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Here are this week’s travel contests. You can win trips to Chicago, Illinois; Australia; Wales; a college football game; California wine country; a Celebrity cruise; New York City; Orlando, Florida; Los Angeles, California; Panama; and more.

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

Win a trip to Chicago, Illinois

  • Prize Details:
  • Flight cash to Chicago, Illinois
    Three-night stay in Ivy Hotel suite
    Daily complimentary breakfast for two
    Complimentary dinner for two
    Rose petal turndown on arrival day
    Charcuterie board on arrival day
    Bottle of bubbly on arrival day
  • open to all humans age 21 or older at time of entry. Residents of Taiwan, South Korea, Portugal, Italy, Austria, China, Russia, Hong Kong, Greece, France, Japan, Spain, and Czech Republic are not eligible to enter or win
    Enter by December 30, 2023

Win a trip to Australia

  • One (1) Grand Prize Package – One (1) seat on a 5-day, 4-night Kakadu’s Ancient Secrets tour. For tour details, visit: https://inspiringjourneys.com/kakadus-ancient-secrets/. Prize includes round-trip coach air transportation for winner from the major airport nearest the winner’s residence to Darwin International Airport.
  • Only open to legal residents of the United States (except Alaska & Hawaii) who are 18 years of age or older
  • Enter by December 31, 2023

Win a trip to Wales

  • Two (2) potential winners will each receive a prize consisting of a trip to visit Wales (the “Prize” or “Trip”). Trip includes round-trip economy class airfare for a winner and one (1) guest from a major international commercial airport near the winner’s home to a London airport, transfer to hotel accommodation in Wales and car rental during the trip. Trip has a maximum total budget of up to $5,000.00USD
  • open only to legal residents of the United States who are at least eighteen (18) years old or older
  • Enter by December 31, 2023

Win a trip to a college football game

  • A total of four (4) grand prizes will be available to be awarded (see grand prize drawing details below). Each grand prize consists of a trip for six (6) people (winner and five (5) guests each age 21 or older) to attend a 2024 regular season College Football game of the winner’s choice, from a list of available College Football games as designated and provided by Sponsor, based upon availability. Designated college football game must be a regular season game, played in the forty-eight (48) contiguous United States and excludes conference championship games, playoff games and bowl games.
  • Each grand prize includes: round trip coach airfare for six (6) people to designated airport serving the selected metro area of the selected game; hotel accommodations for six (6) people—three (3) rooms, double occupancy—for two (2) nights each; six (6) tickets to the designated regular season College Football game awarded either as electronic tickets (if a Dos Equis sponsored college football team) or $3,000 in Stubhub.com gift cards towards game tickets (note: availability of tickets to a particular game date and seat locations are not guaranteed); round trip transfers between the hotel and stadium for the game via the ground transportation as solely determined and designated by Sponsor based upon availability (i.e. mini bus, car service or Uber); $1,000 gift card towards tailgate party experience prior to and during game, from the gift card provider as solely determined and designated by Sponsor (gift card subject to the issuing gift card provider policy and terms and conditions of use); and $1,500 in Fanatics.com e-gift cards, towards any college football team gear for winner and guests (gift card subject to the terms and conditions of the Fanatics.com e-gift card policy terms and conditions).
  • open to all legal residents of the fifty (50) United States and the District of Columbia who are 21 years of age and older
  • Enter by December 31, 2023

Win a trip to California Wine Country

Win a Celebrity cruise

  • Win a Cruise With Points
    Enter the Cruise With Points Sweepstakes by December 31, 2023 for your chance to win one of two incredible prizes:
    (1) Grand Prize: A Celebrity cruise for two + 100,000 Marriott Bonvoy™ Points ($5,750 value)
    (2) First Prizes: 50,000 Marriott Bonvoy™ Points ($625 value)
  • open only to legal U.S.A residents currently residing in the 50 United States and the District of Columbia, who are 21 years of age or older
  • Enter by December 31, 2023

Win a trip to New York City (no donation required)

Win a trip to Orlando, Florida

  • *Grand prize includes:
  • Roundtrip airfare to Orlando
  • Transportation between the airport and hotel in Orlando
  • Hotel accommodations at Universal’s Cabana Bay Beach Resort
  • Admission to both Universal Studios Florida and Universal Islands of Adventure theme parks, plus Universal Volcano Bay water theme park
  • only open to permanent legal residents of the fifty (50) states of the United States (“U.S.”) and the District of Columbia (“D.C.”)
  • Enter by December 31, 2023

Win a trip to Los Angeles, California (no donation required)

  • 2 VIP prime orchestra tickets to the 75th Emmy® Awards
  • Exclusive access to a post-Emmys celebration
  • Special red carpet photo opportunity
  • Roundtrip airfare for 2 to Los Angeles, CA
  • Hotel accommodation for 2 nights
  • Open worldwide
  • Enter by January 1, 2024

Win a stay in Panama (does not include airfare)

  • You could win a 5-night all-inclusive stay for two at Los Establos Boutique Resort, Panama. Included in the prize are all meals, beverages and activities.
  • open to anyone who is at least eighteen (18) years of age and has reached the age of majority in their jurisdiction of residence at the time of opt-in (19 in Alabama and Nebraska; 21 in Mississippi) and a resident of the United States of America and the District of Columbia (excluding residents of Alaska, Hawaii, Rhode Island, overseas military installations, Puerto Rico, and other U.S. Territories)
  • Enter by January 3, 2024

Go on an adventure at home or when you’re away with a tour or activity via Get Your Guide.

Which travel giveaway are you most excited about winning this week?

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!

Hi, I'm Jonathan, the traveler, writer, photographer, enthusiast, & terrible dancer of Everybody Hates A Tourist with decades of travel expertise. I've visited over 40 countries so far. Join me as I share my personal experiences finding the best food, craft beer, cocktails & spirits, wine, culture, & history around the world!

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