Win Airfare to ???: The Solo and Spontaneous Contest

Solo Traveler has partnered with Skyscanner, a leading global travel search site, for our Solo and Spontaneous FREE airfare contest.

This is exciting news for readers of the Solo Traveler Newsletter.

If you travel solo and you’re spontaneous, you’re ready to win your airfare to ??? with The Skyscanner Solo and Spontaneous “Cheapest Flight to Everywhere” Contest.

It’s like going to the airport and saying “give me the cheapest ticket to anywhere”. Except you book online, you have a bit of time to plan and the flight is paid for you (up to a value of $300).

There will be three winners over three months:

  • November
  • December
  • January.

How did this come about? The contest was cooked up at the TBU travel blogging conference last month where I met Julie from Skyscanner. She told me about their “Cheapest Flight to Everywhere” button on their booking site and we came up with this contest.

The Solo and Spontaneous “Cheapest Flight to Everywhere” Contest.

As a solo traveler, I’ve learned that I can have a great time just about anywhere. And sometimes just anywhere is where I want to go.

Rather than going on a booking site and searching various destinations for one I can afford, on Skyscanner, I can enter my home airport, hit their “Everywhere” button and it will produce a list of destinations in order from least expensive to most. How cool is that!

I just tested the system and, if I was to win today, I’d be flying off to Quebec City. Tomorrow it could be New York or North Bay, Ontario. One never knows where this button could take you. That’s the fun of it. And, as I’ve written about before, small town travel can be as exciting as big city – so just anywhere can be great!

Here’s how the contest works:

  • 1st Monday of the month – The Solo Traveler Newsletter will go out on the first Monday of each month. The link to enter is in the newsletter.
  • Following Wednesday – You have until Wednesday at midnight ET to enter the contest.
  • On the Thursday – The winner will be announced on the Solo Travel Society Facebook page the Thursday of the same week. I’ll email the winner directly.
  • Next 2 weeks – You must travel within the next 2 weeks – so you have two weekends to make your trip.
  • One more week – You must complete a form (similar to the Destination of the Week posts) and provide some details about your trip and a few photos so that we can share it on Solo Traveler.

Here’s how to win

  • To qualify, you must be a recipient of the Solo Traveler Newsletter. If you’re not signed up, you can do so here. Watch for your confirmation email to complete your sign-up.

  • Watch for the Newsletter in your inbox on the first Monday of the month.
  • Enter the contest immediately. Don’t postpone as the winner will be determined just two days later at midnight Eastern Time.
  • Be ready for a weekend or midweek getaway. If you win, you must travel within 2 weeks.

These conditions apply

We kept these to a minimum:

  1. Entrants must be 18 years of age or older.
  2. The competition will be open for 1 week, with the deadline for entries being clearly stated on the Solo Traveler Newsletter. Entries after this closing date will not be eligible to win.
  3. The winning entry will be awarded a flight up to the value of $300 (or GBP/EURO equivalent based on current exchange rates) found on Skyscanner.
  4. Skyscanner will book the flight on behalf of the winner, and will do so within 2 working days of receiving all relevant passenger information.
  5. The winner must be able to use their winning flight within 2 weeks of the prize being awarded.
  6. Accommodation, any extra activities and costs beyond the specified prize are the responsibility of the winner.
  7. The winner agrees to share their experience of their trip on Solo Traveler within the month of winning the prize.
  8. By accepting this prize, the winner accepts full and complete responsibility for their own safety and welfare at all times, including familiarizing themselves with and arranging for passport, visa and other travel requirements.
  9. The prizes are non-transferable and no cash alternative will be given. The value of the flight may not be used as a credit on any other flight.
  10. Contest is open to people of all nationalities unless prohibited by law.
  11. By entering this competition, entrants accept the terms and conditions listed above.

Good luck!

Fingers crossed. I hope you win!


Our first winner was Rachel W. of Spain. She flew to…drumroll please…Norway! Oslo, to be precise. Watch for a post soon where she shares her experience there. Congratulations Rachel.


  • Janice Waugh

    It’s the two weeks following the selection of the winner. Good luck!

  • Lynette

    Is it any 2 weeks, or the 2 weeks immediately upon winning the trip that the travel needs to commence? I work a full-time job and can’t take off until spring break or summer. I would like to travel but am limited on the time-frame.

  • Jdyhfnr

    I don’t seem to be getting the newsletter even though I get a message saying I am signed up.

  • Janice Waugh

    Hi there, Yes, the post indicates that we would announce the winner of the Solo Travel Society on Facebook. We did and the winner is Rachel of Spain who is going to Oslo this weekend. Thanks for checking in.

  • mlc.intl

    I entered this contest and have received every email/newsletter there after. However, I was unable to see who the winner of this contest was/is? I checked on the first Monday of the month as instructed, and almost everyday there after. Maybe I am doing something wrong or looking in the wrong place?

  • Tracy Antonioli

    I’m in, too. I love being spontaneous! And I’d love to do a quick getaway. It’s been three months since my last trip–I’m overdue!

  • Rachel

    Sounds fun to me – I´m in.

  • Jamie

    I’m excited any getaway is welcomed.

  • Joyce

    ANY getaway for me would be fun! Even just for 24 hours!

  • Janice Waugh

    A weekend getaway can be fun too!

  • Travelbug1

    This sounds OK …….. BUT if I wanted to stay somewhere a day or two longer I have to get approval of holidays @ work and sometimes last minute approvals are hard to get. That sucks :( Oh well, good for those that can do this!