General Travel Tips

Why We Fly Southwest to Orlando Every Time

Finding flights is often the most stressful part of planning a trip, and unfortunately it’s not something most travel agents will help with because airlines don’t pay a travel agent commission. Booking can be time consuming, flying is expensive and there are so many choices! I’m here to tell you what my husband and I do and why we do it in the hopes that it will ease your stress and fears.

We always fly Southwest. Always. Whether we’re going to Orlando and heading to Disney or we’re going to Philly to visit my parents. We only started flying Southwest when we got married. Growing up, my family was never loyal to one airline; We flew whoever had cheap flights at decent times. My husband’s family didn’t do much air travel. But man, hubby and I love flying Southwest!


For better or for worse, we aren’t super close to any airports where we live, so we have lots of choices because they’re all about two hours away. We fly out of Boston, MA; Manchester, NH; Hartford, CT; or Albany, NY depending on who has direct flights at reasonable times for decent prices.

But our top 3 (and a half) reasons for always flying Southwest?

  1. The best prices. We have yet to find another airline that consistently offers direct flights out of our choices of airports at affordable prices.
  2. Two free checked bags. I’ll go into this more. It’s such a fabulous perk.
  3. Wonderful Flight Attendants. They always make us laugh and are so attentive.
  4. aka 3.5 because it doesn’t quite apply to us yet, but I know it’ll be a huge perk in the future: Family Boarding. I’ll go into more detail on this too =)

Why do we EACH need two checked bags AND a carry on bag AND a personal item? I mean, NEED is a strong word, but we’ve loved being able to have all of this luggage, especially for Disney. Our second checked bag is usually mostly empty on the way down and we fill it with souvenirs on our way home! It’s also great for dirty laundry on long trips. But mostly, it’s great not to have to stress. I can pack a few extra pairs of shoes and a few extra outfits without worrying about space or weight.

Many people find Southwest’s open seating to be stressful. I personally love it. When you book your ticket, you are not assigned a seat. You have to check into your flight 24 hours before your departure time and you’ll be assigned a boarding group (A, B or C). We’ve boarded in group C, having forgotten to check in until about 3 hours before the flight, and still been able to sit next to each other.  For families, I know this can be extra stressful which is why I mentioned Family Boarding. Families with children 6 years old or younger can board after Group A, before Group B, no matter which group they’re assigned at check in. This way there is no stress about parents sitting with young children!

Obviously you can fly with any airline you like, and you may very well find better prices than Southwest. Maybe Southwest doesn’t even fly out of your airport! But if you’re looking for a recommendation based on personal experience, we LOVE Southwest!

A tip I’ve learned for booking flights: the cheapest flights are midweek. If you can fly on a Wednesday, you’ll get great deals. Doing your actual booking of your flight on a Tuesday six to eight weeks before your trip will also find you some great prices.

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P.S. Southwest hasn’t paid me to write this review. I just honestly love them. Maybe someday they’ll pay me 😉

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