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: a free trip each year until they turn 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 on CheapTickets.com1. 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.

“The pandemic has halted our travel plans and many 20-somethings have missed out on valuable time to broaden their horizons,” says Justine McDonald, Senior Brand Manager at CheapTickets. “In a survey we conducted last year, more than half of college students reported that they have not traveled since the start of COVID-19 in March 2020, and 40% said they didn’t know when they’d feel comfortable traveling again. That’s why we’re giving young travelers years of free trips to look forward to.”

Travel in Your 20s Contest Guidelines
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.

20s Travel Inspiration 
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.

“After experiencing a year without travel, I think people, especially those in their 20s, have a deeper appreciation for new experiences, growth and seeking out all that there is to do and see in the world,” says Tisdale. “In my 20s, I made so many amazing memories shooting movies, touring and pursuing my career. But some of my favorite places – like Spain, Cabo and Italy – are destinations I explored on my own and with people I love. I don’t think there’s anything that leads to growth as much as travel.”

For updates on the Travel in Your 20s contest, follow @CheapTickets on Instagram or visit to enter. Students can also save on future travel by verifying their .edu email address on for 18% off hotels year-round.

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. For more ways to save and earn rewards when travelers refer their friends, visit CheapTickets – where the best trips in life are cheap.

© 2021, Trip Network, Inc., an Expedia Group Company. All rights reserved. CheapTickets,, and the CheapTickets logo are either registered trademarks or trademarks of Trip Network, Inc. in the U.S. and/or other countries.

1 See for complete list of terms and conditions for Travel in Your 20’s contest.