Are you struggling to come up with an awesome Valentine’s Day plan for you and your main squeeze? Dinner and a movie sounding like a bit of a snooze? There’s nothing like a little surprise weekend getaway to dial up the romance.

Valentine's Day Travel: A Round-Up of Helpful Tips and Suggestions

This year V-Day is on the weekend too – so that’s convenient! Here are a few last minute romantic destinations you can still book airfare for a reasonable-ish rate.

If getting out of town is too much of a hassle, do not discount the idea of the staycation. Sometimes all that’s needed for a little romance reboot is the perception that you’re on holiday. Allow us to share some staycation accommodation and dining inspiration in spades if Boston, Los Angeles, San Francisco, Chicago or New York are your hometowns. But even if you live in a destination we haven’t profiled, we strongly urge you to visit your hometown like you’re on your honeymoon. And then report back to us – we guarantee it’s a winning strategy!

Here’s one last completely out-of-the-box Valentine’s Day idea to ponder. Give your honey the gift of travel on Valentine’s Day, but do your actual traveling later in the month. Our rationale is pretty straight-forward. Demand always drives up airline ticket prices. This year, Valentine’s Day is on the weekend (also, notoriously an expensive time to fly) [include links to post]. Tickets that will cost you $400 and $500/per person to book for the holiday weekend, are substantially cheaper if you just wait until the following week.

For example, flying to New York City from Chicago over Valentine’s weekend will cost $100 per ticket more than just waiting a week. If you fancy a visit to the Space Needle in Seattle and you’re flying in from Los Angeles you can prepare to pay almost $400 an airline ticket for the privilege over the holiday weekend. The same itinerary is almost half off if you simple book the following weekend at $205 a ticket (Friday, February 20 to Sunday, February 22). Need another reason to avoid Valentine’s Day? How about the long waits for a table at most restaurants. Nope, for our money the most romantic move might be to stay in, snuggle by the fire and defer that costly weekend out-of-town – just for a little while. And what’s more romantic than having a little bit more money in your pocket to spend on your partner in crime?


  1. Hi cheapair, I would love to know about info of traveling to England for next month and I wanna know how long should I book the air ticket before I leave ?

    • Hi Vira, I assume you are planning a trip from the U.S. I would suggest booking now. There’s no upside to waiting as we are very close to travel and prices will only go up. Good luck to you!

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