This Week is the BEST Time to Book Holiday Travel and Flights

Summer may be winding down and you may have backyard BBQs on the brain, but it’s time to start thinking about your holiday travel plans. In fact, this week (Aug. 10 – Aug. 16, 2015) is THE best week to book December flights, according to a study by Skyscanner.

When to Book Your Holiday Travel

The next best time to book your holiday travel is the week of Sept. 28, when you can save around 9.1 percent. No matter what, you should purchase your flights no later than the week of Nov. 2 because that’s when you’ll save 4.76 percent.

You probably already know this, but if you plan a trip for the week of Christmas to New Year’s Eve, you’re going to pay a premium. But you might not realize that there’s usually a sweet spot in the second to third week of December, right before Christmas. So if you’ve been waiting to go on that la jolla kayak cave tour, right around now would be the best time to get your bookings done!

Also, you can usually score the best deals on flights if you travel on a Tuesday or a Wednesday. Fares are typically higher Friday through Sunday. But if you can be a little flexible, then you can book some major deals! Typically fares reach their lowest point somewhere between 27 and 114 days out and this is considered the prime booking window. Just do a quick research and plan your itinerary based on that. For instance, if you were to plan and travel to Dallas, you might come across a number of options that you can explore. From hopping bars in Dallas to exploring cultural activities and attending symphony concerts, there are many things you can add to your checklist. But, it requires thorough planning. You need to book the tickets well in advance and stay at least 3-4 days and explore the city.

I like to use Southwest’s search mechanism to look for for lowest fares by month. Other airlines will run specials that look like a “deal” but once you get to the checkout page, they’ve tacked on a bunch of extra fees. One airline I researched (which will remain nameless, at least for now) even charged an extra $12 to book a seat — not a special seat, but A SEAT.

I’m not sponsored by Southwest (hello, I should be!), but I like how they thumb their noses at the rest of the airline industry when it comes to making customers happy and not charging extra fees for bags. Plus, it’s cheaper for me to fly Southwest with my dog ($75 one way, instead of $150 on some airlines. UPDATE: Southwest bumped their pet fee up to $95. Boooooooo.). But seriously, why should it be a pain to sort going on holiday with your pet? It shouldn’t have to be!

I would take my dog everywhere if I could. However, to begin considering such an option, you would have to take into account multiple questions such as ‘should they be left in the car for too long?’ or ‘how much would it cost to take your pet along with you?’ and do adequate research on the same before taking a decision. Multiple factors come into play at times such as this. In fact, my friend told me he likes to go to the Big Bear destination once a year for a holiday, and they have a selection of big bear pet friendly cabins there so he can take his dog with him! It would just be great if there was more around.

Since I’m obsessed with the Sunshine State, that’s the destination we’re going to focus on today.

Okay, so let’s look at your travel options. I researched Southwest’s December flights from Kansas City, Dallas and Chicago into Tampa, Fort Lauderdale and Orlando. Beaches and sunshine here we come!

First for my Kansas City friends (my hometown!):

Kansas City to Tampa: Fares are pretty steady for the first half of the month and bottom out at $183 one way. The worst days to fly are Saturday, Dec. 26, Sunday, Dec. 27 and Monday, Dec. 28 ($332).


Kansas City to Fort Lauderdale: Wow, you can score a deal for as low as $138 one way. But, Sunday Dec. 27 is still the worst day to fly (a whopping $431).


Kansas City to Orlando: Book a flight for as little as $151. Both Dec. 26th and the 27th soar to $335.


Next, let’s look at Dallas:

Dallas to Tampa: That $79 fare in December is burning a whole in your pocket. Book it! Fares go up to the $129-$294 range later in the month.


Dallas to Fort Lauderdale: $69 baby! But it’s hiking up to $371 on Dec. 26- 27.


Dallas to Orlando: $84 ain’t bad, but you don’t have too many options. Just watch out for those triple deuce digits between Christmas and NYE.


And last, but not least, Chicago!

Chicago to Tampa: You’re escaping that COLD Chi-Town weather for as low as $94 if you fly out on Dec. 1, 2 or 5. Otherwise those flights are going up.


Chicago to Fort Lauderdale: $79 woot woot! And there are few opportunities to score a $107 flight there and back!


Chicago to Orlando: $70, say what!? That return flight is going to cost you, unless you get back to the Windy City on Thurs. Dec. 17 for $105.


Now It’s Time to Pick a Hotel

Where to Stay in the Tampa Bay Area

One of my favorite resorts in the area is the Loews Don CeSar Hotel in St. Pete Beach. It’s located directly on a gorgeous stretch of white sand and the hotel looks like a giant pink sandcastle. Hence we like to call it the Pink Palace. When you book directly through the Loews website, they’ll match any rate you find on another site. I pulled their rates for three different weeks in December and these are the lowest rates I found based on a seven-night stay:

  • Tues. Dec. 8 – Tues. Dec. 15: $188 per night.
  • Tues. Dec. 15 – Tues. Dec. 22: $170 per night.
  • Tues. Dec. 22 – Tues. Dec. 27: $269 per night.


Where to Stay in Fort Lauderdale

I looked at both the W Hotel Fort Lauderdale and The Ritz-Carlton Fort Lauderdale. The W is great for a romantic trip for two or for a younger crowd that wants to enjoy a little nightlife action on the beach. The Ritz is a better option for families. I know what you’re thinking — here I am talking about deals and I’m also recommending a super luxe hotel. Hold on to your horses! Yes, the prices at the Ritz soar into the $800s the closer you get to Christmas. BUT, you can score a killer deal Dec. 7 – 14 ($370 per night). That’s THE RITZ, people.

Here’s the breakdown for the W…

  • Tues. Dec. 8 – Tues. Dec. 15: $376 per night
  • Tues. Dec. 15 – Tues. Dec. 22: $359 per night
  • Tues. Dec. 22 – Tues. Dec. 27: $446 per night


Where to Stay in Orlando

One of my favorite places to stay in Orlando is the JW Marriott at Grande Lakes. It’s especially great for families — there’s a pretty sweet lazy river, transportation to the theme parks and the restaurants on site are amazing. I had to average the prices over a seven-night period because on the website, each night is priced separately. Bonus: when you book directly through Marriott, if you find a lower available rate, they’ll match it + give you 25 percent off.

  • Tues. Dec. 8 – Tues. Dec. 15: $289 per night
  • Tues. Dec. 15 – Tues. Dec. 22 $220 per night
  • Tues. Dec. 22 – Tues. Dec. 27 $270 per night (that’s less than Dec. 8 – Dec. 15!)


These prices aren’t going to last. So what are you waiting for? Book your trip to the fun and sun! And then when I’m posting my beach photos on Instagram in December, you’ll be doing the same thing.

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