How To Travel In A Safe And Wise Way (What I Learned From The Southwest Failure)

I was apart of the horrible Southwest cancellations in late December. And when I say horrible, I mean horrible.

We were set to fly back on the 26th from Phoenix to Milwaukee with a quick layover in Denver. We got to Phoenix and both flights were on time. We were feeling great. But things started to shift during our hour-long layover in Denver. Right when we were set to board our next flight, they told us our crew had not even taken off from Chicago yet. After 6 hours of waiting, they eventually cancelled our flight. In a last minute scramble to get a new flight we found one on Southwest for the next day at 6 am. This meant we had to get a hotel in Denver, Uber to Downtown, and get some clothes and toiletries since our bags were not given back to us. We just accepted the situation at this point and that we would get out the next day.

Later that night, we checked and noticed (without any warning from Southwest) that our flight again was cancelled. We scrambled to find any available flight and luckily got on one with United but had to go to Midway instead of Milwaukee (for almost $800). My brother in law was nice enough to pick us up and drive us to Milwaukee so we could grab our car and bags. When we get there, our bags were still not there. They said they were still in Denver and we will eventually get them back. Now 2 weeks later, we finally got our bags back (just yesterday).

I learned a lot from this experience on how to travel safely and wanted to share some takeaways with you guys so you can avoid this.

1. Only Check The Bags You Need To Check

With Southwest, it is easy to choose to just check all bags so you do not have to walk with them as they are free. But as you can see, this does not always work for you. Check the big bag that you need to check, but then carry on the rest of your bags and make sure you have a few outfits to wear just in case.

2. Get Air tags For Your Luggage

For days after we arrived, we had to keep going back to Milwaukee Airport to see if our bags were there. No one had any clue really where they were. Spending $25-$30 on Airtags so you know where they are is a no brainer. If anything, it will give you some peace of mind.

3. Avoid Connecting Flights Whenever You Can

It is no secret that connecting flights leads to more problems. It may be worth spending a little extra to avoid this to ensure you get to your destination on time! I know after this experience, I am no longer doing any connecting flights.

4. Always Check On Your Flight Status

We did not receive updates about our flights being cancelled until at least 24 hours after they were. Make sure ahead of your flight, you are checking to ensure it is still going according to schedule. You do not want to show up to learn that it was cancelled and you are now stuck.

5. Have A Credit Card With Travel Insurance

There are some great cards like Chase Saphire Preferred and Reserve, as well as Southwest Rapid Rewards Plus (here is a list to check out more options) that offer travel insurance. This can be a game changer when things go wrong.

Here are what they protect you against (per Nerdwallet):

Baggage delay. If your luggage doesn’t arrive when you do, you may receive a reimbursement to offset the costs of to buy new stuff.
Lost/damaged baggage. If your bags are lost or damaged by a carrier, or items have been stolen from your baggage, you may get reimbursed.
Trip delay. If your trip is delayed, you may receive monetary compensation to help cover meals, hotels, transportation and necessary purchases up to a certain amount per ticket.
Trip cancellation. If you need to cancel a prepaid, nonrefundable trip, you may receive compensation to offset the lost funds. It typically has to be considered one of the coverable reasons.
Trip interruption. If you miss a portion of your trip due to a covered reason, this benefit will reimburse you for any unused, prepaid, nonrefundable reservations (i.e., excursions, hotel nights).
Medical treatment. If you are hurt while traveling and require medical treatment, medical expenses may be covered up to a certain dollar amount.
Medical evacuation. If your illness or injury requires you to return home immediately for care, the insurance coverage through your card may cover the costs.
Travel accident insurance. In the case of accidental death or dismemberment, your credit card may provide coverage to you or to your beneficiary
Rental car insurance. This coverage provides protection to your rental car against theft and damage. Coverage may be primary or secondary to your personal auto insurance, depending on the card.