Your Guide to Scoring Holiday Season Flight Deals

 

It's that time of the year. Time to look for holiday flights. Whether you are looking to take a holiday trip or bring a child home for the holidays, you may be searching for a cheap flight or at least a travel deal. 

Twice in the last week, clients have asked me for help finding discounts on holiday flights. So here is your guide to finding those cheap flights or at least cheaper:

1. Start with google.com/flights to see what's available and the going rate. Try various airports, days, times etc. to see if you can move the needle. We are going to search for flights from New York to LAX. Look at the difference just by flying from JFK or Newark. 

Try using the date grid to check out different combinations of days to get a lower price. 

2. Be flexible - You may want to travel on certain days, but if you stay an extra day or leave a day early, you could save a lot of money. For example, over Thanksgiving, if you can stay an extra day and travel on Monday, December 2nd, the price for the flight may drop in half. A hack is using the flexible calendar on google flights. 

3. Check travel portals like Chase or Capital One. - Will the portals offer you a deal if you use points? And if you end up having to buy the flight, at least, you will earn 5x points on the purchase. Be sure to check the flexible dates calendar here too. 

Even if the prices aren't lower, this is one of the times, flexible points come in handy. You get a discount if you use your Chase Ultimate Rewards points because they are worth 1.5:1 with the Chase Sapphire Reserve credit card and 1.25:1 with the Chase Sapphire Preferred credit card. You can see with my Reserve card, I could pick up this $697 flight for 46,438 points. Still painful, but at least there is a discount. 

Worse comes to worse, you buy this flight through the portal and earn 5x points. You can also set an alert through google.com/flights or in the travel portal to let you know if the price drops. It's unlikely, but you never know. 

The bottom line is that the more flexible you can be on your dates and times, the more you can save. And remember, most people plan their travel about six weeks out. In the case of travel deals around the holidays, the early bird gets the worm. 

If you would like some help, please reach out. We love finding travel deals and planning amazing vacations using points and miles. 

Global Entry Is now FREE for kids

 

Great news! 

Global Entry is now FREE for kids under 18. Bad news, the membership price just went up to $120. 

So what is Global Entry? It is a program to expedite your journey through customs when you return to the United States. There is a separate Global Entry line with kiosks at 75 airports. You snap your photo, scan your passport and breeze right through the gate. 

If you have ever spent hours waiting in the customs line, you will appreciate the ease of this service. If you take 4+ international trips in 5 years, this is worth it especially if it's FREE. We will tell you how to get Global Entry for FREE in a bit. 

Global Entry includes TSA Precheck which will help you breeze through security for flights inside the US. You can also keep your shoes on and your laptop and toiletries in your bag which is a huge plus! 

Trusted Traveler has two other similar programs, NEXUS (expedited entry for Canada) and SENTRI (expedited entry for Mexico). 

Global Entry, Mobile Passport Control, and CLEAR are all US government programs that can help travelers move through the airport faster. 

• Global Entry is a Trusted Traveler Program that allows expedited entry into the US
• Mobile Passport Control is a free app that speeds up the customs declaration process
• CLEAR is an identity company that helps travelers quickly confirm their identity before security screening.

Global Entry Is now FREE for kids 

It's easy to apply through the Trusted Traveler website. You will need to complete your application with passport and driver's license information and then complete a second application for your child using their email address. At the prompt, you will enter your application ID and then click exempt from the fee for your child.  

You will still need to complete an interview as part of the process. Once you are conditionally approved, you will be prompted to schedule an interview. You may be able to schedule this process upon international arrival back into the US at the airport. If not, you will need to schedule the interview BEFORE you depart on your international trip. 

Global Entry Is now FREE for kids 

Besides saving money on Global Entry for kids, you can also get yours for FREE by using the right credit card to pay for it. Some of our favorite cards that include a Global Entry credit are:

• Chase Sapphire Reserve
• Capital One Venture X
• Capital One Venture 

As always though, be sure to choose the card that helps you reach your travel goals. We are here to help you with our Travel Coaching Program and 1:1 consulting. 

Amazing Bonus From One Of Our Favorite Cards

Get ready for some fantastic news, family travelers! The Chase Sapphire Preferred credit card just sweetened the deal, and we couldn't be more excited to share it with you!

Imagine this: a whopping 60,000 bonus points (that's at least $750 in FREE travel!) PLUS a $300 travel credit on travel purchases. And wait, there's more – a $50 hotel credit too! Add it all up, and you're looking at over $1,000 in FREE travel. How amazing is that for your next family adventure?

