WEEKLY WHEATIES #2538
Booking Flights, Meta, AI, Travel
In this newsletter:
📝 Post: What’s the Smartest Way to Book Your Next Flight?
🗞️ In Case You Missed It: Meta Connect
🗞️ In Case You Missed It: AI Updates
🗞️ In Case You Missed It: Tech Headlines
😎 Pick of the Week: Travel Picks
📦 Featured Product: Travel Pillow and Phone Holder
📝 What’s the Smartest Way to Book Your Next Flight?
If you’ve been saving some of my travel picks over the last few months (or maybe planning a Skillcation) and potentially planning some trips, perhaps you are also planning to book a flight to get there. In the landscape of flying from one place to another, there are tons of apps and ways to go about booking your flight, that it can seem pretty overwhelming on where to start.
In general, I view flying as one of two extremes: you want to travel as inexpensively as possible and you don’t care when your flight is booked for; or your dates are pretty set and you just need a way to get there. The second option doesn’t mean you have to pay an exorbitant amount of money to get there, but in general, you will be paying a ‘convenience tax’ if you want to verify your arrival.
So, who to book through, and when to book?
Let’s start with the timing. Based on historical tracked data of some of the bigger booking sites, there are two big tips here. Typically, it’s better to book your flights on Tuesday or Wednesday. Then, it’s typically better to fly in or out of your destination on a Tuesday, Wednesday, or Saturday. Friday and Sunday are some of the most expensive travel days (because they are the most common).
If you’d like to play the game and want to wait and book the best price you can, or at least compare pricing for certain times of the year for travel, be sure to use Hopper. It does a great job showing the estimated travel costs based on when you may choose to travel. Google Flights has also been known to provide transparent price tracking based on dates and carriers.
However, while it may not be the cheapest alternative, booking direct with any airline in question may be the best option - as they will put you first for customer service should any major issue arise. By using Hopper and Google, you could find the best deal, then book directly with the airline in question. I typically suggest booking direct with the airline in question (American, Delta, JetBlue, Southwest, United).
But before you start looking up any flights, though, two major tips! First, use a VPN or Incognito Mode in your browser to avoid potential fare changes on the sites. Meaning, looking up airfare could potentially cause the price to continue to rise as you check other sites. Although many may say this doesn’t happen, it doesn’t hurt to be safe! Next, consider “alternative airports” in your area. An hour or so drive to a nearby airport could save you hundreds of dollars and sometimes even be quicker overall, as it may not have connecting flights or longer layovers.
Now, what if you don’t care when you arrive at your destination? Especially if you love to travel anywhere and everywhere, and may also travel alone. For these cases, I have two great suggestions. First, consider the GoWild! All You Can Fly Pass from Frontier Airlines. Frontier has a bad wrap from charging for anything and everything, but if you know what to expect and can work around it, this may be a great option - especially if you fly a lot. Next, consider this Surprising Travel Hack That Lets You Buy Other People’s Vacations - for those who didn’t purchase travel insurance and want to get *something* back for their loss.
There is one other way to fly that will be cheaper than anything else you can find. It’s known as Skiplagging (among others). And there’s even a site to help you book flights for this exact way of flying. HOWEVER, and I mean HOWEVER, I DO NOT suggest this way of flying. There are way more downsides than saving a few bucks. Essentially, a customer would book a flight from New Orleans to Boston, with a layover in New York. Instead of continuing on to Boston, they would just embark in New York, because that ticket was cheaper than a direct flight from New Orleans to New York.
This practice is technically not illegal, but the airlines can cancel your flights or ban you from their airlines. There’s already been a lawsuit over this, and they won. Not to mention, if the flight gets rerouted, you’re stuck somewhere else, nor can you check luggage. If you were very tight on money and only needed a one-way ticket somewhere on an airline you’d never fly again - sure, go for it. But remember, You're Going to Get Caught Skiplagging, and It’s Not Going to Be Pretty.
Once you do have your flights booked, consider some of these apps to track your flights and help on your travels:
Finally, check out a post I made last year on How to Travel Smart with Tech, or some great general tips on How to Make a Long-Haul Flight More Comfortable. If flying isn’t your thing, that’s okay, too - what about watching 23 Amazing Insects in Flight – Slow Motion!
🗞️ ICYMI: Meta Connect
At Meta Connect 2025, a few new updated pairs of Meta RayBan and Oakley Glasses were released, including the new Meta RayBan Display Glasses - AI-powered glasses with a type of AR lens featuring a mix of apps (messages, video calling, captions, maps, and more). Watch the Meta Connect Livestream on Facebook, or catch the 6 biggest announcements from The Verge. There were a bit of hiccups in the livestream with the demos, but that’s par for the course with any live demo. And if anything is a major issue, it will come out during the demos we hear about from all of the tech reviewers. So far, so good, though. Check out MKBHD’s review on YouTube for a bit more insight.
🗞️ ICYMI: AI Updates
In the AI space, Oracle and OpenAI Signed a $300 Billion Cloud Deal. However, don’t forget, Microsoft is still heavily invested, and they reached a new agreement with OpenAI that will change its corporate structure to the tune of $100 billion. Microsoft also looks to add Anthropic’s Claude to Office 365 as it shifts beyond its OpenAI reliance.
Through all of these changes on the backend of these LLMs, Duke and Harvard universities released a paper on How People Use ChatGPT. Compare that to Pew Research’s report on How Americans View AI and Its Impact on People and Society.
🗞️ ICYMI: Tech Headlines
Google Gemini is the top free iPhone app, while Google AI Edge Gallery takes over the Google Play Store. Google’s Chrome Browser also receives new AI features.
Cord Cutter Weekly shares a weekly updated list of streaming deals. Check it out as we kick off football season.
Gen Z is less likely to favor fully remote working compared with millennials and boomers. They also think iPods are cool again - so if you have any in storage, maybe see if your younger friends want to trade yard work for one?
AI software companies aren’t the only ones teaming up with competitors. Nvidia is looking to invest $5B in Intel to work together on AI infrastructure and PCs.
😎 POTW: Travel Picks
Still looking for somewhere interesting to visit? How about some of these:
12 Unique, Decidedly Cool, and Delightfully Unexpected Places to Visit
The Best State Parks for Hiking - (YouTube video on How To Walk Downhill or Uphill)
Looking down from your airplane window, wondering how different the world could look? Check out The True Size Of ...(a way to drag and compare the size of various countries). Or, see What The States Would Look Like If They Were Resized By Population.
📦 Featured Product
To go along with the travel post this week, how about two items you should consider for your next flight? A Travel Pillow with Neck Support and a Large Hood to help you sleep more comfortably, in case you weren’t able to snag that first-class lounger. And if you want to catch up on your most recent binge-worthy show, how about a Flight Flap Flexible Airplane Phone Holder? Mounting phones on an airplane is always tricky, and this is also useful in other locations.
