Travel Planning During Hurricane Season | What You Need to Know

When my best friend and I began planning our trip to Chicago nearly a year ago, we didn’t take one very important thing into consideration: hurricane season.

We set a date for September and carefully chose restaurants and activities — knowing that this would be my first visit to Chi-Town. Our plans included a sightseeing boat cruise, a Cubs game at Wrigley Field and much more.

The Atlantic Hurricane Season begins June 1st and ends November 30th. This Florida girl, born and raised, knows that some years are more active than others. 2017 is one of those years.

More than a week away from our trip, we began watching the forecasts for Hurricane Irma. My bestie lives on the east coast of Florida and I live on the west coast. We were both in the “cone of uncertainty,” meaning the storm could go either way.

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Luckily, both our communities were spared from serious damage, but not our trip. The day after Irma made a mess, Southwest Airlines cancelled our flights. Our options: book again within 14 days or receive a refund. We chose the latter.

Just days later, upon re-booking the flight to Midway Airport, the prices had significantly changed. To my surprise, I didn’t feel the #SouthwestHeart while on the phone with Customer Service.  The ticket to Chicago was still reasonably priced – and the same time as the original trip (score!); but the returning flight home to Tampa had increased in price by 200% for the same departure time.

I had to cut my sightseeing by nine hours so that I could stick to my budget. The one-way, evening flight now cost $400. Southwest’s representative made sure I was aware that I was paying the same price as my original flight, when I inquired why they wouldn’t price-match my ticket. I also made sure that she knew, that I had to be at the airport at 8 a.m. instead of 5 p.m. – because I had to reschedule a flight that they had cancelled.

  • Do your research. Always read an airline policy before booking. A cancellation may be imminent – and out of your control.
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Photo: Stroller Full of Fun

Unfortunately, we didn’t get to see the Chicago Cubs play at Wrigley Field, after all. We purchased tickets to a game weeks before our trip, but with the stress of hurricane cleanup and returning back to work, there was no time to sell them online. Our tickets were a total loss. We still visited Wrigleyville, but without hearing the crack of a bat.

  • Consider waiting until arrival before buying tickets for a show, sporting event or venue. Or you may have to re-sell the tickets online to get your money back, if your trip is cancelled.

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Prepare for a change of weather. This is probably one of the most important elements of vacation planning. Our jaunt to the Windy City was one month later than originally planned, and the weather didn’t disappoint. We experienced 36 hours of rain and chilly temperatures. I brought my umbrella with me, but left my rain boots at home. I can tell you after seeing a frenzy in the Nordstrom shoe department, the store was likely sold out of Hunter boots due to the gully washer and unprepared tourists.

  • Always check the weather — until the second you walk out the door. You never know what Mother Nature has in-store for you at your final destination. Ponchos and umbrellas are lightweight and much cheaper to buy at home.
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Photo: Stroller Full of Fun

What did I learn from our getaway? Planning vacations ahead of time doesn’t pay. Sometimes “Plan B” helps make the best memories. We were able to spend every second of our time in the city having fun.

This has been a devastating hurricane season. Not only were entire islands in the Caribbean wiped out – but some remain without power and food. Thousands of people are displaced. Towns will rebuild; cruise ships will return to their ports. Hurricane season once again proves to be unpredictable.

Did you ever experience a trip cancellation? Tell me about your tips — and how you handled it — on Facebook.