featuring shift dresses, maxis, a beach bag, and more.
    – A 1-year subscription to the POPSUGAR Must Have box, bundled with full-size beauty, fashion, and home products, plus more surprises.
  • – $250 airline credit
  • Enter by September 27, 2018

Win a trip to New York City

  • $500 AMEX gift card for travel
    3 nights at the Freehand NYC
    A private tour of Rosé Mansion with the founders for 8 people
    3L bottle of Rosé in the bar with snacks
    All 8 people get a t-shirt and a tote bag
    Surkus Experience Package: $150 gift card for event of choosing + more
  • Enter by September 27, 2018

Win a trip to Costa Rica

  • • $500 towards travel expenses from Newser and Kitchn
  • • 2-lifetime subscriptions to Journo, $498 value
  • • 3-night stay for two at Finca Luna Nueva courtesy of Regenerative Resorts in Costa Rica
  • • All meals and a property tour are included
  • Enter by September 28, 2018

Win a trip to Oahu, Hawaii

  • One (1) Grand Prize, consisting of a five (5) day/four (4) night trip for the winner and three (3) guests to Honolulu, Hawaii [awarded in the form of a Delta Vacations Certificate (“Certificate”)]. Trip includes roundtrip main cabin air transportation from the major airport nearest winner’s home serviced by Delta Air Lines (in Sponsor’s sole discretion) to Honolulu, Hawaii (Certificate is redeemable for up to $1,200 towards air transportation per person), four (4) nights’ hotel accommodations [one (1) room/quadruple occupancy] at a participating Delta Vacations hotel
  • Enter by September 28, 2018

Win a trip to Dubrovnik, Croatia

  • $1000 Airfare Voucher
    5 nights, 4 days Dubrovnik Hotel
    Delicious Daily Breakfast
    Dubrovnik City Tour of city walls, castles, & fortresses
    Day Trip to beautiful Kotor, Montenegro
    Medieval Fine dining experience
    $500 Cole Haan gift card
  • Enter by September 29, 2018

Why not share this post with your friends? If they win, maybe they’ll take you!

Want to see the newest travel contests? Go here!

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