Over Water Bungalow in Moorea

But here's a little secret: with some savvy planning, you could stretch those points even further. Want to know how I used Chase Ultimate Rewards points to save a jaw-dropping $15,000 on a family trip to Tahiti? Just ask, and I'll share all the details!

Amazing Bonus From One Of Our Favorite Cards

Now, let's talk strategy. This card opens up a world of possibilities with its transfer partners. You can move your points to various airlines and hotel chains, giving you ultimate flexibility for your family's travel dreams.

Of course, there are a few things to keep in mind with this offer:

• You'll need to spend $4,000 in the first 3 months to earn the bonus.
• You can only earn a bonus on a Sapphire card once every four years.
• You can only hold one Chase Sapphire card at a time (either the Preferred or the Reserve).

Amazing Bonus From One Of Our Favorite Cards

Want to make sure this card aligns perfectly with your family's travel plans? Let's chat!

Book a one-on-one session with me, or join our Travel Coaching Program for even more insights. You'll learn all about maximizing points and miles, get a personalized credit card tracker, and join our monthly live coaching sessions.

Don't let this opportunity slip away – we never know how long these amazing offers will last. Let's start planning your next almost-free family adventure today!

Step #1 Towards Earning Your Southwest Companion Pass For 2025-26

 

It's the countdown towards earning the Southwest Companion Pass for 2025-26, yep, almost two full years. And I have challenged myself to help 25 people earn the pass. If you are ready, sign up here!  There is no cost to you, my coaching is totally FREE. 

Just in case you don't know what the pass is all about, here's a quick summary: 

• The Southwest Companion Pass is a BOGO flight pass for any flight, anywhere, anytime for you and one companion. No blackout dates, no restrictions. 

For comparison, Alaska Airlines offers its famous $99 companion pass which is good for one flight per year. 

American Airlines, British Airways, Aer Lingus and Delta Airlines offer a slightly different variation on the companion pass, but again it's just valid for one flight per year and costs up to $99. 

• Southwest is the ONLY airline that offers a companion pass for unlimited flights for up to two full years, it's an incredible deal. 

I have had the pass for 8 years and I estimate it has saved me thousands of dollars. I have used it to fly to Cuba, Costa Rica, Washington DC, New York, Puerto Rico, Florida, North Carolina, Washington State, Nashville, Chicago and so much more. 

• Southwest allows you to change your companion three times per calendar year. And your companion can be a partner, child, friend, family member or anyone else you would like to bring with you. 

So whether you have had the pass before or you are planning to earn it for the first time, let's talk about what we need to do now to get ready. You can also sign up to be one of the 25 people I am going to help for FREE to earn the pass. 

Step #1 Towards Earning Your Southwest Companion Pass For 2025-26

In very simple terms, in order to get the pass, we need to earn 135,000 Southwest points in a single calendar year. Once you earn the points, the companion pass will show up in your Southwest account and you can start using it immediately. The pass is good for the calendar year you earn it and the following year. Which means that if you earn the pass in January 2025, it is good for the rest of 2025 and 2026. 

That's the reason why we try to earn the pass as early in the year as possible. 

But if you are earning the pass for a second or third time or if you have received a Southwest credit card bonus before, you need to check a few things before you get started. 

1. IMPORTANT - Check the date that you last earned a Southwest point bonus. You can do that by logging into your Southwest account and checking your reward activity. You can see when I check my account, I earned a business card bonus in January 2023 and a personal card bonus in February 2023.  You can't apply for a new card until after those dates. So in my case, I cannot apply for another a Southwest Performance Business credit card until January 12th 2025 and I can't apply for another Southwest personal credit card until February 9th 2025.    

2. You earn 10,000 points on January 1st if you hold a Southwest Credit Card. These points are not valid for flights, but do count towards the companion pass. 

3. You can only hold ONE personal Southwest credit card at a time and you need to allow 30 days between closing the card you have and applying for another one. So now would be the right time to close your personal Southwest credit card if you plan to apply for another one in November. You can hold more than one Southwest Business credit card at a time so that's not an issue. 

4. Check your 5/24 status. Chase will only approve you for 5 credit cards every 24 months so confirm that you will eligible for a Southwest personal credit card. The business cards do not count towards 5/24. 

Step #1 Towards Earning Your Southwest Companion Pass For 2025-26

Make sure you do these steps so you are ready to hit the ground running in November to earn that pass. If you would like FREE coaching help, sign up to be one of the 25 people I am going to help earn the companion pass.