Win A Free Trip

Travel took a hit in 2020, with Millennials and Gen Z-ers feeling some of the biggest impacts as they put sports, socializing and study abroad plans on hold during what should be the most explorative time in their lives. To make up for the lost year, CheapTickets® is giving one lucky 20-something an itinerary they can look forward to: win a free trip each year until they turn 30.

CheapTickets is giving away a trip a year to one lucky 20-something until they turn 30. Enter the brand’s “Travel in your 20s” contest Feb 22 – March 13 on their website. CheapTickets’ “Travel in Your 20s” contest winner will be awarded $5,000 in travel credits annually until they’re 30. The winner of CheapTickets’ “Travel in Your 20s” contest will be awarded $5,000 annually in travel credits until their 30th birthday that they can use to book a trip. Contestants have 20 days to enter the contest from February 22 – March 13, 2021 and must be between the ages of 20-29 to enter.

Entries to the “Travel in your 20s” contest will be judged by creativity, originality, quality and fit to theme based on answers to three essay questions. They are: What is the trip you most want to take before you turn 30 and why? If you win, how will you decide where to go every year? Put another way, what’s your 20s travel strategy? Would you rather, travel edition. Would you rather wake up in foreign country without your wallet or wake up without your passport or phone? Why? Responses are capped at 550 characters or less and participants are required to provide their name, age, address and email to enter. Based on the winners’ current age, the total prize is valued at up to $50,000.

To spark wanderlust inspiration, CheapTickets compiled a list of the most essential trips for every stage of your 20s, featuring 12 iconic destinations from around the world. Spring break spots such as Cabo’s Playa El Médano and South Florida top the list during students’ college years, while jet-setter favorites like New York and the Amalfi Coast are best for mid-20 travelers. Bucket list destinations, including Bali and Hawaii, round out the rankings as ultimate places to see before turning 30. 

Avid traveler and actress Ashley Tisdale has also teamed up with CheapTickets to share travel advice and memories from her 20s while encouraging fans and followers to enter the contest.  

CheapTickets is a budget travel site owned by Expedia Group, one of the world’s foremost travel companies. On and mobile apps, travelers search low-cost airfare, lodging, car rentals, activities, event tickets and cruises in one place and access best-in-class deals and discounts. College students and educators save more on travel every day when they verify their .edu address on to claim 18% off hotels.