The Perks and Perils of a Last-Minute Trip

My mom and I leave on Thursday for a long weekend trip to Chicago. We booked our flights just two weeks ago, and didn’t nail down our hotel reservations until last Friday night.

As someone who normally books a few months in advance — and starts planning and daydreaming about a trip long before that — I’ve found myself in the somewhat unfamiliar role of a last-minute traveler. Forget about spending weeks leafing through guidebooks, scouring hotel reviews and seeking out inspirational travel photos on Flickr in the slow build-up to a trip. Mom and I found a complementary gap in our busy schedules and jumped at it before the opportunity slipped away.

I’ve discovered that there are things to be said for the last-minute approach — as well as a few major drawbacks.

Pros:

1. There’s no danger of overscheduling ourselves. Mom and I have done enough research to pinpoint a few must-sees, but otherwise we’re going to keep our itinerary flexible and spontaneous.

2. We don’t have the torment of waiting months for a much-anticipated vacation. With a last-minute trip, you book, pack and go.

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Cons:

1. There’s no time to wait and track airfares in hopes that they’ll drop. The price of our flights jumped $50 a few days after we chose our travel dates — but with gas prices on the rise, I suspected we weren’t going to do any better, so I went ahead and booked. (Turns out I was right: The fares are now double what they were when I first started looking. So much for last-minute deals!)

2. Accommodation options are limited. By the time we got around to booking our hotel, a lot of interesting places were already sold out. All that was left in the affordable category were dive motels, a B&B with shared bathrooms and a few rental apartments in far-flung neighborhoods. (We went with option B.)

Do you enjoy getting away at the last minute, or do you prefer having a little more time to plan?