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Here are your travel contests for this week. You can win trips to Lollapalooza in Chicago, Illinois; Los Angeles, California; Miami, Florida; Aruba; San Diego, California; a staycation; Costa Rica; New York City; and more.

Good luck & be sure to subscribe to the weekly newsletter so you don’t miss any contests!

Win a trip to Lollapalooza in Chicago, Illinois

  • One (1) Grand Prize will be awarded, which will consist of a 6-day/5-night trip for winner and one guest to Chicago, IL from August 2, 2017 through August 7, 2017 to attend each day of the Lollapalooza music festival. The trip will include round-trip coach class air transportation from a major airport near the winner’s home city to Chicago, IL, five-night hotel accommodations (based on double occupancy and availability), and two (2) general admission tickets to each of the four (4) days of Lollapalooza from August 3, 2017 through August 6, 2017
  • Enter by July 5, 2017

Win a trip to Los Angeles, California

  • Two FYF Fest tickets
    Three nights at the Freehand Downtown LA
    $500 travel voucher
    $500 shopping spree with Azalea
    $250 shopping spree courtesy Hudson Jeans
    Three months of Wine Awesomeness
  • Enter by July 5, 2017

Win a trip to Miami, Florida

  • $750 Trip Cash for a two-night stay in South Beach Miami from The Guestbook
    $200 Travel Cash compliments of
    $200 Flight Voucher from Sole Serum
    3-month subscription to Curos
    $150 to select wine of your choice from Mash + Grape
  • Enter by July 8, 2017

Win a trip to Aruba

  • • A 5-night stay for two in an Oceanfront room at the new Tamarijn Aruba All Inclusive – Set travel dates of Wednesday, August 23 – Monday, August 28, 2017
    • 10 Restaurants and grills
    • 8 Bars with daily drink specials
    • 4 Freshwater pools
    • Non-motorized water sports
    • Daily activities and nightly entertainment
    • Free Wi-FI
    • Roundtrip airfare including airport transfers to and from the hotel in Aruba
  • Enter by July 10, 2017

Win a trip to San Diego, California

  • $1,000 gift card towards round trip flights for two
    3 Nights accommodations
    Tour of Stone Brewing Co.
    Dinner for 2 at a delicious local restaurant (TBD)
    $200 of Uber credits
  • Enter by July 10, 2017

Win a staycation

  • Home Automation Starter Package from Smarthome ($500 value)
    $500 of travel cash from The Guestbook
    6 months of wine exploration with Wine Awesomeness
    Custom Color Sheets from Flaneur ($500 value)
    $250 AMEX gift card to splurge from Dering Hall
    $250 Amazon gift card for lounging supplies courtesy of Red Tricycle
  • Enter by July 10, 2017

Win a trip to Costa Rica

  • $500 towards airfare.
    A spot on Have Fun Do Good’s social good group trip to Costa Rica from November 8-12, 2017.
    Accommodation right in the heart of Tamarindo in a 5BR / 6BA penthouse.
    Airport shuttle, food, a rad t-shirt, activities, and the chance to volunteer with some amazing organizations.
    $150 shopping spree to Sol De Janeiro for beach-ready beauty products.
    A case of Curious Elixirs booze-free craft cocktails.
  • Enter by July 12, 2017

Win a trip to New York City

  • Two (2) Night Stay at Hotel 50 Bowery (ARV $1385)
  • Welcome Cocktails for two (2) (ARV $42)
  • Mini-bar Credit (ARV $50)
  • Breakfast for two (2) daily (ARV $248)
  • Free passes for two (2) to nearby Museum of Chinese in America (MOCA) (ARV $20)
  • $600 to go towards suiting at the Todd Snyder Madison Square Park Flagship Store (ARV $600)
  • Choice of show for two (2) at Brooklyn Bowl and the Capitol Theatre (ARV $150)
  • $500 prepaid Mastercard for travel (ARV $500)
  • $200 prepaid Mastercard for food (ARV $200)
  • Enter by July 12, 2017

Want to see the newest travel contests? Go here!

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